(S,E)-3-methyl-1,4,5-triphenylpent-4-en-1-one | 1374988-81-4

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: (S,E)-3-methyl-1,4,5-triphenylpent-4-en-1-one
• 英文别名: (E,3S)-3-methyl-1,4,5-triphenylpent-4-en-1-one
• CAS: 1374988-81-4
• 化学式: C₂₄H₂₂O
• 分子量: 326.438
• InChiKey: KDSMVVZWRSZWEZ-IPCAQAEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  反式-1-苯基-2-丁烯-1-酮 、 (E)-(1,2-diphenylvinyl)boronic acid 在 [IrCl((S,S)-ferrocenyl-(tetrafluorobenzobarrelene)*)]₂ 、 caesium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 14.0h， 以99%的产率得到(S,E)-3-methyl-1,4,5-triphenylpent-4-en-1-one
  参考文献：
  名称：

  Asymmetric conjugate addition of cis-2-arylethenylboronic acids catalyzed by chiral diene/rhodium complexes: 1,4-rhodium shift from alkenylrhodium to arylrhodium intermediates

  摘要：

  The reaction of (E)-1,2-diphenylethenylboronic acid 1 with 2-cyclohexenone in the presence of a chiral diene/rhodium catalyst (5 mol %) gave 3-[2-((E)-2-phenylethenyl)phenyl]cyclohexanone in 99% yield with 98.7% ee; the catalytic cycle involves a 1,4-rhodium shift from a 2-phenylethenylrhodium to an ortho-alkenylphenylrhodium intermediate. In the reaction of 1 with (E)-1-phenyl-2-buten-1-one, either the tandem 1,4-shift/arylation product or the direct alkenylation product is formed selectively by an appropriate choice of chiral diene ligand. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.03.004

文献信息

• Asymmetric conjugate addition of cis-2-arylethenylboronic acids catalyzed by chiral diene/rhodium complexes: 1,4-rhodium shift from alkenylrhodium to arylrhodium intermediates
  作者：Keigo Sasaki、Tamio Hayashi

  DOI：10.1016/j.tetasy.2012.03.004

  日期：2012.3

  The reaction of (E)-1,2-diphenylethenylboronic acid 1 with 2-cyclohexenone in the presence of a chiral diene/rhodium catalyst (5 mol %) gave 3-[2-((E)-2-phenylethenyl)phenyl]cyclohexanone in 99% yield with 98.7% ee; the catalytic cycle involves a 1,4-rhodium shift from a 2-phenylethenylrhodium to an ortho-alkenylphenylrhodium intermediate. In the reaction of 1 with (E)-1-phenyl-2-buten-1-one, either the tandem 1,4-shift/arylation product or the direct alkenylation product is formed selectively by an appropriate choice of chiral diene ligand. (C) 2012 Elsevier Ltd. All rights reserved.