(Z)-3,5-diphenyl-2-ethylpent-2-en-4-yn-1-ol | 250358-89-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (Z)-3,5-diphenyl-2-ethylpent-2-en-4-yn-1-ol
• 英文别名: (Z)-2-ethyl-3,5-diphenylpent-2-en-4-yn-1-ol
• CAS: 250358-89-5
• 化学式: C₁₉H₁₈O
• 分子量: 262.351
• InChiKey: CIMJGFWMSCVOBU-HTXNQAPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (Z)-3,5-diphenyl-2-ethylpent-2-en-4-yn-1-ol 在 palladium(II) iodide potassium iodide 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 45.0h， 以48%的产率得到2-benzyl-4-ethyl-3-phenylfuran
  参考文献：
  名称：

  A General and Facile Synthesis of Substituted Furans by Palladium-Catalyzed Cycloisomerization of (Z)-2-En-4-yn-1-ols

  摘要：

  A general and facile synthesis of furans, based on Pd(II)-catalyzed cycloisomerization of (Z)-2-en-4-yn-1-ols, is described. Cycloisomerization reactions are carried out at 25-100 degrees C in the presence of a very simple catalytic system, consisting of K2PdI4, under essentially neutral conditions. This new methodology is very versatile and can be applied to the synthesis of a variety of substituted furans, including particularly fragile, naturally occurring furans such as rosefuran. Efficient synthetic approaches for the regioselective synthesis of suitably substituted (Z)-2-en-4-yn-1-ols have been developed.

  DOI：

  10.1021/jo990847h
• 作为产物：
  描述：

  苯乙炔 、 (Z)-2-ethyl-3-iodo-3-phenylprop-2-en-1-ol 在 四(三苯基膦)钯 四氢吡咯 、 copper(l) iodide 作用下， 反应 4.0h， 生成 (Z)-3,5-diphenyl-2-ethylpent-2-en-4-yn-1-ol
  参考文献：
  名称：

  A General and Facile Synthesis of Substituted Furans by Palladium-Catalyzed Cycloisomerization of (Z)-2-En-4-yn-1-ols

  摘要：

  A general and facile synthesis of furans, based on Pd(II)-catalyzed cycloisomerization of (Z)-2-en-4-yn-1-ols, is described. Cycloisomerization reactions are carried out at 25-100 degrees C in the presence of a very simple catalytic system, consisting of K2PdI4, under essentially neutral conditions. This new methodology is very versatile and can be applied to the synthesis of a variety of substituted furans, including particularly fragile, naturally occurring furans such as rosefuran. Efficient synthetic approaches for the regioselective synthesis of suitably substituted (Z)-2-en-4-yn-1-ols have been developed.

  DOI：

  10.1021/jo990847h

文献信息

• An Efficient and General Synthesis of Furan-2-acetic Esters by Palladium-Catalyzed Oxidative Carbonylation of (<i>Z</i>)-2-En-4-yn-1-ols
  作者：Bartolo Gabriele、Giuseppe Salerno、Francesca De Pascali、Mirco Costa、Gian Paolo Chiusoli

  DOI：10.1021/jo990848+

  日期：1999.10.1

  A variety of (Z)-2-en-4-yn-1-ols have been carbonylated under oxidative conditions to give substituted furan-a-acetic esters in good yields. The cyclization-alkoxycarbonylation process occurs in alcoholic media at 50-70 degrees C and under 100 atm pressure of a 9:1 mixture of carbon monoxide and air in the presence of catalytic amounts of PdI2 in conjunction with KI. The proposed reaction pathway involves the in situ isomerization of the initially formed (E)-2-[(alkoxycarbonyl)methylene]-2,5-dihydrofuran species, which in some cases have been isolated and shown to be the intermediates.