α-tetrasubstituted chiral acetylenone compound and its preparation method and application

A compound and tetra-substitution technology, applied in the field of chiral compound synthesis, can solve the problems of harsh preparation conditions, unfavorable subsequent transformation of products, and complicated processes

Active Publication Date: 2021-08-20
PEKING UNIV SHENZHEN GRADUATE SCHOOL
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The present invention provides an α-tetrasubstituted chiral acetylenone compound and a preparation method thereof, aiming at solving the problems of harsh preparation conditions, low yield and complex process of the existing α-tetrasubstituted chiral acetylenone compound, which is unfavorable for subsequent transformation of the product. Technical problems such as limited product application range

Method used

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  • α-tetrasubstituted chiral acetylenone compound and its preparation method and application
  • α-tetrasubstituted chiral acetylenone compound and its preparation method and application
  • α-tetrasubstituted chiral acetylenone compound and its preparation method and application

Examples

Experimental program
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Effect test

Embodiment 1

[0116] This example provides a chiral R-4-fluoro-4-phenyl-1,6-bis(triisopropylsilyl)-n-hexane-1,5-diyn-3-one and its preparation method . The structural formula of the R-4-fluoro-4-phenyl-1,6-bis(triisopropylsilyl) n-hexane-1,5-diyn-3-one is shown in the following molecular structural formula I1:

[0117]

[0118] Its preparation steps are as follows:

[0119] Add homo-S-3,3'-bis(2,4,6-triisopropylphenyl)-6,6'-dinitro-binaphthyl phosphate (0.005mmol, 0.1 eq), sodium carbonate (0.10mmol, 2.0eq), 1-chloromethyl-4-fluoro-1,4-diazabicyclo[2.2.2]octane bis(tetrafluoroborate) salt (0.06mmol, 1.2 eq) and 0.5 mL of anhydrous m-xylene, replaced with argon three times, sealed the reaction test tube and stirred at room temperature for 10 min, then placed it in a -30°C cold trap. (R,trans)-3-tert-butyldiphenylsilyloxy-1-(4-phenyl-1,6-bis(triisopropylsilyl)n-hexyl-3-ene-1, A solution of 5-diyne-3-)pyrrolidine (0.05mmol, 1.00eq) in m-xylene was slowly added to the reaction system, an...

Embodiment 2

[0121] This example provides a chiral R-4-fluoro-4-(m-methylphenyl)-1,6-bis(triisopropylsilyl)-n-hexane-1,5-diyne-3- Ketones and methods for their preparation. The structural formula of the R-4-fluoro-4-(m-methylphenyl)-1,6-bis(triisopropylsilyl)-n-hexane-1,5-diyn-3-one is as follows molecular structure formula I2 Show:

[0122]

[0123] Its preparation steps are as follows:

[0124] Add homo-S-3,3'-bis(2,4,6-triisopropylphenyl)-6,6'-dinitro-binaphthyl phosphate (0.005mmol, 0.1 eq), sodium carbonate (0.10mmol, 2.0eq), 1-chloromethyl-4-fluoro-1,4-diazabicyclo[2.2.2]octane bis(tetrafluoroborate) salt (0.06mmol, 1.2 eq) and 0.5 mL of anhydrous m-xylene, replaced with argon three times, sealed the reaction test tube and stirred at room temperature for 10 min, then placed it in a -30°C cold trap. (R,trans)-3-tert-butyldiphenylsilyloxy-1-(4-m-methylphenyl-1,6-bis(triisopropylsilyl)n-hexyl-3-ene The m-xylene solution of -1,5-diyne-3-)pyrrolidine (0.05mmol, 1.00eq) was slowly ...

Embodiment 3

[0126] This example provides a chiral R-4-fluoro-4-(p-methylphenyl)-1,6-bis(triisopropylsilyl)-n-hexane-1,5-diyne-3- Ketones and methods for their preparation. The structural formula of the R-4-fluoro-4-(p-methylphenyl)-1,6-bis(triisopropylsilyl)-n-hexane-1,5-diyn-3-one is shown in molecular structural formula I3 Show:

[0127]

[0128] Its preparation steps are as follows:

[0129] Add homo-S-3,3'-bis(2,4,6-triisopropylphenyl)-6,6'-dinitro-binaphthyl phosphate (0.005mmol, 0.1 eq), sodium carbonate (0.10mmol, 2.0eq), 1-chloromethyl-4-fluoro-1,4-diazabicyclo[2.2.2]octane bis(tetrafluoroborate) salt (0.06mmol, 1.2 eq) and 0.5 mL of anhydrous m-xylene, replaced with argon three times, sealed the reaction test tube and stirred at room temperature for 10 min, then placed it in a -30°C cold trap. (R,trans)-3-tert-butyldiphenylsilyloxy-1-(4-p-methylphenyl-1,6-bis(triisopropylsilyl)n-hexyl-3-ene The m-xylene solution of -1,5-diyne-3-)pyrrolidine (0.05mmol, 1.00eq) was slowly a...

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Abstract

The invention discloses an α-tetrasubstituted chiral acetylene compound, a preparation method and application thereof. The general molecular structure formula of the α-tetrasubstituted chiral ynone compound of the present invention is described in the general formula (I) in the description. The preparation method of the α-tetrasubstituted chiral ynone compound comprises the steps of adding the diacetylene enamine compound A into a reaction system containing a functional group reagent B, a chiral phosphoric acid catalyst and an alkaline reagent for reaction. The α-tetrasubstituted chiral acetylenone compound of the present invention can obtain a large number of chiral compounds with special ring structures through simple chemical transformation, and is widely used in the preparation of pharmaceutical intermediates. Its preparation method has simple process, low requirements on reaction conditions, safe and controllable reaction process, high atom utilization rate and production efficiency, and at the same time efficiently guarantees the enantioselectivity of the product, and the introduction of the concept of asymmetric catalysis of organic small molecules makes the method The environmental pollution pressure of the school is small.

Description

technical field [0001] The invention belongs to the technical field of chiral compound synthesis, and in particular relates to an α-tetrasubstituted chiral acetylene compound, a preparation method thereof, and an application of the chiral α-tetrasubstituted chiral ketynone 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, the chiral α-tetrasubstituted chiral ynone compound is an important kind of chiral compounds. ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F7/12
Inventor 黄湧彭思宇汪兆丰陈杰安
Owner PEKING UNIV SHENZHEN GRADUATE SCHOOL
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