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Quaternary phosphonium salt compound and preparation method thereof

A technology for quaternary phosphonium salts and compounds, which is applied in the field of quaternary phosphonium salt compounds and their preparation, can solve the problems of unreported, large amount of catalyst, slow reaction speed, etc., to improve catalytic activity and reaction stereoselectivity, and improve reaction active effect

Inactive Publication Date: 2015-08-19
KUNMING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This type of catalyst has the characteristics of dual functions, which can achieve better stereo control and better catalytic activity in the corresponding asymmetric catalytic reaction, so as to overcome the relatively large amount of catalyst and slow reaction speed in some small molecule catalytic reactions. and other shortcomings
[0004] The molecular structure and preparation method of this quaternary phosphonium salt catalyst have not yet been reported.

Method used

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  • Quaternary phosphonium salt compound and preparation method thereof
  • Quaternary phosphonium salt compound and preparation method thereof
  • Quaternary phosphonium salt compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Embodiment 1: structural formula is the quaternary phosphonium salt compound shown in formula I:

[0035] where: R 1 is methyl;

[0036] The synthetic route of above-mentioned compound is as follows:

[0037]

[0038](1) Add 28.5 g (190.5 mmol) L-tartaric acid into a 250 mL three-necked bottle at room temperature, then add 90 mL of methanol, stir at room temperature until the tartaric acid is completely dissolved, transfer it to an ice bath, and slowly add 55.3 mL (762 mmol) thionyl chloride, after 30 min, remove the ice bath, reflux reaction in an oil bath at 80°C for 9 h, pour the reactant into 120 mL of cold saturated sodium bicarbonate solution and vigorously stir for 30 min, separate The organic phase and the aqueous phase were extracted 3 times with ethyl acetate, the organic phases were combined, and dried over anhydrous magnesium sulfate to obtain 33.2 g of the product L-dimethyl tartrate, with a yield of 98%;

[0039] (2) Take 24 g of L-dimethyl tart...

Embodiment 2

[0048] Embodiment 2: structural formula is the quaternary phosphonium salt compound shown in formula I:

[0049] where: R 1 is phenyl;

[0050] R 1 Group is the synthetic route of the chiral quaternary phosphonium salt catalyst 1b of phenyl as follows:

[0051]

[0052] (1) At room temperature, put 28.5 g (190.0 mmol) of L-tartaric acid into a 250 mL three-neck bottle, then add 100 mL of methanol, stir at room temperature until the tartaric acid is completely dissolved, then transfer it to an ice bath, and slowly add 55.3 mL ( 762 mmol) thionyl chloride, continue to stir for 30 min, remove the ice bath, and reflux on the oil bath for 9 h; pour the reactant into 120 mL of cold sodium bicarbonate solution and stir vigorously for 30 min, then wash with acetic acid Extracted with ethyl ester and dried over anhydrous magnesium sulfate to obtain 33.14 g of the product L-dimethyl tartrate with a yield of 98%.

[0053] (2) Take 16 g (89.89 mmol) of L-dimethyl tartrate obtaine...

Embodiment 3

[0058] Embodiment 3: structural formula is the quaternary phosphonium salt compound shown in formula I:

[0059] where: R 1is n-butyl;

[0060] R 1 Group is the synthetic route of the chiral quaternary phosphonium salt catalyst 1c of n-butyl as follows:

[0061]

[0062] (1) At room temperature, put 28.5 g (190.0 mmol) of L-tartaric acid into a 250 mL three-necked bottle, then add 100 mL of methanol, stir at room temperature until the tartaric acid is completely dissolved, transfer it to an ice bath, and slowly add 68.9 mL ( 950 mmol) of thionyl chloride, continued to stir for 30 min, removed the ice bath, and refluxed on the oil bath for 9 h. The reactant was poured into 120 mL of cold sodium bicarbonate solution and vigorously stirred for 30 min, then extracted with ethyl acetate and dried over anhydrous magnesium sulfate to obtain 33.1 g of the product L-dimethyl tartrate with a yield of 98%.

[0063] (2) Take 21.72 g (122 mmol) of L-dimethyl tartrate obtained in ...

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Abstract

The present invention discloses a quaternary phosphonium salt compound and a preparation method thereof. The method uses cheap and readily available L-tartaric acid as the raw material, and conducts carboxyl esterification, hydroxyl protection, Grignard reaction, azide substitution, azide reduction and final reaction with phosphorus pentachloride, so as to obtain the quaternary phosphonium salt compound. The quaternary phosphonium salt compound is a novel Bronsted acid catalyst (a hydrogen bond donor catalyst), and can be used in the catalysis of asymmetric Mannich reaction, Michael reaction and Henry reaction.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and relates to a quaternary phosphonium salt compound prepared by using L-tartaric acid as a raw material and a preparation method thereof. Background technique [0002] Organic small molecule catalysis has been developed very rapidly in the past three decades. Because organic small molecule catalysts usually have rich sources of raw materials and are relatively cheap and easy to obtain, their synthesis is relatively simple, their properties are relatively stable, their reaction conditions are mild, and they are easy to operate. Compared with metal catalysts, the final products of their catalytic reactions will not cause heavy metal pollution. Therefore, It is especially suitable for the fields of pharmaceuticals, fine chemicals and pesticides, and has good industrial application prospects. In the frontier field of organic small molecule catalysis, chiral Bronsted acid catalysts (hydrogen bond d...

Claims

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Application Information

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IPC IPC(8): C07F9/6584B01J31/02C07B53/00C07C201/12C07C205/16
Inventor 廖霞俐高凯任玉峰杨波杨健
Owner KUNMING UNIV OF SCI & TECH
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