(2S,3S,5S)-3-<(tert-butyldimethylsilyl)oxy>-2-hexyl-5-undecylcyclopentan-1-one | 134360-65-9

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (2S,3S,5S)-3-<(tert-butyldimethylsilyl)oxy>-2-hexyl-5-undecylcyclopentan-1-one
• 英文别名: (2S,3S,5S)-3-[tert-butyl(dimethyl)silyl]oxy-2-hexyl-5-undecylcyclopentan-1-one
• CAS: 134360-65-9
• 化学式: C₂₈H₅₆O₂Si
• 分子量: 452.837
• InChiKey: AMUVGKBEOSNRLV-GSDHBNRESA-N

物化性质

• 沸点：
  492.4±38.0 °C(Predicted)
• 密度：
  0.88±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.47
• 重原子数：
  31
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S,3S,5S)-3-<(tert-butyldimethylsilyl)oxy>-2-hexyl-5-undecylcyclopentan-1-one 在 氢氟酸 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以71%的产率得到(2S,3S,5S)-3-hydroxy-2-hexyl-5-undecylcyclopentan-1-one
  参考文献：
  名称：

  Synthesis of tetrahydrolipstatin

  摘要：

  An asymmetric synthesis of tetrahydrolipstatin (4) is described. Application of our previously described in situ cyclopentadiene alkylation-asymmetric hydroboration protocol provided the key chiral alcohol 9. In the course of this work, the presence of a free hydroxyl group was found to exert a strong directing effect on the regioselectivity of a Baeyer-Villiger reaction (16 --> 17). Subsequent transformations of lactone 17 produced tetrahydrolipstatin (4).

  DOI：

  10.1021/jo00015a027
• 作为产物：
  描述：

  1-溴十一烷 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 反应 0.83h， 生成 (2S,3S,5S)-3-<(tert-butyldimethylsilyl)oxy>-2-hexyl-5-undecylcyclopentan-1-one
  参考文献：
  名称：

  Synthesis of tetrahydrolipstatin

  摘要：

  An asymmetric synthesis of tetrahydrolipstatin (4) is described. Application of our previously described in situ cyclopentadiene alkylation-asymmetric hydroboration protocol provided the key chiral alcohol 9. In the course of this work, the presence of a free hydroxyl group was found to exert a strong directing effect on the regioselectivity of a Baeyer-Villiger reaction (16 --> 17). Subsequent transformations of lactone 17 produced tetrahydrolipstatin (4).

  DOI：

  10.1021/jo00015a027

文献信息

• CHADHA, N. K.;BATCHO, A. D.;TANG, P. C.;COURTNEY, L. F.;COOK, C. M.;WOVKU+, J. ORG. CHEM., 56,(1991) N5, C. 4714-4718
  作者：CHADHA, N. K.、BATCHO, A. D.、TANG, P. C.、COURTNEY, L. F.、COOK, C. M.、WOVKU+

  DOI：——

  日期：——
• Synthesis of tetrahydrolipstatin
  作者：N. K. Chadha、A. D. Batcho、P. C. Tang、L. F. Courtney、C. M. Cook、P. M. Wovkulich、Milan R. Uskokovic

  DOI：10.1021/jo00015a027

  日期：1991.7

  An asymmetric synthesis of tetrahydrolipstatin (4) is described. Application of our previously described in situ cyclopentadiene alkylation-asymmetric hydroboration protocol provided the key chiral alcohol 9. In the course of this work, the presence of a free hydroxyl group was found to exert a strong directing effect on the regioselectivity of a Baeyer-Villiger reaction (16 --> 17). Subsequent transformations of lactone 17 produced tetrahydrolipstatin (4).