(5S,6R,9S)-6,9-bis(hydroxymethyl)-1-oxa-2-oxospiro[4.4]nonane | 190246-75-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (5S,6R,9S)-6,9-bis(hydroxymethyl)-1-oxa-2-oxospiro[4.4]nonane
• CAS: 190246-75-4
• 化学式: C₁₀H₁₆O₄
• 分子量: 200.235
• InChiKey: NVRLUMMQBCWNQP-DIYOJNKTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.07
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  66.76
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (5S,6R,9S)-6,9-bis(hydroxymethyl)-1-oxa-2-oxospiro[4.4]nonane 在 4-二甲氨基吡啶 、 phosphate buffer 作用下， 以 吡啶 、 丙酮 为溶剂， 反应 214.0h， 生成 (5S,6R,9S)-6-(acetoxymethyl)-9-(hydroxymethyl)-1-oxa-2-oxospiro[4.4]nonane
  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：

  ani-2'-oxa-3'-oxospiro[bicyclo[2.2.1]hept-2-ene-7,1'-cyclopentane] 在 sodium tetrahydroborate 、 臭氧 作用下， 生成 (5S,6R,9S)-6,9-bis(hydroxymethyl)-1-oxa-2-oxospiro[4.4]nonane
  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.