(Z)-15-icosen-2-yn-1-ol | 1256266-64-4

• 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: (Z)-15-icosen-2-yn-1-ol
• 英文别名: (Z)-icos-15-en-2-yn-1-ol
• CAS: 1256266-64-4
• 化学式: C₂₀H₃₆O
• 分子量: 292.505
• InChiKey: LHYFTJIPWNCQSH-WAYWQWQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  21
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (Z)-15-icosen-2-yn-1-ol 在 叔丁基锂 、 二异丁基氢化铝 、 碘 作用下， 以 四氢呋喃 、 正戊烷 、 甲苯 、 乙酸乙酯 为溶剂， 反应 0.67h， 以84.8 mg的产率得到(2Z,15Z)-2-iodo-2,15-icosadien-1-ol
  参考文献：
  名称：

  Total synthesis of peumusolide A, NES non-antagonistic inhibitor for nuclear export of MEK

  摘要：

  The first total synthesis of peumusolide A (1) has been achieved by combination of regio- and stereo-selective aluminum-mediated hydroiodination to 2-yn-1-ol and enantioselective reduction of 4-en-1-yn-3-one with the chiral oxazaborolidine as the key reactions. This total synthesis has unequivocally established our proposed absolute structure of 1. (C) 2010 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2010.08.025
• 作为产物：
  描述：

  在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以90%的产率得到(Z)-15-icosen-2-yn-1-ol
  参考文献：
  名称：

  Total synthesis of peumusolide A, NES non-antagonistic inhibitor for nuclear export of MEK

  摘要：

  The first total synthesis of peumusolide A (1) has been achieved by combination of regio- and stereo-selective aluminum-mediated hydroiodination to 2-yn-1-ol and enantioselective reduction of 4-en-1-yn-3-one with the chiral oxazaborolidine as the key reactions. This total synthesis has unequivocally established our proposed absolute structure of 1. (C) 2010 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2010.08.025

文献信息

• Total synthesis of peumusolide A, NES non-antagonistic inhibitor for nuclear export of MEK
  作者：Satoru Tamura、Shunsuke Doke、Nobutoshi Murakami

  DOI：10.1016/j.tet.2010.08.025

  日期：2010.10

  The first total synthesis of peumusolide A (1) has been achieved by combination of regio- and stereo-selective aluminum-mediated hydroiodination to 2-yn-1-ol and enantioselective reduction of 4-en-1-yn-3-one with the chiral oxazaborolidine as the key reactions. This total synthesis has unequivocally established our proposed absolute structure of 1. (C) 2010 Published by Elsevier Ltd.