Chiral 1,2-diamine compound and preparation method and application thereof

A compound and diamine technology, applied in the field of organic compound synthesis, can solve the problems of limited application range of 1,2-diamine compounds, harsh preparation conditions, complicated processes, etc., and meet the requirements of safe and controllable reaction process and reaction conditions. Low, simple process effect

Active Publication Date: 2016-03-02
PEKING UNIV SHENZHEN GRADUATE SCHOOL
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The purpose of the present invention is to overcome the above-mentioned deficiencies of the prior art, and provide a kind of chiral 1,2-diamine compound and its preparation method and appl

Method used

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  • Chiral 1,2-diamine compound and preparation method and application thereof
  • Chiral 1,2-diamine compound and preparation method and application thereof
  • Chiral 1,2-diamine compound and preparation method and application thereof

Examples

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preparation example Construction

[0074] On the other hand, on the basis of the above-mentioned chiral 1,2-diamine compound of the present invention, the embodiment of the present invention also provides the chiral 1,2-diamine compound of the above molecular structure general formula (I). A preparation method of amine compound. The method comprises the steps of:

[0075] S01: respectively provide the fatty chain amine compound A and the nitroalkene compound B represented by the following structural formula:

[0076]

[0077] S02: adding the aliphatic chain amine compound A and the nitroalkene compound B into a reaction system containing an azacarbene catalyst, a proton additive, an alkali reagent and a water-absorbing additive to react at a temperature of -80-25°C to obtain The following structural general formula is a chiral 1,2-diamine compound shown in (I),

[0078]

[0079] Specifically, in the above step S01, R in the molecular structural formula of fatty chain amine compound A 1 , R 2 The repre...

Embodiment 1

[0100] This example provides (R)-N-benzyl-3,3,3-trifluoro-2-phenylpropyl-1,2-diamine and its preparation method. The structural formula of the (R)-N-benzyl-3,3,3-trifluoro-2-phenylpropyl-1,2-diamine is shown in the following molecular structural formula I1:

[0101]

[0102] Its preparation steps are as follows:

[0103] In a dry 10 mL test tube, add mesitylene-substituted indenol-derived triazole carbene catalyst (0.01 mmol, 0.2 eq), 100 mg of pre-activated powdered molecular sieves and 0.4 mL of anhydrous toluene, replace with argon three times, and add 0.01 mmol of LiHMDS , replaced with argon three times again, added 2.2uL hexafluoroisopropanol (0.02mmol, 0.4eq), sealed the reaction tube and stirred at room temperature for 0.5h. β-trifluoromethyl substituted nitrostyrene (0.05mmol, 1.0eq) was dissolved in 0.2mL toluene and slowly added to the reaction system, and stirred at -78°C for 0.5 hours. Aliphatic chain amine reagent (0.1mmol, 2.0eq) was dissolved in 0.6mL and ...

Embodiment 2

[0105] Embodiment 2 (chiral diamine precursor-nitro compound)

[0106] This example provides a kind of (R)-1,1,1-trifluoro-N-(2-methylphenyl)-3-nitro-2-phenylpropyl-2-amine and its preparation method . The structural formula of the (R)-1,1,1-trifluoro-N-(2-methylbenzyl)-3-nitro-2-phenylpropyl-2-amine is shown in the following molecular structural formula I2:

[0107]

[0108] Its preparation method refers to the preparation method of (R)-N-benzyl-1,1,1-trifluoro-3-nitro-2-phenylpropyl-2-amine in Example 1, the difference is that 2 - Methylbenzylamine (0.1 mmol) instead of benzylamine. The reaction solution was filtered through a glass dropper containing silica gel, rinsed with ether, the filtrate was spin-dried, and separated by column chromatography to obtain the target product precursor, a colorless oily liquid, with a yield of 67% and an ee value of 91%.

[0109] The product I2 prepared is subjected to characterization data analysis, and the result is: 1 HNMR (400MHz...

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Abstract

The invention discloses a chiral 1,2-diamine compound and a preparation method and application thereof. The molecular structure general formula of the chiral 1,2-diamine compound is shown as the general formula (I) in the specification. The preparation method of the chiral 1,2-diamine compound comprises the steps that an amine compound A and a nitroolefin compound B are added to a reaction system containing an n-heterocyclic carbine catalyst, an alkali reagent, a proton additive and a dewatering reagent for reacting and other steps. The chiral 1,2-diamine compound comprises chiral quaternary carbon atoms containing electrondrawing groups and amino groups, and can be widely used for synthesizing drug intermediates, especially heterocyclic ring structure compounds, and preparing functional materials. The preparation method is simple in process and low in requirement for reaction conditions, the reaction process is safe and controllable, the atom utilization rate and production efficiency are high, meanwhile, the enantioselectivity of products is efficiently guaranteed, and the environment pollution pressure of the methodology is low through the introduction of the small organic molecule asymmetric catalysis concept.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, and in particular relates to a chiral 1,2-diamine compound, its preparation method and the application of the chiral 1,2-diamine compound. Background technique [0002] Chiral compounds refer to the same molecular weight and molecular structure, but the left and right arrangements are opposite, such as the enantiomer of the real object and its mirror. Human left and right hands have the same structure, and the order from thumb to little finger is the same, but the order is different. The left hand is from left to right, and the right hand is from right to left, so it is called "chirality". That is, a pair of molecules. Because they cannot overlap each other like two human hands, they are also called chiral compounds. [0003] Among them, chiral 1,2-diamine compounds are an important kind of chiral compounds. Chiral 1,2-diamine compounds are an important class of building blo...

Claims

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Application Information

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IPC IPC(8): C07C209/60C07C209/34C07C211/27C07C211/29C07C213/08C07C217/58C07C211/35C07C217/08C07D333/20C07D213/36B01J31/02
CPCB01J31/0232B01J31/0244B01J2231/321C07B53/00C07B2200/07C07C209/325C07C209/60C07C213/08C07D213/36C07D333/20C07C211/27C07C211/29C07C217/58C07C211/35C07C217/08
Inventor 陈杰安黄湧
Owner PEKING UNIV SHENZHEN GRADUATE SCHOOL
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