3-alkoxy-1,1-dialkylthiol propylene derivative and synthetic method

A technology of dialkylthiopropene and synthesis method, applied in the direction of organic chemistry and the like, can solve the problems of low atom utilization rate, few alkenes, and narrow application range of substrates, so as to avoid pre-functionalization, simplify synthesis steps, and achieve application scope. wide effect

Active Publication Date: 2018-06-12
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the reported Friedel-Crafts alkylation reactions are all sp of aromatics or heteroaromatics 2 Alkylation of C-H bonds, while the alkylation of alkenes is less reported
It can be mainly divided into two categories: (1) The classic Friedel-Crafts reaction is used to achieve the alkylation reaction of alkenes, but halogenated hydrocarbons or alkenes are needed as alkylating agents, but the utilization rate of atoms in this type of reaction is low or The substrate has a narrow scope of application, and only aryl olefins can be used as alkylating reagents (Chem.Eur.J.2011,17,8290; Chem.Eur.J.2012,18,15158; Chem.Commun.2014,50 ,6337); (2) Alkylation of alkenes by transition metal-catalyzed C–H bond functionalization

Method used

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  • 3-alkoxy-1,1-dialkylthiol propylene derivative and synthetic method
  • 3-alkoxy-1,1-dialkylthiol propylene derivative and synthetic method
  • 3-alkoxy-1,1-dialkylthiol propylene derivative and synthetic method

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028]

[0029] The specific process is: weigh dithioketene 2a (111.2 mg, 0.5 mmol), FeCl 3 (4.1mg, 0.025mmol), DABCO·6H 2 O (11.0mg, 0.05mmol) was added to a 25mL sealed tube with a branch, 1,4-Dioxane (3mL) and DTBP (219.2mg, 1.5mmol) were added under a nitrogen atmosphere, and placed in an oil bath at 130°C React in 24h. After the reaction is complete, cool to room temperature, filter with diatomaceous earth, and rotary evaporate under reduced pressure to remove the solvent, then column chromatography (petroleum ether (60-90°C) / ethyl acetate: 8:1, v / v) to obtain a light yellow Solid product 1a (122.5 mg, yield 80%). The target product was confirmed by NMR and high-resolution mass spectrometry.

Embodiment 2

[0031]

[0032] The reaction steps and operations are the same as in Example 1, except that the dithioketene added to the reaction system is 2b (150.0 mg, 0.5 mmol). The reaction was stopped, and the target product 1b (146.0 mg, yield 76%) was obtained as a light yellow solid after post-processing. The target product was confirmed by NMR and high-resolution mass spectrometry.

Embodiment 3

[0034]

[0035] The reaction steps and operations are the same as those in Example 1, except that the dithioketene added to the reaction system is 2c (118.0 mg, 0.5 mmol). The reaction was stopped, and the target product 1c (128.0 mg, yield 79%) was obtained as a light yellow solid after post-processing. The target product was confirmed by NMR and high-resolution mass spectrometry.

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Abstract

The invention discloses a 3-alkoxy-1,1-dialkylthiol propylene derivative and a synthetic method thereof. The synthetic method comprises the following steps: taking easily prepared S-acetals with structural diversity and multiple reaction centers as raw materials, under the promotion of an iron salt, carrying out an oxidative coupling reaction with simple ether, thereby synthesizing a series of different structures of 3--alkoxy-1,1-dialkylthiol propylene derivatives, wherein the product can be further converted into a functional product. The method is highly available in raw materials, simple and convenient to operate and high in reaction efficiency, and the functional groups are of diversity.

Description

technical field [0001] The invention relates to a method for preparing four-substituted olefin compound 3-alkoxy-1,1-dialkylthiopropene derivatives. 3-alkoxy-1, 1-Dialkylthiopropene derivatives. Compared with the existing synthetic methods of multi-substituted olefin derivatives, the present invention has easy-to-obtain raw materials, simple and convenient operation, high yield, and uses iron salt as a catalyst, which is environmentally friendly; and can avoid pre-functionalization of substrates, and has atomic High economical features. Background technique [0002] Multi-substituted alkenes are important structural units that widely exist in natural products and drug molecules. For example (Z)-Tamoxifen is currently the most important drug used clinically for the prevention and treatment of breast cancer. and Vioxx for the treatment of hypertrophic osteoarthritis and rheumatoid arthritis. Alkylation of olefins is an important synthetic method for the preparation of mul...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D409/06C07D319/12C07D405/04
CPCC07D319/12C07D405/04C07D409/06
Inventor 余正坤汪全南吴苹
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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