trans-1,10-bis(trimethylsilyl)dec-5-ene-1,3,7,9-tetrayne

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: trans-1,10-bis(trimethylsilyl)dec-5-ene-1,3,7,9-tetrayne
• 英文别名: trimethyl-[(E)-10-trimethylsilyldec-5-en-1,3,7,9-tetraynyl]silane
• 化学式: C₁₆H₂₀Si₂
• 分子量: 268.506
• InChiKey: JXHCBRCKDZHRKS-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.31
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  0.0
• 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：

  trans-1,10-bis(trimethylsilyl)dec-5-ene-1,3,7,9-tetrayne 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 0.25h， 生成 trans-dec-5-ene-1,3,7,9-tetrayne
  参考文献：
  名称：

  Enediyne Isomers of Tetraethynylethene

  摘要：

  Three isomers of tetraethynylethene (1, C10H4) have been prepared by palladium-catalyzed Negishi coupling of a trimethylsilylbutadiynyl zinc reagent with a bromoalkene, followed by mild deprotection with potassium carbonate in methanol. The unsubstituted enynes, 3-ethynyloct-3-ene-1,5,7-triyne (2), trans-dec5-ene-1,3,7,9-tetrayne (3), and cis-dec-5-ene-1,3,7,9-tetrayne (4), exhibit modest stability at -20 degrees C but decompose rapidly at room temperature. Electronic absorption spectra of 2, 3, and 4 reveal a characteristic vibronic progression at 260-320 nm. Spectral features at shorter wavelength discriminate among the isomers, and permit the assignment of 2 and 3 as apparent dimerization products of triplet carbene H-C C-C-C C-H in matrices at low temperature. Computed relative energies of these C10H4 isomers (MP2/ 6-31G*) are 1 (14.0 kcal/ mol), 2 (6.8 kcal/ mol), 3 (0.0 kcal/ mol), and 4 (1.0 kcal/ mol).

  DOI：

  10.1021/jo052505j
• 作为产物：
  描述：

  二溴化乙炔 、 1,4-双(三甲硅基)-1,3-丁二炔 在 四(三苯基膦)钯 methyllithium lithium bromide 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 27.5h， 生成 cis-1,10-bis(trimethylsilyl)dec-5-ene-1,3,7,9-tetrayne 、 trans-1,10-bis(trimethylsilyl)dec-5-ene-1,3,7,9-tetrayne
  参考文献：
  名称：

  Enediyne Isomers of Tetraethynylethene

  摘要：

  Three isomers of tetraethynylethene (1, C10H4) have been prepared by palladium-catalyzed Negishi coupling of a trimethylsilylbutadiynyl zinc reagent with a bromoalkene, followed by mild deprotection with potassium carbonate in methanol. The unsubstituted enynes, 3-ethynyloct-3-ene-1,5,7-triyne (2), trans-dec5-ene-1,3,7,9-tetrayne (3), and cis-dec-5-ene-1,3,7,9-tetrayne (4), exhibit modest stability at -20 degrees C but decompose rapidly at room temperature. Electronic absorption spectra of 2, 3, and 4 reveal a characteristic vibronic progression at 260-320 nm. Spectral features at shorter wavelength discriminate among the isomers, and permit the assignment of 2 and 3 as apparent dimerization products of triplet carbene H-C C-C-C C-H in matrices at low temperature. Computed relative energies of these C10H4 isomers (MP2/ 6-31G*) are 1 (14.0 kcal/ mol), 2 (6.8 kcal/ mol), 3 (0.0 kcal/ mol), and 4 (1.0 kcal/ mol).

  DOI：

  10.1021/jo052505j

文献信息

• Enediyne Isomers of Tetraethynylethene
  作者：Nathan P. Bowling、Robert J. McMahon

  DOI：10.1021/jo052505j

  日期：2006.8.1

  Three isomers of tetraethynylethene (1, C10H4) have been prepared by palladium-catalyzed Negishi coupling of a trimethylsilylbutadiynyl zinc reagent with a bromoalkene, followed by mild deprotection with potassium carbonate in methanol. The unsubstituted enynes, 3-ethynyloct-3-ene-1,5,7-triyne (2), trans-dec5-ene-1,3,7,9-tetrayne (3), and cis-dec-5-ene-1,3,7,9-tetrayne (4), exhibit modest stability at -20 degrees C but decompose rapidly at room temperature. Electronic absorption spectra of 2, 3, and 4 reveal a characteristic vibronic progression at 260-320 nm. Spectral features at shorter wavelength discriminate among the isomers, and permit the assignment of 2 and 3 as apparent dimerization products of triplet carbene H-C C-C-C C-H in matrices at low temperature. Computed relative energies of these C10H4 isomers (MP2/ 6-31G*) are 1 (14.0 kcal/ mol), 2 (6.8 kcal/ mol), 3 (0.0 kcal/ mol), and 4 (1.0 kcal/ mol).