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High optical activity chiral phthalide analog compound and synthesis method

A compound and phthalide technology, applied in the field of chiral phthalide compounds and synthesis, can solve problems such as long reaction time, unsatisfactory product corresponding selectivity, narrow application range of the method, etc., and achieve the effect of high optical purity

Inactive Publication Date: 2006-07-26
SHANGHAI INST OF ORGANIC CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the above work research has achieved certain results, some reactions require multi-step transformations, some require relatively expensive metal reagents, and some have a longer reaction time, the product corresponding selectivity is not ideal, and the scope of application of the method is narrow. and many more

Method used

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  • High optical activity chiral phthalide analog compound and synthesis method
  • High optical activity chiral phthalide analog compound and synthesis method
  • High optical activity chiral phthalide analog compound and synthesis method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Embodiment 1 chiral reagent preparation of

[0031] Dissolve (1S, 2R)-2-amino-1, 2-diphenylethanol [(1S, 2R)-2-amino-1, 2-diphenylethanol] (213 mg, 1 mmol) in 20 mL of acetonitrile, add 4- Dimethylaminopyridine (4-Dimethylaminopyridine) (10mg) and tert-butoxycarbonyl dicarbonate (Di-tert-butyl dicarbonate) (240mg, 1.1mmol) were stirred at room temperature for 10 minutes, concentrated and purified to obtain 201mg of a white solid, Yield 84%.

[0032] 1 HNMR (300MHz, CD 3 COCD 3 ): δ5.04(d, 1H, J=8.1Hz), 6.02(d, 1H, J=8.4Hz), 7.03-7.16(m, 10H), 7.25(br, 1H)ppm

Embodiment 2

[0033] Embodiment 2 chiral reagent preparation of

[0034]Dissolve (1R, 2S)-2-amino-1, 2-diphenylethanol [(1R, 2S)-2-amino-1, 2-diphenylethanol] (213 mg, 1 mmol) in 20 mL of acetonitrile, add 4- Dimethylaminopyridine (4-Dimethylaminopyridine) (10mg) and tert-butoxycarbonyl dicarbonate (Di-tert-butyl dicarbonate) (240mg, 1.1mmol) were stirred at room temperature for 10 minutes, concentrated and purified to obtain 210mg of a white solid, Yield 88%.

[0035] 1 HNMR (300MHz, CD 3 COCD 3 ): δ5.06(d, 1H, J=8.1Hz), 6.03(d, 1H, J=8.4Hz), 7.04-7.17(m, 10H), 7.27(br, 1H)ppm

Embodiment 3

[0036] Embodiment 3 chiral reagent preparation of

[0037] The operation method is the same as Example 1, the reaction raw material is (1S, 2R)-2-amino-1,2-bis(p-methylphenyl)ethanol, and the yield is 80%

[0038] 1 HNMR (300MHz, CD 3 COCD 3 ): δ1.96(s, 3H), 2.72(s, 3H), 4.98(dd, 1H, J1=7.8Hz, J2=7.2Hz), 5.24(d, 1H, J=8.1Hz), 6.15(d , 1H, J=7.5Hz), 7.08-7.26(m, 8H)ppm

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Abstract

The invention relates to a chirality phthalide compound and its synthesizing process, wherein the compound has a structure disclosed in the specification, wherein R1 is aryl or O- or S-containing 2-7 heteroaryl, the aryl can be phenyl, naphthyl, halogeno benzene, C1-C6 alkoxy substituted phenyl, C1-C8 alkyl substituted phenyl, R2, R3, R4 or R5 is H, halogen, C1-C8 alkyl or C1-C6 alkoxy, or the adjacent R2, R3, R4 or R5 substituent is -C4H4-, * represents chirality, wherein when R2, R3, R4 and R5 are all H, R1 is not phenyl. The compound can be prepared through asymmetric method.

Description

technical field [0001] The invention relates to a series of chiral phthalide compounds with high optical purity and a synthesis method. Background technique [0002] Phthalide is a class of lactone compounds that widely exist in nature, especially in plants, and many of them have physiological activity. In the early reports, to obtain optically pure phthalides, the commonly used method is to open the lactone ring to obtain an acid, then split it with a chiral reagent, and then close the ring to form a lactone. Afterwards, there have been some reports on methods for obtaining chiral phthalides by asymmetric synthesis. For example, in 1983, M.A.Hanagan and L.M.Trefonas reported the use of chiral oxazoline as a prosthetic group to asymmetrically synthesize chiral phthalide (M.A.Hanagan, etc. Tetrahedron 1983, 39, 1911), and then other groups reported Asymmetric synthesis of chiral phthalides controlled by chiral prosthetic groups. In 1996, H.C. Brown reported the asymmetric ...

Claims

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Application Information

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IPC IPC(8): C07D307/88C07D409/04
Inventor 徐明华林国强黄凌琳
Owner SHANGHAI INST OF ORGANIC CHEMISTRY - CHINESE ACAD OF SCI
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