(5R,6S,9S)-9-[(tert-butyldimethylsiloxy)methyl]-6-methyl-1-oxa-2-oxospiro[4.4]nonane | 190246-86-7

• 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: (5R,6S,9S)-9-[(tert-butyldimethylsiloxy)methyl]-6-methyl-1-oxa-2-oxospiro[4.4]nonane
• 英文别名: (5R,6S,9S)-9-[[tert-butyl(dimethyl)silyl]oxymethyl]-6-methyl-1-oxaspiro[4.4]nonan-2-one
• CAS: 190246-86-7
• 化学式: C₁₆H₃₀O₃Si
• 分子量: 298.498
• InChiKey: YCUCISPDBWVVKL-HEHGZKQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.13
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5R,6S,9S)-9-[(tert-butyldimethylsiloxy)methyl]-6-methyl-1-oxa-2-oxospiro[4.4]nonane 在 platinum(IV) oxide 4-二甲氨基吡啶 、 四丁基氟化铵 、 氧气 、 三乙基硼氢化锂 作用下， 以 四氢呋喃 、 吡啶 、 乙醚 为溶剂， 反应 17.0h， 生成 (1R,2S,5S)-2-(2-hydroxyisopropyl)-1-(3-hydroxypropyl)-5-methylcyclopentanol
  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：

  (5S,6R,9S)-6-(acetoxymethyl)-9-(hydroxymethyl)-1-oxa-2-oxospiro[4.4]nonane 在 咪唑 、 碘 、 potassium carbonate 、 三苯基膦 、 锌 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.83h， 生成 (5R,6S,9S)-9-[(tert-butyldimethylsiloxy)methyl]-6-methyl-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.