24 results about "Cycloheptane" patented technology

The present invention relates to a process for the preparation of (±)‑2‑exo‑(2‑methylbenzyloxy)‑1‑methyl‑4‑isopropyl‑7‑oxabicyclo[2.2.1]heptane of formula (I), any of its individual enantiomers or any non-racemic mixture thereof, comprising the steps of: (a) reacting (±)‑2‑exo‑hydroxy‑1‑methyl‑4‑isopropyl‑7‑oxabicyclo[2.2.1]heptane of formula (II), any of its individual enantiomers or any non-racemic mixture thereof, with a 2-methylbenzyl compound of formula (III), wherein X is a leaving group, in the presence of at least one base capable of forming water or a C1-C4 alkyl alcohol under the reaction conditions and at least one inert organic solvent, and (b) simultaneously removing water, C1-C4 alkyl alcohol or any mixture thereof from the reaction mixture.

Derivatives of Sabinene (1-isopropyl-4-methylenebicyclo[3.1.0]hexane, CAS No. 3387-41-5), as well as their synthesis and use in organoleptic applications, are described herein. The Sabinene derivatives include a compound having a general Formula (I), wherein --- is a single or a double bond; wherein if --- is a single bond, then Y is selected from the group consisting of CH2R1, CH=C(R2)R3, and (CH2)xCHR3R4; and OR5; wherein if --- is a double bond, then Y is O, N-OMe, or N-OEt; R is selected from the group consisting of H, C(O)-R6, and CH(R6)-OR5; R1 is selected from the group consisting of 1,3-dioxepan, 5-methyl-1,3-dioxolan-4-one, (CH=CH)x(CH2)nOH, (CH=CH)x(CH2)nCHO, CH(CH3)CO2Et, and CH(CH3)OH; R2 = H or Me; R3 is selected from the group consisting of CHO, CO2Et, (CH2)nOH, (CH2)nCHO, (CH2)nCN, and (CH2)nCO2Bu; and R4 is CHO or CH2OH; or R3 and R4 in combination form a dihydropyran, a tetrahydropyran, a tetrahydropyranol, a tetrahydropyranone, a dimethylcyclohexenone, or a dimethylcyclohexenol; R5 is selected from the group consisting of CH(CH3), CH(CH2CH3), C(CH3)CH3, and C(CH3)CH2CH3; R6 is selected from the group consisting of OMe and Me; x is an integer selected from 0 or 1; and n is an integer selected from 2 to 7; with the proviso that when --- is a double bond and Y is O, then R and R6 are not H.

The application provides a system and method for photocatalytic production of tetrahydrocycloheptane based on reactive distillation, and relates to the technical field of catalytic chemistry. The system comprises a backpack reactive distillation device, a solvent recovery and product purification column, and multiple heat exchangers. The backpack reactive distillation device comprises a distillation column and N photo reactors connected with the distillation column. The raw material norbornadiene, the side sampling stream of the distillation column, and the circulating stream taken from the bottom of the solvent recovery and product purification column are respectively introduced into each photo reactor from three paths. The reflux stream of the distillation column and the outlet streams of the N photo reactors are introduced into the distillation column. The crude product taken from the bottom of the distillation column is introduced into the solvent recovery and product purification column, the solvent recovery and product purification column separates and purifies tetrahydrocycloheptane and recovers the solvent, and high-efficiency and high-purity preparation of tetrahydrocycloheptane is realized.

This invention relates to azaheptanidine derivatives and their pharmaceutical uses, with specific structures shown in formula (I). It also relates to methods for preparing said compounds, pharmaceutical compositions, and their use as KRas G12C inhibitors in the treatment of cancer.

The invention belongs to the field of chemical synthesis, and particularly relates to a preparation method for synthesizing a beta-amino-acid ester compound from a cyano carbonyl compound. Specifically, after a cyano carbonyl compound shown as a formula A1 is generated through CO insertion catalyzed by palladium, dihalogenated chain alkane can be added after simple treatment without purification, a compound shown as a formula A is prepared through a halogen substitution reaction, and then a compound shown as a formula B is prepared through a cyano reduction reaction. Wherein R1 is cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl, X is halogen, and n is an integer from 1 to 8.

