cis-2,2-(ethylenedioxy)cyclopentane-1,3-dimethanol diacetate | 190246-72-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cis-2,2-(ethylenedioxy)cyclopentane-1,3-dimethanol diacetate
• 英文别名: [(6S,9R)-9-(acetyloxymethyl)-1,4-dioxaspiro[4.4]nonan-6-yl]methyl acetate
• CAS: 190246-72-1
• 化学式: C₁₃H₂₀O₆
• 分子量: 272.298
• InChiKey: CEQSASSOONLSHV-TXEJJXNPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  cis-2,2-(ethylenedioxy)cyclopentane-1,3-dimethanol diacetate 在 phosphate buffer 作用下， 以 丙酮 为溶剂， 反应 16.0h， 以91%的产率得到(1S,3R)-1-(acetoxymethyl)-2,2-(ethylenedioxy)-3-(hydroxymethyl)cyclopentane
  参考文献：
  名称：

  Enantioselective Synthesis of (−)-Curcumanolide A Using Enzymatic Transesterification of meso-Spirodiol

  摘要：

  meso-Spirodiol 12 and spirodiacetate 13 were stereoselectively prepared using pi-face selective Grignard addition to norbornanone 7. Asymmetric transesterification of meso-diol and hydrolysis of meso-diacetate were studied using lipases. Pseudomonas fluorescens lipase-catalyzed transesterification of meso-diol 12 afforded the monoacetate (-)-21 of high enantiomeric excess (>99% ee). The formal synthesis of(-)-curcumanolide A has been achieved from the optically active (-)-21.

  DOI：

  10.1021/jo962150r
• 作为产物：
  描述：

  乙酸酐 、 螺[1,3-二氧戊环-2,7'-双环[2.2.1]庚-2-烯] 在 sodium tetrahydroborate 、 臭氧 作用下， 生成 cis-2,2-(ethylenedioxy)cyclopentane-1,3-dimethanol diacetate
  参考文献：
  名称：

  Enantioselective Synthesis of (−)-Curcumanolide A Using Enzymatic Transesterification of meso-Spirodiol

  摘要：

  meso-Spirodiol 12 and spirodiacetate 13 were stereoselectively prepared using pi-face selective Grignard addition to norbornanone 7. Asymmetric transesterification of meso-diol and hydrolysis of meso-diacetate were studied using lipases. Pseudomonas fluorescens lipase-catalyzed transesterification of meso-diol 12 afforded the monoacetate (-)-21 of high enantiomeric excess (>99% ee). The formal synthesis of(-)-curcumanolide A has been achieved from the optically active (-)-21.

  DOI：

  10.1021/jo962150r

文献信息

• Enantioselective Synthesis of (−)-Curcumanolide A Using Enzymatic Transesterification of <i>meso</i>-Spirodiol
  作者：Toshiaki Fujita、Masakazu Tanaka、Yoshihiko Norimine、Hiroshi Suemune、Kiyoshi Sakai

  DOI：10.1021/jo962150r

  日期：1997.6.13

  meso-Spirodiol 12 and spirodiacetate 13 were stereoselectively prepared using pi-face selective Grignard addition to norbornanone 7. Asymmetric transesterification of meso-diol and hydrolysis of meso-diacetate were studied using lipases. Pseudomonas fluorescens lipase-catalyzed transesterification of meso-diol 12 afforded the monoacetate (-)-21 of high enantiomeric excess (>99% ee). The formal synthesis of(-)-curcumanolide A has been achieved from the optically active (-)-21.