(E)-7-(benzyloxy)hept-3-en-5-yn-2-ol | 1138138-97-2

• 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)-7-(benzyloxy)hept-3-en-5-yn-2-ol
• 英文别名: (E)-7-phenylmethoxyhept-3-en-5-yn-2-ol
• CAS: 1138138-97-2
• 化学式: C₁₄H₁₆O₂
• 分子量: 216.28
• InChiKey: SGYJCDDXBAFAOQ-XBXARRHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-7-(benzyloxy)hept-3-en-5-yn-2-ol 在 titanium(IV) isopropylate 、 L-(+)-酒石酸二乙酯 、 叔丁基过氧化氢 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 336.0h， 以38%的产率得到(R,E)-7-(benzyloxy)hept-3-en-5-yn-2-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
• 作为产物：
  描述：

  (E)-6-(benzyloxy)hex-2-en-4-ynal 、 甲基氯化镁 在 水 、 氯化铵 作用下， 以 四氢呋喃 为溶剂， 以93%的产率得到(E)-7-(benzyloxy)hept-3-en-5-yn-2-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

文献信息

• Gold catalysis in stereoselective natural product synthesis: (+)-linalool oxide, (−)-isocyclocapitelline, and (−)-isochrysotricine
  作者：Frank Volz、Sipke H. Wadman、Anja Hoffmann-Röder、Norbert Krause

  DOI：10.1016/j.tet.2008.11.104

  日期：2009.2

  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.