The invention provides a preparation method of spiro-structure sulfonium salt, which comprises the following steps: S1, carrying out nucleophilic substitution and oxidation reaction on (1R, 3S, 4S)-5-(2-bromo-1, 1, 2, 2-tetrafluoroethyl) bicyclo [2.2. 1] heptane-2, 3-diol and sodium hydrosulfite to obtain 2-(5, 6-dihydroxy bicyclo [2.2. 1] heptane-2-yl)-1, 1, 2, 2-tetrafluoroethane-1-sodium sulfonate, and carrying out a reaction on (1R, 3S, 4S)-5-(2-bromo-1, 1, 2, 2-tetrafluoroethyl) bicyclo [2.2. 1] heptane-2, 3-diol and sodium hydrosulfite to obtain (1R, 3S, 4S)-5-(2-bromo-1, 1, 2, 2- S2, carrying out ion exchange reaction on the 2-(5, 6-dihydroxy bicyclo [2.2. 1] heptane-2-yl)-1, 1, 2, 2-tetrafluoroethane-1-sodium sulfonate and triphenylsulfonium chloride salt to obtain triphenylsulfonium: 2-(5, 6-dihydroxy bicyclo [2.2. 1] heptane-2-yl)-1, 1, 2, 2-tetrafluoroethane-1-sulfonate; S3, carrying out ion exchange reaction on the triphenylsulfonium: 2-(5, 6-dihydroxy bicyclo [2.2. 1] heptane-2-yl)-1, 1, 2, 2-tetrafluoroethane-1-sulfonate and the triphenylsulfonium: 2-(5, 6-dihydroxy bicyclo [2.2. 1] heptane-2-yl)-1, 1, 2, 2-tetrafluoroethane-1-sulfonate to obtain 2, 2, 2-tetrafluoroethane-1-sulfonate and adamantanone formic acid are subjected to a ketal reaction under the acidic condition, and the spiro-structure sulfonium salt is obtained.

The invention provides a preparation method of an enantiomer impurity of a key intermediate of meloabalin besylate, the chemical name of the enantiomer impurity of the key intermediate of meloabalin besylate is (1S, 5R)-3-ethyl-bicyclo [3.2. 0] heptane-3-ene-6-ketone, racemate 3-ethyl-bicyclo [3.2. 0] heptane-3-ene-6-ketone is used as a raw material, and the enantiomer impurity of the key intermediate of meloabalin besylate is prepared through a one-pot method. And adding reductase into the racemate to carry out reduction reaction, adding acid anhydride to react again after the reduction reaction, and carrying out alkali washing to obtain the enantiomer impurity of the meloabalin besylate key intermediate. According to the invention, a specific enzyme is found, the (1R, 5S)-3-ethyl-bicyclo [3.2. 0] heptane-3-ene-6-ketone can be specifically reduced, the treatment process is simple, the treatment capacity is large, expensive HPLC (High Performance Liquid Chromatography) chiral resolution is avoided, and the synthesis cost is greatly reduced.

The invention discloses a preparation method of a light-induced acid generator (4-(cyclohexyl sulfonyl) phenyl) diphenyl sulfonium and bis-trifluoroethoxy bicycloheptane-2-sulfonate) for photoresist. The preparation method is used for synthesizing the light-induced acid generator (4-(cyclohexyl sulfonyl) phenyl) diphenyl sulfonium and bis-trifluoroethoxy bicycloheptane-2-sulfonate). The invention further discloses a preparation method of the light-induced acid generator (4-(cyclohexyl sulfonyl) phenyl) diphenyl sulfonium and bis-trifluoroethoxy bicycloheptane-2-sulfonate). According to the synthesis process, fluorobenzene is used as a reaction raw material, so that the operation procedure is simplified, the product quality is improved, the production cost is reduced, and the market competitiveness is improved; the use of highly toxic raw materials is avoided, the environmental pollution is reduced, and the method is an economical and environment-friendly synthesis process route; the synthesis process is mature in route technology, low in investment and simple in flow, the production process is simplified, potential safety hazards are reduced, and production safety can be ensured.

