(Z)-(4-methoxy-3-buten-1-ynyl)benzene | 56370-37-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-(4-methoxy-3-buten-1-ynyl)benzene
• 英文别名: (Z)-1-methoxy4-phenylbut-1-en-3-yne；1-Methoxy-4-phenylbut-1-en-3-in；[(3Z)-4-Methoxy-3-buten-1-ynyl]benzene；[(Z)-4-methoxybut-3-en-1-ynyl]benzene
• CAS: 56370-37-7
• 化学式: C₁₁H₁₀O
• 分子量: 158.2
• InChiKey: XGWGPYAWEXYGRI-POHAHGRESA-N

物化性质

• 沸点：
  236.7±32.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 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：

  (Z)-(4-methoxy-3-buten-1-ynyl)benzene 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 25.0h， 生成 [(Z)-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：

  碘苯 、 (Z)-1-methoxybut-1-en-3-yne 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 作用下， 以 三乙胺 为溶剂， 反应 0.83h， 以65%的产率得到(Z)-(4-methoxy-3-buten-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

文献信息

• PALLADIUM-CATALYZED CROSS-COUPLING OF ORGANOLEAD(IV) TRIACETATES WITH TERMINAL ALKYNES
  作者：Suk-Ku Kang、Hyung-Chul Ryu、Sang-Ho Lee

  DOI：10.1081/scc-100103537

  日期：2001.1

  The palladium-catalyzed carbon-carbon bond formation of organolead(IV) triacetates with terminal alkynes was accomplished with Pd2(dba)3·CHCl3 (5 mol%) and CuI (10 mol%) in the presence of NaOMe (2 equiv.) in MeOH/CH3CN (1:1) at room temperature.

  在 NaOMe（2 当量）存在下，钯催化的有机铅 (IV) 三乙酸酯与末端炔烃的碳-碳键形成是用 Pd2(dba)3·CHCl3 (5 mol%) 和 CuI (10 mol%) 完成的在 MeOH/CH3CN (1:1) 中，室温。
• Regio- and stereoselective vinylic substitution reactions of α-haloenyne sulfones
  作者：Mitsuhiro Yoshimatsu、Junko Hasegawa

  DOI：10.1016/0040-4039(96)01682-6

  日期：1996.10

  The nucleophilic vinylic substitution reaction of (E)-α-haloenyne sulfones 2, 5–8 with sodium alkoxides proceeded regioselectively to give (E)-α-alkoxyenyne sulfones 9–17 in high yields with exclusive retention of their configuration.

  的亲核乙烯基取代反应（ë） - α -haloenyne砜2，5-8与醇钠进行区域选择性地得到（ë） - α -alkoxyenyne砜9-17以高收率和它们的配置的排他性保留。
• Coupling reactions of methoxybutenynyl copper - a facile route to substituted indoles
  作者：George A. Kraus、Kevin Frazier

  DOI：10.1016/s0040-4039(01)85592-1

  日期：1978.1
• 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.