(Z)-6-ethyl-5-iodo-5-dodecen-7-yne | 156027-53-1

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: (Z)-6-ethyl-5-iodo-5-dodecen-7-yne
• 英文别名: (Z)-6-ethyl-5-iodododec-5-en-7-yne
• CAS: 156027-53-1
• 化学式: C₁₄H₂₃I
• 分子量: 318.241
• InChiKey: MNAWZOAATLDWTK-YPKPFQOOSA-N

物化性质

• 沸点：
  321.5±25.0 °C(Predicted)
• 密度：
  1.248±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (Z)-6-ethyl-5-iodo-5-dodecen-7-yne 、 乙氧基乙炔 在 四(三苯基膦)钯 、 正丁基锂 、 zinc(II) chloride 作用下， 生成 (Z)-5-(2-ethoxyethynyl)-6-ethyldodec-5-en-7-yne
  参考文献：
  名称：

  Synthesis and Thermolysis of Enediynyl Ethyl Ethers as Precursors of Enyne−Ketenes

  摘要：

  Enediynyl ethyl ethers 14/17 were synthesized by using the Pd(PPh3)(4)-catalyzed cross-coupling reactions between enynyl iodides 13/16 and (2-ethoxyethynyl)zinc chloride. Thermolysis of these enediynyl ethyl ethers in refluxing chlorobenzene (132 degrees C) promoted a retro-ene reaction to produce enyne-ketenes, which underwent the Moore cyclization reactions to form the biradicals having a phenyl radical center and a phenoxy radical center. The presence of two radical centers in the same molecule simultaneously provided many opportunities for intramolecular decay through disproportionation, radical-radical combination, and the formation of o-quinone methide.

  DOI：

  10.1021/jo971391b
• 作为产物：
  描述：

  1-bromohexyne 、 三乙基硼 、 1-己炔 生成 (Z)-6-ethyl-5-iodo-5-dodecen-7-yne
  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：——