The invention discloses a method for preparing (9S)-6, 7, 8, 9-tetrahydro-9-hydroxy-5H-cycloheptane [b] pyridine-5-ketone through catalysis of alcohol dehydrogenase, and cycloheptane [b] pyridine-5, 9-diketone is used as a raw material, alcohol dehydrogenase is used as a catalyst, and a target product is generated through reaction. The alcohol dehydrogenase is derived from Acetobacter aceti, the amino acid sequence of the alcohol dehydrogenase is as shown in SEQ ID NO. 1, and the nucleotide sequence for coding the alcohol dehydrogenase is as shown in SEQ ID NO. 2. According to the method, (9S)-6, 7, 8, 9-tetrahydro-9-hydroxy-5H-cycloheptane [b] pyridine-5-ketone is prepared under the optimized alcohol dehydrogenase catalytic reaction condition, the substrate concentration is 50 g / L, the reaction conversion rate is larger than 99%, the product chiral purity is larger than 99.5% ee, and good industrial application value is achieved.

The invention discloses a purification method of low-purity dimercaptoethyl sulfide, which comprises the following steps: step 1, sequentially adding triphenylphosphine, acetic acid and distilled water into dimercaptoethyl sulfide, uniformly mixing, and reacting at 85 DEG C for 2 hours; step 2, cooling the mixture after the reaction in the step 1 to room temperature (20-25 DEG C), and washing with water until the pH value of the system is neutral; and step 3, rectifying the liquid obtained in the step 2 under the conditions of 0.5 mbar and 120 DEG C to obtain purified dimercaptoethyl sulfide. According to the technical scheme, triphenylphosphine is adopted as a reducing agent, acetic acid and distilled water are used for providing protons and a weak acid environment, 1, 2, 5-trithiocycloheptane is specifically reduced, then through a simple rectification mode, dimercaptoethyl sulfide with the purity larger than 97% can be obtained, reutilization of expired raw materials is achieved, resources are saved, and the production cost is saved for enterprises.

Disclosed are salt forms and crystals of a series of tetrahydrocycloheptaindazole compounds and methods for their preparation, in particular the use of the salt forms and crystals of the compound of formula (I) in the manufacture of medicaments for treating related diseases. [Formula 1] JPEG2024546191000044.jpg68169

This invention provides a method for preparing an intermediate of retinoic acid, belonging to the field of compound preparation technology. The preparation method includes the following steps: (1) compound M6 and R (1) The tert-butylsulfinamide reaction yields compound M6A; (2) Compound M6A undergoes a reduction reaction under the action of a reducing agent to yield (9R)-6,7,8,9-tetrahydro-9-hydroxy-5H-cycloheptane[b]pyridine-5-amine. The preparation method of the present invention avoids the use of high-pressure hydrogenation and ammonia, resulting in less environmental pollution and a higher yield, which facilitates subsequent industrial production.

Disclosed are dimethylbicycloheptenyl and dimethylbicycloheptanyl derivatives possessing green-galbanum and fruity-pineapple odor notes.

The present invention discloses a process for the synthesis of a compound according to formula (I) or a pharmaceutically acceptable salt thereof, wherein - R is a bicycloalkyl group, preferably an unsubstituted bicycloalkyl group. The process the following steps, preferably performed sequential in time, I. asymmetric ring opening of a carbic anhydride, preferably cis-5-Norbornene-endo-2,3-dicarboxylic anhydride or (3aR,4S,7R,7aS)-3a,4,7,7a-tetrahydro-4,7- methanoisobenzofuran-1,3-dione, yielding (1S,2R,3S,4R)-3- (methoxycarbonyl)bicyclo[2.2.1]hept-5-ene-2-carboxylic acid, II. epimerizing of (1S,2R,3S,4R)-3-(methoxycarbonyl)bicyclo[2.2.1]hept-5-ene-2- carboxylic acid yielding (1S,2R,3R,4R)-3-(methoxycarbonyl)bicyclo[2.2.1]hept-5-ene- 2-carboxylic acid, III. hydrogenating (1S,2R,3R,4R)-3-(methoxycarbonyl)bicyclo[2.2.1]hept-5-ene-2- carboxylic acid yielding (1R,2R,3R,4S)-3-(methoxycarbonyl)bicyclo[2.2.1]heptane-2- carboxylic acid, IV. decarboxylating (1R,2R,3R,4S)-3-(methoxycarbonyl)bicyclo[2.2.1]heptane-2- carboxylic acid yielding methyl (1S,2S,4R)-bicyclo[2.2.1]heptane-2-carboxylate, V. hydrolysing methyl (1S,2S,4R)-bicyclo[2.2.1]heptane-2-carboxylate yielding (1S,2S,4R)-bicyclo[2.2.1]heptane-2-carboxylic acid, VI. coupling (1S,2S,4R)-bicyclo[2.2.1]heptane-2-carboxylic acid with a benzylamine, preferably substituted with a substituent selected from the group consisting of heteroatoms, in particular F, SF5, CF3 or OCF3, or an alkyl group, in particular an ethyl-, methyl- or propyl-group, yielding a compound according to formula (I), and VII. optionally crystallising of the compound according to formula (I).

