(Z)-5-butyl-6-ethyl-2-methyl-5-dodecene-3,7-diyn-2-ol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-5-butyl-6-ethyl-2-methyl-5-dodecene-3,7-diyn-2-ol
• 英文别名: (Z)-5-butyl-6-ethyl-2-methyldodec-5-en-3,7-diyn-2-ol
• 化学式: C₁₉H₃₀O
• 分子量: 274.447
• InChiKey: BCHULTUMAVHQBI-ZCXUNETKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.68
• 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-bromohexyne 在 四(三苯基膦)钯 copper(l) iodide 、 正丁胺 作用下， 反应 4.0h， 生成 (Z)-5-butyl-6-ethyl-2-methyl-5-dodecene-3,7-diyn-2-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：——