(4Z,17Z)-4-pivaloyloxymethyl-1-trimethylsilyl-4,17-docosadien-1-yn-3-one | 1256266-62-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4Z,17Z)-4-pivaloyloxymethyl-1-trimethylsilyl-4,17-docosadien-1-yn-3-one
• 英文别名: [(2Z,15Z)-2-(3-trimethylsilylprop-2-ynoyl)icosa-2,15-dienyl] 2,2-dimethylpropanoate
• CAS: 1256266-62-2
• 化学式: C₃₁H₅₄O₃Si
• 分子量: 502.853
• InChiKey: VVGIYYTYBRPWMY-DGAWCVGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.99
• 重原子数：
  35
• 可旋转键数：
  21
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4Z,17Z)-4-pivaloyloxymethyl-1-trimethylsilyl-4,17-docosadien-1-yn-3-one 在 硼烷四氢呋喃络合物 、 (S)-2-甲基-CBS-恶唑硼烷 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 以82%的产率得到(S)-(4Z,17Z)-4-pivaloyloxymethyl-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
• 作为产物：
  描述：

  在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以91%的产率得到(4Z,17Z)-4-pivaloyloxymethyl-1-trimethylsilyl-4,17-docosadien-1-yn-3-one
  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.