(4Z,17Z)-4-hydroxymethyl-1-trimethylsilyl-4,17-docosadien-1-yn-3-ol | 1256266-66-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4Z,17Z)-4-hydroxymethyl-1-trimethylsilyl-4,17-docosadien-1-yn-3-ol
• 英文别名: (2Z)-2-[(Z)-octadec-13-enylidene]-5-trimethylsilylpent-4-yne-1,3-diol
• CAS: 1256266-66-6
• 化学式: C₂₆H₄₈O₂Si
• 分子量: 420.751
• InChiKey: NCXBMMJPYXBWEP-VLVTYVNMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.18
• 重原子数：
  29
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4Z,17Z)-4-hydroxymethyl-1-trimethylsilyl-4,17-docosadien-1-yn-3-ol 、 三甲基乙酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以81%的产率得到
  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：

  3-三甲基甲硅烷基丙炔醛 、 (2Z,15Z)-2-iodo-2,15-icosadien-1-ol 在 甲基锂 、 叔丁基锂 作用下， 以 乙醚 、 正戊烷 为溶剂， 反应 1.25h， 以80%的产率得到(4Z,17Z)-4-hydroxymethyl-1-trimethylsilyl-4,17-docosadien-1-yn-3-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.