This application relates to the field of medicinal chemistry, specifically to a derivative of ligustilide-7-aminocarbamate-4'-substituted aminopropyl ether, its preparation method, and its application. Addressing the shortcomings of ligustilide in AD treatment, this application utilizes previous studies to demonstrate strong eeAChE and huACh inhibitory activity, strong inhibition of self-induction, and Cu... 2+ Induced Aβ 1‑42 Aggregation activity, significantly reduced Aβ 25‑35 The lead compound, scutellarin aglycone-4′-L-amino acid carbamate, which induces tau hyperphosphorylation and significantly improves learning and memory impairment in scopolamine-induced AD model mice, is used to introduce histamine H at the 7-position of its structure. 3 By using the key structural fragment (3-methylpiperidinyl) or cycloheptane group of the receptor antagonist, a cholinesterase inhibitor and histamine H2 receptor antagonist can be obtained. 3 Multi-targeted ligand derivatives with better anti-AD properties through receptor antagonistic synergistic mechanism.

The present invention relates to a crystalline form of N-(4-(4-amino-6-ethynyl-5-(quinolin-3-yl)-7H-pyrrolo [2, 3-d] pyrimidin-7-yl) bicyclo [2.2. 1] heptane-1-yl)-5-methylpyrazine-2-carboxamide (TAS3351), a compound having an EGFR inhibitory effect, and an acid. The crystalline form has superior physical properties, including stability, hygroscopicity, and oral absorbability. The crystal form has a peak at a specific diffraction angle (2 [theta] + / -0.2 DEG) in a powder X-ray diffraction spectrum.

The present invention relates to a process for the preparation of (+ / -)-2-exo-(2-methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo [2.2. 1] heptane of formula (I), any of its individual enantiomers or any of its non-racemic mixtures, the process comprises the steps of (a) reacting (+ / -)-2-ex-hydroxy-1-methyl-4-isopropyl-7-oxabicyclo [2.2. 1] heptane of formula (II), any its individual enantiomer or any non-racemic mixture thereof with formula (III) wherein X is a leaving group the 2-methylbenzyl compound is reacted in the presence of at least one base capable of forming water or C1-C4 alkyl alcohol under reaction conditions and at least one inert organic solvent, and (b) water, C1-C4 alkyl alcohol or any mixture thereof are simultaneously removed from the reaction mixture.

