Unlock instant, AI-driven research and patent intelligence for your innovation.

A method for synthesizing 1,2-dimethylene cyclobutane chiral compound

A technology for dimethylene cyclobutane and chiral compounds, which is applied in the field of synthesizing 1,2-dimethylene cyclobutane chiral compounds, and can solve the problems that chiral cyclobutane has not been reported.

Active Publication Date: 2019-09-20
FUJIAN INST OF RES ON THE STRUCTURE OF MATTER CHINESE ACAD OF SCI
View PDF1 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, the method for preparing chiral cyclobutane by rhodium-catalyzed allenamine [2+2] cycloaddition has not yet been reported

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • A method for synthesizing 1,2-dimethylene cyclobutane chiral compound
  • A method for synthesizing 1,2-dimethylene cyclobutane chiral compound
  • A method for synthesizing 1,2-dimethylene cyclobutane chiral compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0098] The preparation of embodiment 1 product 1

[0099] Product 1 : R in formula II-1 and formula II-2 1 and R 2 They are benzyl and p-toluenesulfonyl (abbreviated as TS); the product corresponding to formula II-1 is marked as product 1-1, and the product corresponding to formula II-1 is marked as product 1-2.

[0100] The Chinese name of product 1-1 is: N,N'-((1S,2S)-3,4-dimethylenecyclobutane-1,2-substituted)bis(N-benzyl-4-p-methyl phenylsulfonyl);

[0101] The English name of Product 1-1 is:

[0102] N,N'-((1S,2S)-3,4-dimethylenecyclobutane-1,2-diyl)bis(N-benzyl-4-methy lbenzenesulfonamide)

[0103] The structural formulas of products 1-1 and 1-2 are respectively:

[0104]

[0105] The allene amine raw material that adopts is: R in the formula I 1 and R 2 Allenamines of benzyl and p-toluenesulfonyl, respectively. Concrete preparation process is as follows:

[0106] In the dry reaction tube, add rhodium source, ligand, allenamine, and organic solvent in sequen...

Embodiment 2

[0122] The preparation of embodiment 2 product 2

[0123] Product 2 : R in formula II-1 and formula II-2 1 and R 2 They are benzyl and methylsulfonyl (abbreviated as MS); the product corresponding to formula II-1 is marked as product 2-1, and the product corresponding to formula II-1 is marked as product 2-2.

[0124]The Chinese name of product 2-1 is: N,N'-((1S,2S)-3,4-dimethylenecyclobutane-1,2-substituted)bis(N-benzyl-4-methyl Sulfonyl)

[0125] The English name of Product 2-1 is:

[0126] N,N'-((1S,2S)-3,4-dimethylenecyclobutane-1,2-diyl)bis(N-benzylmethanesulfonamide)

[0127] The structural formulas of products 2-1 and 2-2 are respectively:

[0128]

[0129] The specific preparation process is as the preparation of sample 1#-1 in Example 1, except that the achiral and chiral ligands used are compounds shown in formula (3) (n=1, R 12 = phenyl) and compound (R) shown in formula (7) 17 and R 18 Both are phenyl); the allenamine raw material adopted is: R in form...

Embodiment 3

[0140] The preparation of embodiment 3 product 3

[0141] Product 3 : R in formula II-1 and formula II-2 1 and R 2 They are respectively 4-methoxybenzyl and p-toluenesulfonyl (abbreviated as TS); the product corresponding to formula II-1 is marked as product 3-1, and the product corresponding to formula II-1 is marked as product 3-2.

[0142] The Chinese name of product 3-1 is: N,N'-((1S,2S)-3,4-dimethylenecyclobutane-1,2-substituted)bis(N-(4-methoxybenzyl base)-4-p-toluenesulfonyl)

[0143] The English name of Product 3-1 is:

[0144] N,N'-((1S,2S)-3,4-dimethylenecyclobutane-1,2-diyl)bis(N-(4-methoxybenzyl)-4-methylbenzonesulfonamide)

[0145] The structural formulas of product 3-1 and product 3-2 are respectively:

[0146]

[0147] The specific preparation process is as the preparation of sample 1#-1 in Example 1, except that the achiral and chiral ligands used are compounds shown in formula (3) (n=1, R 12 = phenyl) and compound (R) shown in formula (7) 17 and R ...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

PropertyMeasurementUnit
melting pointaaaaaaaaaa
melting pointaaaaaaaaaa
melting pointaaaaaaaaaa
Login to View More

Abstract

Disclosed in the present application is a method for synthesizing a 1,2-dimethylene cyclobutane chiral compound. The 1,2-dimethylene cyclobutane chiral compound is synthesized from an allenylamine compound in the presence of a rhodium complex. The 1,2-dimethylene cyclobutane chiral compound can be synthesized at a high efficiency, a high enantioselectivity and a high stereoselectivity under mild reaction conditions in the method.

Description

technical field [0001] The application relates to a method for synthesizing 1,2-dimethylene cyclobutane chiral compound, which belongs to the field of natural products and medicines. Background technique [0002] Cyclobutane-derived compounds play an important role in many natural products and drug molecules. The current method for synthesizing cyclobutane is mainly to synthesize cyclobutane through [2+2] cycloaddition of alkenes, alkynes, allenes and other unsaturated systems. In recent years, a lot of research has been carried out on the method of [2+2] cycloaddition of alkenes or allenes to other unsaturated systems to synthesize cyclobutane by heating, but this kind of reaction has poor selectivity and high reaction temperature. (Usually greater than 200°C), long reaction time (usually greater than 72h) disadvantages. [0003] With the progress of [2+2] cycloaddition synthesis of cyclobutane in the field of photocatalysis, the methods of metal-catalyzed [2+2] cycloaddi...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07B53/00C07C209/68C07C211/40C07C303/40C07C311/20C07D209/14C07D307/14C07D317/58C07D333/20C07F7/18
Inventor 康强郑伟锋
Owner FUJIAN INST OF RES ON THE STRUCTURE OF MATTER CHINESE ACAD OF SCI