Alpha-tetra-substituted chiral acetyenic ketone compound, as well as preparation method and application thereof

A compound and four-substitution technology, applied in the field of chiral compound synthesis, can solve the problems of unfavorable subsequent conversion of products, limited product application range, harsh preparation conditions, etc., achieve safe and controllable reaction process, avoid heating or high pressure conditions, simplify The effect of the operation

Active Publication Date: 2019-06-28
PEKING UNIV SHENZHEN GRADUATE SCHOOL
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  • Abstract
  • Description
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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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  • Alpha-tetra-substituted chiral acetyenic ketone compound, as well as preparation method and application thereof
  • Alpha-tetra-substituted chiral acetyenic ketone compound, as well as preparation method and application thereof
  • Alpha-tetra-substituted chiral acetyenic ketone compound, as well as preparation method and application thereof

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 alpha-tetra-substituted chiral acetyenic ketone compound, as well as a preparation method and application thereof. The molecular structural general formula of the alpha- tetra-substituted chiral acetyenic ketone compound is as shown in general formula (I) in the specification. The preparation method comprises the following steps: adding a diyne enamine compound A into areaction system containing a functionalized reagent B, a chiral phosphoric acid catalyst and a base reagent to react, and the like. The alpha-tetra-substituted chiral acetyenic ketone compound can bewidely applied to preparation of medicinal intermediates since massive chiral compounds with a special ring structure are obtained by simple chemical transformation. The preparation method is simple in process and low in requirement for reaction conditions, has safe and controllable reaction process, high atom utilization and high production efficiency, can efficiently ensure the enantioselectivity of products, and has small environmental pollution pressure by introducing the concept of organic small-molecular asymmetric catalysis.

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 Applications(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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