This invention relates to compounds of formula (Ia), or pharmaceutically acceptable salts or hydrates thereof, wherein: groups X-Y are -NHSO2- or -SO2NH-; R1 is H or alkyl; R2 is selected from COOH and tetrazolyl; R3 is selected from H, Cl and alkyl; R4 is selected from H, Cl and F; R5 is selected from H, alkyl, alkynyl, alkenyl, haloalkyl, SO2-alkyl, Cl, alkoxy, OH, CN, hydroxyalkyl, alkylthio, heteroaryl, cycloalkyl, heterocycloalkyl and haloalkoxy; R6 is H; R7 is selected from H, CN, haloalkyl, Cl, F, SO2-alkyl, SO2NR 13 R 14 Optionally substituted heteroaryl and alkyl groups; R8 is selected from H, alkyl, haloalkyl, and halogen; R9 is H, C1-C3 alkyl, or halogen; R 10 and R 11 Together with the nitrogen atoms to which they are attached, they form an azircyclic heptyl group, wherein (a) the azircyclic heptyl group is substituted with one or more substituents, or (b) one or two carbons of the azircyclic heptyl group are substituted with a group selected from O, NH, S and CO, and the azircyclic heptyl group is optionally further substituted; or R 10 and R 11 Together with the nitrogen atoms to which they are attached, they form an azircyclic butyl, pyrrolidinyl, or piperidinyl group, wherein (a) the azircyclic butyl, pyrrolidinyl, or piperidinyl group is substituted by one or more substituents, or (b) one or two carbon atoms of the azircyclic butyl, pyrrolidinyl, or piperidinyl group are substituted by a group selected from NH, S, and CO; or R 10 and R 11 Together with the nitrogen atoms to which they are attached, they form 8-, 9-, or 10-membered bicyclic heterocyclic alkyl groups, wherein one or two carbons of the bicyclic heterocyclic alkyl ring are optionally replaced by groups selected from O, NH, S, and CO, and the bicyclic heterocyclic alkyl group is optionally substituted; or R 10 and R 11 Together with the nitrogen atoms to which they are attached, they form 6- to 12-membered bicyclic groups containing spirocyclic carbon atoms, wherein one or both carbons of the bicyclic group are optionally replaced by a group selected from O, NH, S, and CO, and the bicyclic group is optionally substituted or optionally fused with a 5- or 6-membered aryl or heteroaryl group; R 13 and R 14 Each compound is independently H or alkyl. Other aspects of the invention relate to the use of such compounds in the field of immuno-oncology and related applications.

The invention belongs to the technical field of organic synthesis, and particularly provides a preparation method of (R, S)-2-[[5-(9-fluorenylmethoxycarbonyl amino) dibenzo [a, d] cycloheptane-2-yl] oxygen] acetic acid, which comprises the following steps: S1, reacting 2-(5-oxysubunit dibenzo [a, d] cycloheptane-2-oxy) acetic acid with formamide to generate 2-(5-formamido dibenzo [a, d] cycloheptane-2-oxy) acetic acid; step S2, removing a formyl protecting group from the 2-(5-formylamino dibenzo [a, d] cycloheptane-2-oxyl) acetic acid, so as to generate 2-(5-amino dibenzo [a, d] cycloheptane-2-oxyl) acetate, and carrying out a reaction on the 2-(5-formylamino dibenzo [a, d] cycloheptane-2-oxyl) acetate and the 2-(5-formylamino dibenzo [a, d] cycloheptane-2-oxyl) acetate, and S3, enabling the 2-(5-aminodibenzo [a, d] cycloheptane-2-oxy) acetate to react with an Fmoc introduction reagent, so as to generate the (R, S)-2-[[5-(9-fluorenylmethoxycarbonyl amino) dibenzo [a, d] cycloheptane-2-yl] oxy] acetic acid. According to the preparation method disclosed by the embodiment of the invention, reagents which are low in cost and easy to obtain are selected, and dangerous reagents are prevented from being used, so that the preparation cost is reduced, and the reaction safety coefficient is also improved.

The invention relates to the technical field of adhesives, and discloses a polyurethane-based polymer adhesive and a preparation method thereof, the adhesive is prepared by taking polyether glycol as a soft segment and a diisocyanate monomer as a hard segment, and carrying out cross-linking polymerization reaction with functional additives and the like under the action of a catalyst, wherein the functional additive is prepared by grafting a macromolecular modifier with a diphenyl ether-cycloheptane alternate connection structure on the surface of vermiculite, and the macromolecular modifier can participate in chain extension polymerization of polyurethane, so that the vermiculite and the polyurethane have good interface bonding property, and by utilizing the lamellar structure of the vermiculite, the functional additive can be used for preparing the polyurethane composite material. According to the present invention, the high-molecular modifier is added to the polyurethane adhesive to form the stable physical barrier layer, such that the dissipation of the adhesive thermal degradation product can be effectively retarded, and the high-molecular modifier structure contains rich rigid rings, silicon-oxygen bonds and ether bonds so as to further enhance the high temperature resistance of the polyurethane adhesive, and further enhance the adhesion property of the polyurethane adhesive.