1-(Pentamethylsilanyl)-1,3-butadiyne

• 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: 1-(Pentamethylsilanyl)-1,3-butadiyne
• 英文别名: Pentamethyl-(ethynyl)-2-disilylacetylene；buta-1,3-diynyl-dimethyl-trimethylsilylsilane
• 化学式: C₉H₁₆Si₂
• 分子量: 180.397
• InChiKey: WMPSXFZPQBXOQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.29
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  4-硝基碘苯 、 1-(Pentamethylsilanyl)-1,3-butadiyne 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 作用下， 以 三乙胺 为溶剂， 反应 0.5h， 以57%的产率得到1-(p-Nitrophenyl)-4-(pentamethyldisilanyl)-1,3-butadiyne
  参考文献：
  名称：

  Photochemistry of 1-Aryl-4-(pentamethyldisilanyl)-1,3-butadiynes

  摘要：

  All the 1-aryl-4-(pentamethyldisilanyl)-1,3-butadiynes (1a-d) synthesized show strong phosphorescence emissions with triplet energies around 218-260 kJ/mol. Laser photolysis of 1-(p-nitrophenyl)-4-(pentamethyldisilanyl)-1,3-butadiyne (1d) in polar solvents results in the formation of an interesting transient (zwitterion species) through intramolecular electron transfer from disilanyl to the nitro group in the triplet excited state. Irradiation of 1d in methanol or ethanol gives 1-(p-nitrophenyl)-1,3-butadiyne (8) through C-Si bond cleavage from the transient. Photolysis of 1-phenyl-4-(pentamethyldisilanyl)-1,3-butadiyne (1a), 1-(1-naphthyl)-4-(pentamethyldisilanyl)-1,3-butadiyne (1b), and 1-(p-methoxyphenyl)-4-(pentamethyldisilanyl)-1,3-butadiyne (1c) in methanol yields photoaddition products (2-7) through silacyclopropene intermediates.

  DOI：

  10.1021/jo00084a031
• 作为产物：
  描述：

  (Z)-1-methoxybut-1-en-3-yne 、 一氯五甲基二硅烷 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 以73%的产率得到1-(Pentamethylsilanyl)-1,3-butadiyne
  参考文献：
  名称：

  Photochemistry of 1-Aryl-4-(pentamethyldisilanyl)-1,3-butadiynes

  摘要：

  All the 1-aryl-4-(pentamethyldisilanyl)-1,3-butadiynes (1a-d) synthesized show strong phosphorescence emissions with triplet energies around 218-260 kJ/mol. Laser photolysis of 1-(p-nitrophenyl)-4-(pentamethyldisilanyl)-1,3-butadiyne (1d) in polar solvents results in the formation of an interesting transient (zwitterion species) through intramolecular electron transfer from disilanyl to the nitro group in the triplet excited state. Irradiation of 1d in methanol or ethanol gives 1-(p-nitrophenyl)-1,3-butadiyne (8) through C-Si bond cleavage from the transient. Photolysis of 1-phenyl-4-(pentamethyldisilanyl)-1,3-butadiyne (1a), 1-(1-naphthyl)-4-(pentamethyldisilanyl)-1,3-butadiyne (1b), and 1-(p-methoxyphenyl)-4-(pentamethyldisilanyl)-1,3-butadiyne (1c) in methanol yields photoaddition products (2-7) through silacyclopropene intermediates.

  DOI：

  10.1021/jo00084a031

文献信息

• Photochemistry of 1-Aryl-4-(pentamethyldisilanyl)-1,3-butadiynes
  作者：Jang Hyuk Kwon、Seong Taek Lee、Sang Chul Shim、Mikio Hoshino

  DOI：10.1021/jo00084a031

  日期：1994.3

  All the 1-aryl-4-(pentamethyldisilanyl)-1,3-butadiynes (1a-d) synthesized show strong phosphorescence emissions with triplet energies around 218-260 kJ/mol. Laser photolysis of 1-(p-nitrophenyl)-4-(pentamethyldisilanyl)-1,3-butadiyne (1d) in polar solvents results in the formation of an interesting transient (zwitterion species) through intramolecular electron transfer from disilanyl to the nitro group in the triplet excited state. Irradiation of 1d in methanol or ethanol gives 1-(p-nitrophenyl)-1,3-butadiyne (8) through C-Si bond cleavage from the transient. Photolysis of 1-phenyl-4-(pentamethyldisilanyl)-1,3-butadiyne (1a), 1-(1-naphthyl)-4-(pentamethyldisilanyl)-1,3-butadiyne (1b), and 1-(p-methoxyphenyl)-4-(pentamethyldisilanyl)-1,3-butadiyne (1c) in methanol yields photoaddition products (2-7) through silacyclopropene intermediates.