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A kind of synthetic method of six-membered carbocyclic derivatives

A six-membered carbocyclic ring, synthesis method technology, applied in the direction of organic chemistry methods, chemical instruments and methods, preparation of organic compounds, etc., can solve the problems of harsh reaction conditions, low reaction stability, complex reaction steps and so on

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 aims to propose a synthetic method for six-membered carbocyclic derivatives, which solves the technical problems of harsh reaction conditions, complex reaction steps, and low reaction stability in the prior art.

Method used

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  • A kind of synthetic method of six-membered carbocyclic derivatives
  • A kind of synthetic method of six-membered carbocyclic derivatives
  • A kind of synthetic method of six-membered carbocyclic derivatives

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preparation example Construction

[0027] The embodiment of the present invention proposes a method for synthesizing six-membered carbocyclic derivatives, comprising the following steps:

[0028] Under the protection of an inert gas, in an organic solvent, the compound of the formula (I-1), the compound of the formula (II) and the compound of the formula (III) react under the action of a catalyst and a cocatalyst to obtain a compound having the structure of the formula (IV-1) Six-membered carbocyclic derivatives;

[0029] Or, under the protection of an inert gas, in an organic solvent, the compound of the formula (I-2), the compound of the formula (II) and the compound of the formula (III) react under the effect of a catalyst and a cocatalyst to obtain a compound of the formula (IV-2) Six-membered carbocyclic derivatives of the structure;

[0030] The catalyst is an organic rare earth compound; the cocatalyst is a boron salt;

[0031]

[0032] X is C or N;

[0033] When X is N, R 1 , R 2 each independen...

Embodiment 1

[0059] The chemical reaction formula is as follows, including the following steps:

[0060]

[0061] Under nitrogen atmosphere, the cocatalyst [Ph 3 C][B(C 6 f 5 ) 4 ] (18.45mg, 0.02mmol) was dissolved in chlorobenzene (1mL), slowly added dropwise to the stirred catalyst (η 5 -C 5 Me 4 -C 5 h 3 NCH 3 )Sc(CH 2 SiMe 3 ) 2 (9.8mg, 0.02mmol) in chlorobenzene (1mL) solution. Add 2-methylanisole 1a (122mg, 1.0mmol), 1,4-pentadiene 2 (102mg, 1.5mmol) and styrene 2 (104mg, 1.0mmol) into the solution in sequence, and magnetically After stirring for 6h, TLC monitored the progress of the reaction. After the reaction, use n-hexane as the mobile phase, separate and purify by column chromatography to obtain the corresponding catalytic product, colorless liquid 4aa, with a yield of 90%.

[0062] NMR characterization is as follows: 1 H NMR (400MHz, CDCl 3 )δ7.26-7.21(m,2H),7.18(d,J=6.9Hz,2H),7.15-7.10(m,3H),6.88–6.77(m,2H),3.78(s,3H),2.93 (ddd, J=12.5,8.0,3.2Hz,1H),2.77(qd...

Embodiment 2

[0064] The chemical reaction formula is as follows, including the following steps:

[0065]

[0066] Under nitrogen atmosphere, the cocatalyst [Ph 3 C][B(C 6 f 5 ) 4 ] (18.45mg, 0.02mmol) was dissolved in chlorobenzene (1mL), slowly added dropwise to the stirred catalyst (η 5 -C 5 Me 4 -C 5 h 3 NC 6 h 5 )Sc(CH 2 SiMe 3 ) 2 (10.1mg, 0.02mmol) in chlorobenzene (1mL) solution. 2-Ethyl-6-picoline 1a (121mg, 1.0mmol), 1,4-pentadiene 2 (102mg, 1.5mmol) and 1,1-stilbene 2 (180mg, 1.0mmol) were added sequentially The solution was magnetically stirred at 60° C. for 4 h, and the reaction progress was monitored by TLC. After the reaction, using n-hexane / ethyl acetate (95:5) as the mobile phase, separation and purification by column chromatography gave the corresponding catalytic product, a colorless liquid 4bb, with a yield of 83%.

[0067] NMR characterization is as follows: 1H NMR (400MHz, CDCl3) δ7.49 (t, J = 7.6Hz, 1H), 7.29–7.20 (m, 4H), 7.20–7.09 (m, 5H), 7.07 (d,...

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Abstract

The invention provides a method for synthesizing six-membered carbocyclic derivatives, which belongs to the technical field of organic synthesis. The synthesis method comprises the following steps: under the protection of an inert gas, in an organic solvent, the compound of formula (I-1), the compound of formula (II) and the compound of formula (III) react under the action of a catalyst and a co-catalyst to obtain a compound having the formula (Ⅳ-1) Six-membered carbocyclic derivatives of compound structure; 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 2 independently selected from substituted or unsubstituted C 1 -C 10 Alkyl; R 3 and R 4 Each is independently selected from substituted or unsubstituted alkyl groups. 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 method for synthesizing six-membered carbocyclic derivatives. 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 cycloisomerization reaction...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/127C07D213/16C07C41/30C07C43/21C07C43/225C07C209/68C07C211/48
CPCC07B2200/07C07C41/30C07C209/68C07D213/127C07D213/16C07C2601/14C07C43/21C07C43/225C07C211/48
Inventor 陈延辉汤斌姜涛柳春丽
Owner TIANJIN UNIV OF SCI & TECH
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