Acetic acid (1R,2R,5R,6R)-2,6-diacetoxy-5-hydroxy-cyclohex-3-enyl ester | 191793-10-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Acetic acid (1R,2R,5R,6R)-2,6-diacetoxy-5-hydroxy-cyclohex-3-enyl ester
• 英文别名: [(1R,4R,5R,6R)-5,6-diacetyloxy-4-hydroxycyclohex-2-en-1-yl] acetate
• CAS: 191793-10-9
• 化学式: C₁₂H₁₆O₇
• 分子量: 272.255
• InChiKey: CUOUFPIIDGEYPC-DDHJBXDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  99.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Acetic acid (1R,2R,5R,6R)-2,6-diacetoxy-5-hydroxy-cyclohex-3-enyl ester 在 ammonium hydroxide 作用下， 生成 (-)-conduritol E
  参考文献：
  名称：

  An efficient enzymatic preparation of (+)- and (−)-conduritol E, a cyclitol with C2 symmetry

  摘要：

  Lypozyme(R) IM (immobilised lipase from Mucor miehei) catalyses the enantiomeric alcoholysis of tetraacetylconduritol E (+/-)-2 to give enantiopure (1R,2R,3R,4R)-tetrahydroxycyclohex-5-ene (-)-1, and the unreacted ester (1S,2S,3S,4S)-tetraacetyloxycyclohex-5-ene, (+)-2. The latter was transformed by basic hydrolysis into (+)-1 in high yield and 95% ee. Selective amination of partial ester (-)-3, obtained by short alcoholysis of (+/-)-2, furnished the previously unreported conduramine F-4, (-)-4. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00129-8
• 作为产物：
  描述：

  cis-1,2-dihydrocatechol 在 吡啶 、 四氧化锇 、 Lipozyme IM 、 N-甲基吗啉氧化物 、 正丁醇 作用下， 以 二氯甲烷 为溶剂， 反应 29.0h， 生成 Acetic acid (1R,2R,5R,6R)-2,6-diacetoxy-5-hydroxy-cyclohex-3-enyl ester
  参考文献：
  名称：

  An efficient enzymatic preparation of (+)- and (−)-conduritol E, a cyclitol with C2 symmetry

  摘要：

  Lypozyme(R) IM (immobilised lipase from Mucor miehei) catalyses the enantiomeric alcoholysis of tetraacetylconduritol E (+/-)-2 to give enantiopure (1R,2R,3R,4R)-tetrahydroxycyclohex-5-ene (-)-1, and the unreacted ester (1S,2S,3S,4S)-tetraacetyloxycyclohex-5-ene, (+)-2. The latter was transformed by basic hydrolysis into (+)-1 in high yield and 95% ee. Selective amination of partial ester (-)-3, obtained by short alcoholysis of (+/-)-2, furnished the previously unreported conduramine F-4, (-)-4. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00129-8