2,5-dimethyl-3,4-diphenylcyclopentanone

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2,5-dimethyl-3,4-diphenylcyclopentanone
• 英文别名: (2S,3R,4R,5S)-2,5-dimethyl-3,4-diphenylcyclopentan-1-one
• 化学式: C₁₉H₂₀O
• 分子量: 264.367
• InChiKey: YOPQDPIXXPUUCD-LBTBCDHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 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-1,2-二苯乙烯 、 2,4-二溴-3-戊酮 在 diiron nonacarbonyl 作用下， 生成 2,5-dimethyl-3,4-diphenylcyclopentanone
  参考文献：
  名称：

  Carbon-carbon bond formation promoted by transition metal carbonyls. 20. Iron carbonyl promoted reaction of .alpha.,.alpha.'-dibromo ketones and aromatic olefins leading to 3-arylcyclopentanones. The [3 + 2] cycloaddition involving an allylic cation

  摘要：

  DOI：

  10.1021/ja00474a022

文献信息

• Organoaluminum-Mediated Interrupted Nazarov Reaction
  作者：Yonghoon Kwon、Robert McDonald、Frederick G. West

  DOI：10.1002/anie.201303996

  日期：2013.8.12

  InternAl delivery: Organoaluminum reagents activate 1,4‐dien‐3‐ones for Nazarov electrocyclization (see scheme), then transfer a substituent to the resulting cyclopentenyl cation with moderate to complete regioselectivity and diastereoselectivity.

  内部递送：有机铝试剂激活Nazarov电环化反应的1,4-二烯基-3-酮（参见方案），然后将取代基转移到生成的环戊烯基阳离子上，具有中等至完全的区域选择性和非对映选择性。
• The reductive Nazarov cyclization
  作者：Sören Giese、F.G. West

  DOI：10.1016/s0040-4039(98)01934-0

  日期：1998.11

  Tri- and tetrasubstituted 1,4-dien-3-ones 1 were treated with Lewis acid in the presence of triethylsilane, furnishing either silyl enol ethers 4 or cyclopentanones 5 in good yields, depending upon work-up conditions. This reaction is presumed to occur through oxyallyl intermediate 3, which undergoes intermolecular hydride transfer and O-silylation to give 4. In most cases, only 2 equiv. of silane was required, and catalytic amounts of Lewis acid could be used. Trienone substrate 7 was found to undergo clean conversion to tricyclic ether 8, indicating fast capture of the oxyallyl intermediate by the pendant olefin. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Ionic Hydrogenation of Oxyallyl Intermediates: The Reductive Nazarov Cyclization
  作者：Sören Giese、F.G. West

  DOI：10.1016/s0040-4020(00)00866-8

  日期：2000.12

  Cyclization of tri- and tetrasubstituted dienones 1 under Lewis acidic conditions in the presence of triethylsilane led to formation of either silyl enol ethers 6 or cyclopentanones 7 in good to excellent yields, depending on work-up conditions. The proposed mechanism involves initial Nazarov cyclization to give oxyallyl intermediates 5, which are intercepted via intermolecular transfer of hydride. The reactions proceeded cleanly with as little as 2 equiv. of silane and in most cases catalytic amounts of Lewis acid could be used. Trapping with Et3SiD occurs at the less substituted terminus in unsymmetrical cases. (C) 2000 Elsevier Science Ltd. All rights reserved.