1-(p-Methoxyphenyl)-4-(pentamethyldisilanyl)-1,3-butadiyne | 154116-08-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(p-Methoxyphenyl)-4-(pentamethyldisilanyl)-1,3-butadiyne
• 英文别名: 1-(p-methoxyphenyl)-4-(pentamethyldisilanyl)buta-1,3-diyne；4-(4-Methoxyphenyl)buta-1,3-diynyl-dimethyl-trimethylsilylsilane
• CAS: 154116-08-2
• 化学式: C₁₆H₂₂OSi₂
• 分子量: 286.521
• InChiKey: BXGTZRLQNDECHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.71
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  甲醇 、 1-(p-Methoxyphenyl)-4-(pentamethyldisilanyl)-1,3-butadiyne 反应 24.0h， 以13%的产率得到1-Methoxy-4-[(E)-4-(methoxy-dimethyl-silanyl)-4-trimethylsilanyl-but-3-en-1-ynyl]-benzene
  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：

  4-碘苯甲醚 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 正丁基锂 作用下， 以 四氢呋喃 、 三乙胺 为溶剂， 反应 1.83h， 生成 1-(p-Methoxyphenyl)-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

文献信息

• Photochemistry of 1-aryl-4-(pentamethyldisilanyl)buta-1,3-diynes: photoreaction with acetone and dimethyl fumarate
  作者：Sang Chul Shim、Seong Taek Lee

  DOI：10.1039/p29940001979

  日期：——

  (4–8)via silacyclopropene intermediates. Photoreaction of 1-aryl-4-(pentamethyldisilanyl)buta-1,3-diynes with dimethyl fumarate gives two-atom insertion products (9 and 13)via silacyclopropene and/or [2 + 2] photocycloaddition products (10–12 and 14). The silacyclopropene intermediates are formed from singlet excited states in compounds 1 and 2, but from the triplet excited state in compound 3.

  的1-芳基-4-（pentamethyldisilanyl）丁-1,3-二炔（照射1 - 3 1个加合物（：用丙酮产率的位点特异性和区域选择性1）4 - 8）经由silacyclopropene中间体。1-芳基-4-（五甲基二甲硅烷基）buta-1,3-二炔与富马酸二甲酯的光反应通过硅环丙烯和/或[2 + 2]光环加成产物（10 – 12和14）生成两个原子的插入产物（9和13）。）。硅环丙烯中间体是由化合物1和2中的单重激发态形成的，但是从化合物3的三重态激发的。
• 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.