2,4-diphenyl-3-benzylidenepentane

• 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: 2,4-diphenyl-3-benzylidenepentane
• 英文别名: (3-Benzylidene-4-phenylpentan-2-yl)benzene
• 化学式: C₂₄H₂₄
• 分子量: 312.455
• InChiKey: IZVRLZKMCHCBAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  苯乙烯 在 iron(III) chloride 、 双三氟甲烷磺酰亚胺银盐 作用下， 以 1,4-二氧六环 为溶剂， 反应 18.0h， 生成 (E)-1,3-diphenyl-1-butene 、 2,4-diphenyl-3-benzylidenepentane
  参考文献：
  名称：

  铁催化苯乙烯选择性头对尾二聚反应

  摘要：

  阳离子铁盐和络合物催化苯乙烯衍生物从头到尾的二聚反应，形成相应的二聚体，具有良好或优异的收率和立体选择性。特别是，使用膦-铁（III）配合物可以回收和再利用催化剂。抗衡阴离子在活性和选择性中都起着重要作用。这些催化剂构成了基于有毒且昂贵的后期过渡金属的催化剂的替代品。

  DOI：

  10.1002/adsc.201000096

文献信息

• Reactions of the Lithium Salts of the Tribenzylidenemethane Dianion, Diphenylacetone Dianion, and Related Compounds
  作者：Ortrun Witt、Harald Mauser、Thomas Friedl、Dieter Wilhelm、Timothy Clark

  DOI：10.1021/jo971113c

  日期：1998.2.1

  Potentially synthetically useful reactions of the dilithium salts of the title dianions have been investigated, Electrophilic quenching with a variety of reagents usually leads to the expected products in good yield. Quenching the diphenylacetone dianion with 1 equiv of trimethylchlorosilane, however, gives a good yield of 1,3-diphenylallene obtained by formal elimination of a trimethylsiloxy anion from an intermediate monoquenched monoanion salt. NMR studies, however, do not reveal the intermediacy of the 1,3-diphenyl-2-(trimethylsiloxy)allyl anion but rather suggest that the initial reaction site is at carbon, rather than oxygen, Oxidation of the dianions leads either to ring closure or dimerization for the tribenzylidenemethane dianion and to dimerization for the diphenylacetone dianion. The dimerization reactions are stereospecific, both with respect to the two new stereocenters produced and for the double bonds of the bis-silyl enol ether products if the dimeric bis-enolate dianion products are quenched with trimethylchlorosilane.