Method for preparing chiral alkynyl tertiary alcohol

An alkynyl tertiary alcohol and chirality technology is applied in the field of preparing chiral alkynyl tertiary alcohol, which can solve the problems of inability to large-scale application, low yield, and no natural chirality of abscisic folic acid.

Inactive Publication Date: 2014-01-15
方茂海
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] However, this method of J.R. Hanson and C. Uyanik does not propose a measure to control the chirality of the natural abscisic acid finally obtained
The chemical synthesis of natural chiral abscisic acid is still subject to expensive chiral auxiliary reagents, low yield and difficult to scale up, so it cannot be applied on a large scale

Method used

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  • Method for preparing chiral alkynyl tertiary alcohol
  • Method for preparing chiral alkynyl tertiary alcohol
  • Method for preparing chiral alkynyl tertiary alcohol

Examples

Experimental program
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Effect test

Embodiment Construction

[0023] 1. Synthesis of racemic 4-hydroxy-2-ynyl acid 4:

[0024] Compound 1 can be prepared from 4-oxoisophorone (4-oxoisophorone) according to literature methods, see J.R.Hanson and C.Uyanik, J.Chem.Res., 2003, 7, 426-427. Under nitrogen, 80 mL of dry THF and ethyl propiolate (4.91 g, 50 mmol) were added to a dry 500 mL round bottom flask and magnetic stirring was started. The round bottom flask was immersed in a dry ice acetone bath and cooled until the temperature of the solution in the flask was below -60°C. Lithium diisopropylamide solution (25 mL, 50 mmol, 2 mol / L solution) was slowly added dropwise to the solution in the flask, keeping the internal temperature not exceeding -60 °C. After the dropwise addition, continue to keep stirring at -60°C for one hour.

[0025] Under nitrogen protection, compound 1 (3.92 g, 20 mmol) was dissolved in 20 mL of dry THF, and then slowly added dropwise to the above solution, keeping the temperature not exceeding -60 °C. After the dr...

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Abstract

The invention relates to a preparation method of chiral alkynyl tertiary alcohol and use thereof. The method comprises the following steps: mixing racemic hydroxy acetylenic acid and a solvent isopropyl alcohol with chiral pure S-(-)-methylbenzylamine or R-(+)-methylbenzylamine to split out chiral hydroxy acetylenic acid, and adding the chiral hydroxy acetylenic acid and a cuprous chloride catalyst into an acetonitrile solution to react to obtain the chiral alkynyl tertiary alcohol. The chiral alkynyl tertiary alcohol can not only be used for preparing natural chiral abscisic acid and enantiomers thereof, but also used for synthesizing chiral abscisic acid analogues. The method is low in cost, good in splitting effect and capable of being used in a large scale to overcome the defects of an existing chemical synthesis method of abscisic acid of expensive chiral auxiliary reagent, low yield and difficulty in realizing mass production.

Description

technical field [0001] The invention relates to an organic chemical method which can be used for the chemical synthesis and chiral resolution of the important intermediate of abscisic folic acid, especially the method for the preparation and resolution of the chiral alkynyl tertiary alcohol. Background technique [0002] Abscisic acid (Abscisic acid, also known as S-inducer) and auxins (Auxins), gibberellins (Giberellins), cytokinins (Cytokinins) and ethylene (Ethylene) are called the five major plant growth hormones (phytohormone), Or also called plant growth regulator (plant growth regulator). Natural abscisic acid is a single small organic molecule with optical activity (S-(+)-chiral isomer, error! Reference source not found.). Abscisic acid has been extensively focused and researched since it was discovered in the 1960s. In almost all higher plants, abscisic acid has physiological functions such as regulating drought resistance, saline-alkali resistance, stress resista...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/42C07C59/90C07C49/743C07C45/65
CPCC07C51/487C07C45/676C07C51/00C07C59/90C07C49/743
Inventor 方茂海
Owner 方茂海
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