(2S,trans)-dec-5,9-diene-1,2-diol | 1197370-38-9

• 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: (2S,trans)-dec-5,9-diene-1,2-diol
• CAS: 1197370-38-9
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: UBXLKCFZSINLPI-PORFMDCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.64
• 重原子数：
  12.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (2S,trans)-dec-5,9-diene-1,2-diol 在 potassium osmate(VI) dihydrate 、 十二/十四烷基二甲基氧化胺 、 三氟乙酸 作用下， 以 水 、 丙酮 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of 10 stereochemically distinct bis-tetrahydrofuran intermediates for creating a library of 64 asimicin stereoisomers

  摘要：

  Stereoselective synthesis of 10 unique bifunctional stereoisomeric adjacent bis-THF intermediates (R = Bz), including 5.1-5.4, 5.7-5.9, 5.11, and 5.15-5.16, of 16 possible compounds, is described. The key steps used in the synthesis of these compounds included the rhenium(VII) oxide-mediated and the Co(modP)(2)-catalyzed trans oxidative cyclizations (OCs), the OsO4-catalyzed cis OC, and the Williamson's type etherification reactions. The remaining six bis-THF intermediates (R = Bn) can be prepared from 5.7-5.9, 5.11, and 5.15-5.16 (R = Bz) in two steps, including protection of the free alcohol as benzyl ether followed by the benzoate deprotection. These intermediates should provide access to all 64 asimicin stereoisomers; and their analogs. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2009.08.082
• 作为产物：
  描述：

  (9S)-dec-1-en-5-yne-9,10-diol 在 氨 、 sodium 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以95%的产率得到(2S,trans)-dec-5,9-diene-1,2-diol
  参考文献：
  名称：

  Synthesis of 10 stereochemically distinct bis-tetrahydrofuran intermediates for creating a library of 64 asimicin stereoisomers

  摘要：

  Stereoselective synthesis of 10 unique bifunctional stereoisomeric adjacent bis-THF intermediates (R = Bz), including 5.1-5.4, 5.7-5.9, 5.11, and 5.15-5.16, of 16 possible compounds, is described. The key steps used in the synthesis of these compounds included the rhenium(VII) oxide-mediated and the Co(modP)(2)-catalyzed trans oxidative cyclizations (OCs), the OsO4-catalyzed cis OC, and the Williamson's type etherification reactions. The remaining six bis-THF intermediates (R = Bn) can be prepared from 5.7-5.9, 5.11, and 5.15-5.16 (R = Bz) in two steps, including protection of the free alcohol as benzyl ether followed by the benzoate deprotection. These intermediates should provide access to all 64 asimicin stereoisomers; and their analogs. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2009.08.082