(Z)-4-butyl-5-ethyl-7-phenyl-4-heptene-2,6-diyn-1-ol

• 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)-4-butyl-5-ethyl-7-phenyl-4-heptene-2,6-diyn-1-ol
• 英文别名: (4Z)-4-(1-phenylpent-1-yn-3-ylidene)oct-2-yn-1-ol
• 化学式: C₁₉H₂₂O
• 分子量: 266.383
• InChiKey: VVGXRJASIZGMRG-HNENSFHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-己炔 在 四(三苯基膦)钯 copper(l) iodide 、 正丁胺 作用下， 反应 4.0h， 生成 (Z)-4-butyl-5-ethyl-7-phenyl-4-heptene-2,6-diyn-1-ol
  参考文献：
  名称：

  Stereoselective Synthesis of Enediynes and Enyne Allenes Having a Tetrasubstituted Central Carbon-Carbon Double Bond

  摘要：

  The trimethyltin-substituted alkenylborane 2 was prepared by simply treating Lithium 1-alkynyltrialkylborate 1, readily obtained from the corresponding trialkylborane and 1-lithio-1-alkyne, with trimethyltin chloride. The transformation is stereoselective with the boron and tin appendages cis to each other. Sequential treatment of 2 generated in situ with n-butyllithium, CuBrSMe(2), 1-bromo-1-alkyne, and iodine furnished the corresponding enynyl iodide 3 in a single operation. Similarly, ene-allenic iodide 7a was produced by coupling with methanesulfonate 6. The subsequent Pd(PPh(3))(4)-catalyzed cross-coupling between 3 or 7a with 1-alkynylzinc chloride or with l-alkyne in the presence of CuI/n-BuNH(2) produced enediyne 4 or enyne-allene 8 having a tetrasubstituted central double bond. The use of propargyl alcohol for coupling with 7a resulted in the formation of 10, presumably because a facile cycloaromatization reaction of the anticipated enyne-allene 9 occurred.

  DOI：

  10.1021/jo00096a014

文献信息

• Wang Zhongguo, Wang Kung K., J. Org. Chem, 59 (1994) N 17, S 4738-4742
  作者：Wang Zhongguo, Wang Kung K.

  DOI：——

  日期：——
• Stereoselective Synthesis of Enediynes and Enyne Allenes Having a Tetrasubstituted Central Carbon-Carbon Double Bond
  作者：Zhongguo Wang、Kung K. Wang

  DOI：10.1021/jo00096a014

  日期：1994.8

  The trimethyltin-substituted alkenylborane 2 was prepared by simply treating Lithium 1-alkynyltrialkylborate 1, readily obtained from the corresponding trialkylborane and 1-lithio-1-alkyne, with trimethyltin chloride. The transformation is stereoselective with the boron and tin appendages cis to each other. Sequential treatment of 2 generated in situ with n-butyllithium, CuBrSMe(2), 1-bromo-1-alkyne, and iodine furnished the corresponding enynyl iodide 3 in a single operation. Similarly, ene-allenic iodide 7a was produced by coupling with methanesulfonate 6. The subsequent Pd(PPh(3))(4)-catalyzed cross-coupling between 3 or 7a with 1-alkynylzinc chloride or with l-alkyne in the presence of CuI/n-BuNH(2) produced enediyne 4 or enyne-allene 8 having a tetrasubstituted central double bond. The use of propargyl alcohol for coupling with 7a resulted in the formation of 10, presumably because a facile cycloaromatization reaction of the anticipated enyne-allene 9 occurred.