1-Ethynyl-2-hex-5-en-1-ynylcyclopentene | 210829-17-7

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 1-Ethynyl-2-hex-5-en-1-ynylcyclopentene
• CAS: 210829-17-7
• 化学式: C₁₃H₁₄
• 分子量: 170.254
• InChiKey: XXKMPZGMZAGRLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  1-Ethynyl-2-hex-5-en-1-ynylcyclopentene 、 alkaline earth salt of/the/ methylsulfuric acid 在 对甲苯磺酸 作用下， 生成 4-Methyl-3-oxatetracyclo[10.4.0.02,6.07,11]hexadeca-1(16),2(6),4,7(11),12,14-hexaene 、 2-methyl-7-methylidene-5,6,8,9-tetrahydro-4H-as-indaceno[4,5-b]furan 、 2,7-Dimethyl-4,5,6,7,8,9-hexahydro-as-indaceno[4,5-b]furan
  参考文献：
  名称：

  Coupling of Fischer Carbene Complexes with Conjugated Enediynes:  Generation of Chromium-Complexed Diradicals via the Moore Cyclization and Subsequent Radical Trapping Reactions

  摘要：

  DOI：

  10.1021/jo980300n
• 作为产物：
  描述：

  Tert-butyl-[2-(2-hex-5-en-1-ynylcyclopenten-1-yl)ethynyl]-dimethylsilane 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以92%的产率得到1-Ethynyl-2-hex-5-en-1-ynylcyclopentene
  参考文献：
  名称：

  Coupling of Fischer carbene complexes with conjugated enediynes featuring radical traps: Novel structure and reactivity features of chromium complexed arene diradical species

  摘要：

  The reaction of Fischer carbene complexes with conjugated enediynes that feature a pendant alkene group has been examined. The reaction proceeds through carbene-alkyne coupling to generate an enyne-ketene intermediate. This intermediate then undergoes Moore cyclization to generate a chromium complexed arene diradical, which then undergoes cyclization with the pendant alkene group. The radical cyclization prefers the 6-endo mode unless radical-stabilizing groups are present to favor the 5-exo mode. The intermediate diradical species were evaluated computationally in both the singlet and triplet configurations. Arene triplet diradicals feature minimal spin density at oxygen and delocalization to chromium. The 6-endo cyclization product was kinetically and thermodynamically favored. (C) 2008 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2008.08.003

文献信息

• Coupling of Fischer carbene complexes with conjugated enediynes featuring radical traps: Novel structure and reactivity features of chromium complexed arene diradical species
  作者：Yi Zhang、Tareq Irshaidat、Haixia Wang、Kris V. Waynant、Haobin Wang、James W. Herndon

  DOI：10.1016/j.jorganchem.2008.08.003

  日期：2008.10

  The reaction of Fischer carbene complexes with conjugated enediynes that feature a pendant alkene group has been examined. The reaction proceeds through carbene-alkyne coupling to generate an enyne-ketene intermediate. This intermediate then undergoes Moore cyclization to generate a chromium complexed arene diradical, which then undergoes cyclization with the pendant alkene group. The radical cyclization prefers the 6-endo mode unless radical-stabilizing groups are present to favor the 5-exo mode. The intermediate diradical species were evaluated computationally in both the singlet and triplet configurations. Arene triplet diradicals feature minimal spin density at oxygen and delocalization to chromium. The 6-endo cyclization product was kinetically and thermodynamically favored. (C) 2008 Elsevier B.V. All rights reserved.
• Coupling of Fischer Carbene Complexes with Conjugated Enediynes:  Generation of Chromium-Complexed Diradicals via the Moore Cyclization and Subsequent Radical Trapping Reactions
  作者：James W. Herndon、Haixia Wang

  DOI：10.1021/jo980300n

  日期：1998.7.1