[(1R,2R,5S,6S)-5-hydroxy-7-oxabicyclo[4.1.0]hept-3-en-2-yl] acetate | 312932-50-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: [(1R,2R,5S,6S)-5-hydroxy-7-oxabicyclo[4.1.0]hept-3-en-2-yl] acetate
• CAS: 312932-50-6
• 化学式: C₈H₁₀O₄
• 分子量: 170.165
• InChiKey: GKLPQRYBMGDNPX-FKSUSPILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  59.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(1R,2R,5S,6S)-5-hydroxy-7-oxabicyclo[4.1.0]hept-3-en-2-yl] acetate 在 咪唑 、 甲醇 、 氨 、 水 、 溶剂黄146 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 (3aR,6R,7S,7aR)-6,7-Bis-(tert-butyl-dimethyl-silanyloxy)-3a,6,7,7a-tetrahydro-3H-benzooxazol-2-one
  参考文献：
  名称：

  From cycloolefins to chiral, polyfunctionalized linear C6/C12 building blocks—biocatalysis, (−)-conduramine E

  摘要：

  1,4-Cyclohexadiene is the starting material for the expeditious synthesis of the 1S2S3S4R- and 1R2R3R4S-epoxy-cyclohexene-1,4-diol monoacetates through enzyme-catalyzed hydrolysis and transesterification, respectively. The absolute configurations are established by correlation of (-)-10 and known (+)-conduramine E. Ozonation and functional group manipulation open access to fully protected, polyfunctionalized C-6-aldehydes whose reductive coupling to C-2-symmetrical C-12 building blocks is being explored. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01395-2
• 作为产物：
  描述：

  Acetic acid (1R,2R,5S,6S)-5-acetoxy-7-oxa-bicyclo[4.1.0]hept-3-en-2-yl ester 在 SP 523 (Novozym 398) 作用下， 以 phosphate buffer 、 正己烷 为溶剂， 生成 [(1R,2R,5S,6S)-5-hydroxy-7-oxabicyclo[4.1.0]hept-3-en-2-yl] acetate 、 [(1S,2S,5R,6R)-5-hydroxy-7-oxabicyclo[4.1.0]hept-3-en-2-yl] acetate
  参考文献：
  名称：

  From cycloolefins to chiral, polyfunctionalized linear C6/C12 building blocks—biocatalysis, (−)-conduramine E

  摘要：

  1,4-Cyclohexadiene is the starting material for the expeditious synthesis of the 1S2S3S4R- and 1R2R3R4S-epoxy-cyclohexene-1,4-diol monoacetates through enzyme-catalyzed hydrolysis and transesterification, respectively. The absolute configurations are established by correlation of (-)-10 and known (+)-conduramine E. Ozonation and functional group manipulation open access to fully protected, polyfunctionalized C-6-aldehydes whose reductive coupling to C-2-symmetrical C-12 building blocks is being explored. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01395-2