ethyl (E,4S,11R)-11-[1-(tert-butyl)-1,1-dimethylsilyl]oxy-4-hydroxy-2-dodecenoate | 142729-33-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (E,4S,11R)-11-[1-(tert-butyl)-1,1-dimethylsilyl]oxy-4-hydroxy-2-dodecenoate
• 英文别名: ethyl (E,4S,11R)-11-[tert-butyl(dimethyl)silyl]oxy-4-hydroxydodec-2-enoate
• CAS: 142729-33-7
• 化学式: C₂₀H₄₀O₄Si
• 分子量: 372.621
• InChiKey: OWBWJXFOBYYLAC-XZIRQGAESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.22
• 重原子数：
  25
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (E,4S,11R)-11-[1-(tert-butyl)-1,1-dimethylsilyl]oxy-4-hydroxy-2-dodecenoate 、 氯甲基甲基醚 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以83%的产率得到ethyl (E,4S,11R)-11-[1-(tert-butyl)-1,1-dimethylsilyl]oxy-4-(methoxymethoxy)-2-dodecenoate
  参考文献：
  名称：

  Enantioselective synthesis of (+)-patulolide C via proline-catalyzed sequential α-aminooxylation and Horner–Wadsworth–Emmons olefination

  摘要：

  The enantioselective total synthesis of (+)-patulolide C isolated from Penicillium urticae has been achieved from commercially available 9-decen-1-ol. Jacobsen's kinetic resolution and sequential alpha-aminooxylation and Horner-Wadsworth-Emmons (HWE) olefination followed by Yamaguchi lactonization are used as the key reaction steps. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.05.063
• 作为产物：
  描述：

  ethyl (E,4S,11R)-4-anilinooxy-11-[tert-butyl(dimethyl)silyl]oxydodec-2-enoate 在 copper diacetate 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以85%的产率得到ethyl (E,4S,11R)-11-[1-(tert-butyl)-1,1-dimethylsilyl]oxy-4-hydroxy-2-dodecenoate
  参考文献：
  名称：

  Enantioselective synthesis of (+)-patulolide C via proline-catalyzed sequential α-aminooxylation and Horner–Wadsworth–Emmons olefination

  摘要：

  The enantioselective total synthesis of (+)-patulolide C isolated from Penicillium urticae has been achieved from commercially available 9-decen-1-ol. Jacobsen's kinetic resolution and sequential alpha-aminooxylation and Horner-Wadsworth-Emmons (HWE) olefination followed by Yamaguchi lactonization are used as the key reaction steps. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.05.063

文献信息

• Enantioselective synthesis of (+)-patulolide C via proline-catalyzed sequential α-aminooxylation and Horner–Wadsworth–Emmons olefination
  作者：Gowravaram Sabitha、G. Chandrashekhar、K. Yadagiri、J.S. Yadav

  DOI：10.1016/j.tetlet.2010.05.063

  日期：2010.7

  The enantioselective total synthesis of (+)-patulolide C isolated from Penicillium urticae has been achieved from commercially available 9-decen-1-ol. Jacobsen's kinetic resolution and sequential alpha-aminooxylation and Horner-Wadsworth-Emmons (HWE) olefination followed by Yamaguchi lactonization are used as the key reaction steps. (C) 2010 Elsevier Ltd. All rights reserved.