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A kind of synthetic method of carbocyclic derivative substituted by unsaturated double bond

A synthesis method and unsaturated technology, which are applied in the synthesis field of carbocyclic derivatives, can solve the problems of low reaction stability, harsh synthesis reaction conditions, complicated reaction steps and the like

Active Publication Date: 2021-10-26
TIANJIN UNIV OF SCI & TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The present invention provides a simple and efficient synthetic method for preparing carbocyclic derivatives substituted by unsaturated double bonds, so as to solve the technical problems of harsh synthetic reaction conditions, complicated reaction steps and low reaction stability in the prior art.

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  • A kind of synthetic method of carbocyclic derivative substituted by unsaturated double bond
  • A kind of synthetic method of carbocyclic derivative substituted by unsaturated double bond
  • A kind of synthetic method of carbocyclic derivative substituted by unsaturated double bond

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preparation example Construction

[0031] A method for synthesizing carbocyclic derivatives substituted by unsaturated double bonds, comprising the steps of:

[0032] Under the protection of an inert gas, in an organic solvent, the compound of the formula (I-1) reacts with the compound of the formula (II) under the action of a catalyst and a cocatalyst to obtain a carbocyclic ring substituted with a double bond having the structure of the compound of the formula (III-1) Compounds;

[0033] Or, under the protection of an inert gas, in an organic solvent, the compound of the formula (I-2) reacts with the compound of the formula (II) under the action of a catalyst and a cocatalyst to obtain a compound having a structure of the formula (III-2) substituted with a double bond Carbocyclic compounds;

[0034] The catalyst is an organic rare earth compound; the cocatalyst is a boron salt;

[0035]

[0036] in,

[0037] X is C or N;

[0038] When X is N, R 1 , R 2 each independently selected from a hydrogen atom...

Embodiment 1

[0073] A method for synthesizing carbocyclic derivatives substituted by unsaturated double bonds, comprising the steps of:

[0074]

[0075] Under nitrogen atmosphere, the cocatalyst [Ph 3 C][B(C 6 f 5 ) 4 ] (18.5mg, 0.02mmol) was dissolved in chlorobenzene (1mL) to obtain a cocatalyst solution, and the catalyst (η 5 -C 5 Me 4 -C 5 h 3 NC 6 h 5 )Sc(CH 2 SiMe 3 ) 2 (THF) (10.1 mg, 0.02 mmol) was dissolved in chlorobenzene (1 mL) to obtain a catalyst solution. Then 2-methylanisole 1a (122.2mg, 1.0mmol) and 1,5-hexadiene 2a (205mg, 2.5mmol) were added to the reaction system, stirred magnetically at 70°C for 4h, and analyzed by thin layer chromatography ( TLC) to monitor the progress of the reaction. After the reaction, using n-hexane as the mobile phase, separation and purification by column chromatography gave the corresponding catalytic product, a colorless liquid 3a, with a yield of 71%.

[0076] NMR characterization is as follows: 1 H NMR (400MHz, CDCl 3 )...

Embodiment 2

[0078] A method for synthesizing carbocyclic derivatives substituted by unsaturated double bonds, comprising the steps of:

[0079]

[0080] Under nitrogen atmosphere, the cocatalyst [Ph 3 C][B(C 6 f 5 ) 4 ] (18.5mg, 0.02mmol) was dissolved in chlorobenzene (1mL) to obtain a cocatalyst solution, and the catalyst ((η 5 -C 5 Me 4 -C 5 h 3 NBr)Sc(CH 2 SiMe 3 ) 2 (THF) (11.2mg, 0.02mmol) was dissolved in chlorobenzene (1mL) solution to obtain a catalyst solution, the cocatalyst solution was slowly added dropwise to the stirred catalyst solution, and then 2,3-benzofuran 1b (1.0mmol ) and 1,5-hexadiene 2a (123mg, 1.5mmol) were added to the reaction system, magnetically stirred at 60°C for 4h, and the reaction progress was monitored by TLC. After the reaction, using n-hexane as the mobile phase, separation and purification by column chromatography gave the corresponding catalytic product, a colorless liquid 3ba, with a yield of 64%.

[0081] NMR characterization is as ...

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Abstract

The invention provides a method for synthesizing carbocyclic derivatives substituted with unsaturated double bonds, which belongs to the technical field of synthesis. The synthesis method comprises: under the protection of an inert gas, in an organic solvent, the compound of the formula (I-1) reacts with the compound of the formula (II) under the action of a catalyst and a cocatalyst to obtain a double bond having the structure of the compound of the formula (III-1) Substituted carbocyclic compounds; the catalyst is an organic rare earth compound; the cocatalyst is a boron salt; wherein, X is C or N; when X is N, R 1 , R 2 each independently selected from a hydrogen atom, substituted or unsubstituted C 1 -C 10 Alkyl; when X is C, R 1 independently selected from substituted or unsubstituted C 1 -C 6 Alkoxy; R 3 for C 1 -C 10 substituted or unsubstituted alkyl; n=1 or 2. The method has a wide range of raw materials, mild reaction conditions and good atom economy, and is widely used in the chemical and pharmaceutical fields.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a synthesis method of carbocyclic derivatives substituted with unsaturated double bonds. Background technique [0002] Due to the wide range of biological activities of carbocyclic compounds, their simple and efficient synthesis methods have attracted much attention. At present, the synthesis method of carbocyclic compounds substituted with unsaturated double bonds mainly utilizes metal-catalyzed cycloisomerization of dienes or enynes. For example, in 1998, RajanBabu et al. (J.Am.Chem.Soc.1998,120(31):8007-8008.) reported that 1,6-diene intramolecular cyclization reaction was realized under the action of palladium catalysis , to generate carbocyclization products of five-membered rings and six-membered rings, but the reaction conditions are harsh. In 2007, Carboni et al. (Organic letters.2007,9(9):1717-1720.) used zero-valent palladium as a catalyst to catalyze the cy...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/127C07D213/16C07C209/68C07C211/48C07D307/79C07C41/30C07C43/215
CPCC07B2200/07C07C41/30C07C209/68C07D213/127C07D213/16C07D307/79C07C2601/08C07C2601/14C07C211/48C07C43/215
Inventor 陈延辉汤斌姜涛柳春丽
Owner TIANJIN UNIV OF SCI & TECH
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