methyl (Z)-2-methyl-3,5-diphenyl-2-penten-4-ynoate | 94305-41-6

• 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: methyl (Z)-2-methyl-3,5-diphenyl-2-penten-4-ynoate
• 英文别名: cis-3,5-Diphenyl-2-methyl-pent-2-en-4-in-saeure-methylester；(Z)-methyl 2-methyl-3,5-diphenylpent-2-en-4-ynoate；methyl (Z)-2-methyl-3,5-diphenylpent-2-en-4-ynoate
• CAS: 94305-41-6
• 化学式: C₁₉H₁₆O₂
• 分子量: 276.335
• InChiKey: UMQZUWXFNSNRTQ-OBGWFSINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl (Z)-2-methyl-3,5-diphenyl-2-penten-4-ynoate 在 碘 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以76%的产率得到(5E)-5-[iodo(phenyl)methylidene]-3-methyl-4-phenylfuran-2-(5H)-one
  参考文献：
  名称：

  Synthesis of Isocoumarins and α-Pyrones via Electrophilic Cyclization

  摘要：

  A variety of substituted isocoumarins and alpha-pyrones are readily prepared in excellent yields under very mild reaction conditions by the reaction of o-(1-alkynyl)benzoates and (Z)-2-alken-4-ynoates with ICI, I-2, PhSeCl, p-O2NC6H4SCl, and HI. This methodology accommodates various alkynyl esters and has been successfully extended to the synthesis of polycyclic aromatic and biaryl compounds.

  DOI：

  10.1021/jo034308v
• 作为产物：
  描述：

  苯乙炔 、 methyl (Z)-3-iodo-2-methyl-3-phenyl-2-propenoate 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 三乙胺 作用下， 以93%的产率得到methyl (Z)-2-methyl-3,5-diphenyl-2-penten-4-ynoate
  参考文献：
  名称：

  Synthesis of Isocoumarins and α-Pyrones via Electrophilic Cyclization

  摘要：

  A variety of substituted isocoumarins and alpha-pyrones are readily prepared in excellent yields under very mild reaction conditions by the reaction of o-(1-alkynyl)benzoates and (Z)-2-alken-4-ynoates with ICI, I-2, PhSeCl, p-O2NC6H4SCl, and HI. This methodology accommodates various alkynyl esters and has been successfully extended to the synthesis of polycyclic aromatic and biaryl compounds.

  DOI：

  10.1021/jo034308v

文献信息

• Yoshikawa, Takashi; Mori, Seiji; Shindo, Mitsuru, Journal of the American Chemical Society, 2009, vol. 131, p. 2092 - 2093
  作者：Yoshikawa, Takashi、Mori, Seiji、Shindo, Mitsuru

  DOI：——

  日期：——
• Synthesis of Isocoumarins and α-Pyrones via Electrophilic Cyclization
  作者：Tuanli Yao、Richard C. Larock

  DOI：10.1021/jo034308v

  日期：2003.7.1

  A variety of substituted isocoumarins and alpha-pyrones are readily prepared in excellent yields under very mild reaction conditions by the reaction of o-(1-alkynyl)benzoates and (Z)-2-alken-4-ynoates with ICI, I-2, PhSeCl, p-O2NC6H4SCl, and HI. This methodology accommodates various alkynyl esters and has been successfully extended to the synthesis of polycyclic aromatic and biaryl compounds.