(E)-6-(benzyloxy)hex-2-en-4-yn-1-ol | 1138139-19-1

• 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: (E)-6-(benzyloxy)hex-2-en-4-yn-1-ol
• CAS: 1138139-19-1
• 化学式: C₁₃H₁₄O₂
• 分子量: 202.253
• InChiKey: QJJPBLXCPGEZLC-LZCJLJQNSA-N

物化性质

• 沸点：
  345.4±37.0 °C(predicted)
• 密度：
  1.089±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.76
• 重原子数：
  15.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (E)-6-(benzyloxy)hex-2-en-4-yn-1-ol 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以90%的产率得到(E)-6-(benzyloxy)hex-2-en-4-ynal
  参考文献：
  名称：

  Gold catalysis in stereoselective natural product synthesis: (+)-linalool oxide, (−)-isocyclocapitelline, and (−)-isochrysotricine

  摘要：

  A stereoselective synthesis of the tetrahydrofuran-containing natural products (2S,5R)-(+)-linalool oxide (1), (-)-isocyclocapitelline (2), and (-)-isochrysotricine (3) is reported. Key steps are the copper-mediated S(N)2'-substitution of propargyl oxiranes 7 and the gold-catalyzed cycloisomerization of dihydroxyallenes 8/17, resulting in a highly efficient center-to-axis-to-center chirality transfer. The enantioselective total synthesis of (-)-isocyclocapitelline (2) and (-)-isochrysotricine (3) allowed the elucidation of the absolute configuration of these beta-carboline natural products. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.11.104
• 作为产物：
  描述：

  ethyl (E)-6-(benzyloxy)hex-2-en-4-ynoate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以90%的产率得到(E)-6-(benzyloxy)hex-2-en-4-yn-1-ol
  参考文献：
  名称：

  Gold catalysis in stereoselective natural product synthesis: (+)-linalool oxide, (−)-isocyclocapitelline, and (−)-isochrysotricine

  摘要：

  A stereoselective synthesis of the tetrahydrofuran-containing natural products (2S,5R)-(+)-linalool oxide (1), (-)-isocyclocapitelline (2), and (-)-isochrysotricine (3) is reported. Key steps are the copper-mediated S(N)2'-substitution of propargyl oxiranes 7 and the gold-catalyzed cycloisomerization of dihydroxyallenes 8/17, resulting in a highly efficient center-to-axis-to-center chirality transfer. The enantioselective total synthesis of (-)-isocyclocapitelline (2) and (-)-isochrysotricine (3) allowed the elucidation of the absolute configuration of these beta-carboline natural products. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.11.104