1(e),2(e),6(e)-triphenyl-4-oxocyclohexane-1(a)-carbonitrile | 58305-67-2

• 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: 1(e),2(e),6(e)-triphenyl-4-oxocyclohexane-1(a)-carbonitrile
• CAS: 58305-67-2
• 化学式: C₂₅H₂₁NO
• 分子量: 351.448
• InChiKey: HUFNWVLCSKBRCC-QEIWAGNOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.38
• 重原子数：
  27.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  40.86
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1(e),2(e),6(e)-triphenyl-4-oxocyclohexane-1(a)-carbonitrile 在 溴 作用下， 以 溶剂黄146 为溶剂， 以88%的产率得到3(e),5(e)-Dibrom-4-oxo-1(e),2(e),6(e)-triphenyl-1-cyclohexancarbonitril
  参考文献：
  名称：

  Ebner, Ulrich; Kucklaender, Carola; Kuehn, Reimund, Liebigs Annalen der Chemie, 1982, # 12, p. 2172 - 2177

  摘要：

  DOI：
• 作为产物：
  描述：

  在 盐酸 、 氢氧化钾 作用下， 以 二甲基亚砜 、 丙酮 为溶剂， 反应 19.5h， 生成 1(e),2(e),6(e)-triphenyl-4-oxocyclohexane-1(a)-carbonitrile
  参考文献：
  名称：

  On the Stereochemistry of Diaryl-Substituted Cyclohexanones Formed by Michael Reactions. Trans to Cis Isomerization of Their Ketals under Basic Conditions

  摘要：

  The stereochemistry of C-1-substituted 2,6-diphenylcyclohexan-4-ones 1-3 prepared by Michael reactions has been investigated. While preparations of these compounds have been reported over the past 70 years, in many instances the correct stereochemistry at C-2 (6) and, in some instances at C-1, was uncertain. We show here that in one case in which two identical substituents (CN) are present at C-1, it is possible to isomerize the initially formed trans isomer Id to the cis isomer 3f. When a cyano group and a dissimilar substituent are present at C-1, the initially formed trans isomer may be isomerized to the cis compound. The stereochemistry is vertified by NMR spectroscopy and by X-ray analysis. Reaction of the ethylene ketals (4 and 5) of these ketones with KOH in DMSO at elevated temperatures gives rise to cis products, and deuterium-labeling studies demonstrated the acidity of the benzylic hydrogen at C-2 (6). Isomerization was evident since the trans ketal 4a and the cis ketal 4b gave the same amide 6a. H-1 and C-13 NMR spectra provided conclusive evidence for the cis - trans rearrangement.

  DOI：

  10.1021/jo9801059

文献信息

• EBNER, U.;KUCKLAENDER, C.;KUEHN, R.;CHARAF, A.;OTTO, H. -H., LIEBIGS ANN. CHEM., 1982, N 12, 2172-2177
  作者：EBNER, U.、KUCKLAENDER, C.、KUEHN, R.、CHARAF, A.、OTTO, H. -H.

  DOI：——

  日期：——