Method for preparing polysubstituted distal-end allyl ketone derivative

A technology for allyl ketone and derivatives, which is applied in the field of preparation of multi-substituted distal allyl ketone derivatives, can solve the problems of large equipment requirements, harsh conditions, low yield and the like, and achieves low cost and mild reaction conditions. , the effect of high research value

Active Publication Date: 2018-05-01
HARBIN INST OF TECH
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

[0005] The purpose of the present invention is to solve the problem that most of the existing methods for synthesizing multi-substituted distal allyl ketone derivatives by ring-opening of ring alcohols use high-temperature heating systems, high energy consumption, harsh conditions, large requirements for equipment, and low yields , providing a preparation method of multi-substituted distal allyl ketone derivatives

Method used

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  • Method for preparing polysubstituted distal-end allyl ketone derivative
  • Method for preparing polysubstituted distal-end allyl ketone derivative
  • Method for preparing polysubstituted distal-end allyl ketone derivative

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specific Embodiment approach 1

[0013] Specific embodiment 1: In this embodiment, a method for preparing a multi-substituted distal allyl ketone derivative comprises the following steps:

[0014] Dissolve tertiary cyclic alcohol derivatives, unsaturated ethylenic compounds, bases and photocatalysts in an organic solvent in a nitrogen atmosphere at room temperature, mix them evenly, and then place them under a blue LED light for photoreaction. Separation and purification by column chromatography, the obtained product is a multi-substituted distal allyl ketone derivative; the molar ratio of unsaturated ethylenic compound, tertiary cyclic alcohol derivative, base and photocatalyst is 2:1:2.5:0.5;

[0015] Wherein the chemical structural formula of tertiary cyclic alcohol derivative is:

[0016] The chemical structural formula of unsaturated ethylenic compounds is:

[0017] The chemical structural formula of the photocatalyst is:

[0018] Among them, R 1 , R 2 and R 3 is alkyl, alkoxy or halogen, and ...

specific Embodiment approach 2

[0023] Specific embodiment 2: The difference between this embodiment and specific embodiment 1 is that the unsaturated ethylenic compound is α, β unsaturated ester substituted by methyl, α, β unsaturated ester substituted by ethyl, α, β substituted by nitro Unsaturated esters or cyano-substituted α, β unsaturated esters. Others are the same as the first embodiment.

specific Embodiment approach 3

[0024] Specific embodiment three: the difference between this embodiment and specific embodiment one or two is that the three-level cyclic alcohol derivatives are three-membered cyclic alcohols, four-membered cyclic alcohols, five-membered cyclic alcohols, twelve-membered cyclic alcohols, ortho polycyclic alcohols Alkyl substituted cyclic alcohols or ortho aryl substituted cyclic alcohols. Others are the same as those in Embodiment 1 or 2.

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Abstract

The invention relates to a method for preparing a polysubstituted distal-end allyl ketone derivative. An object of the invention is to provide the method for preparing the polysubstituted distal-end allyl ketone derivative. The method comprises the steps of dissolving a third-grade cyclitol derivative, an unsaturated olefin compound and a photocatalyst in an organic solvent in a nitrogen gas atmosphere at room temperature, carrying out uniform mixing, carrying out a lighting reaction under a blue LED (light emitting diode) lamp, carrying out rotary evaporation to remove the solvent, then, carrying out silica-gel column chromatographic separation and purification, thereby obtaining a product, i.e., the polysubstituted distal-end allyl ketone derivative. According to the method provided by the invention, the reaction can be carried out at normal temperature under normal pressure the reaction conditions are mild, and the yield can reach 80%; and the method has the advantages of simplicityin operation, no pollution, safety, environment-friendliness and low cost. The invention is applied to the field of organic synthesis.

Description

technical field [0001] The invention relates to a preparation method of a multi-substituted distal allyl ketone derivative. Background technique [0002] Cycloalcohols widely exist in biologically active natural products and drug molecules, and are also important raw material intermediates for many chemical products and other natural products. According to literature reports, through a series of transformation reactions, various important Intermediates of chemical raw materials, such as unsaturated distal diketone ketone compound 1, distal enol compound 2, diol compound 3. [0003] [0004] At present, the synthesis of multi-substituted distal allyl ketone derivatives through ring-opening of ring alcohols mainly includes ring-opening fluorination of ring alcohols, alkynylation, cyanation, and amination, but direct allylation has not yet been reported. reports. Moreover, most of the existing synthesis methods use a high-temperature heating system, which consumes a lot of...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/343C07C67/48C07C67/54C07C67/56C07C69/738
CPCC07C67/343C07C67/48C07C67/54C07C67/56C07C69/738
Inventor 夏吾炯王俊雷苟宝权
Owner HARBIN INST OF TECH
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