(S)-(-)-2-methyl-2-phenylcyclohexanone | 67074-38-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-(-)-2-methyl-2-phenylcyclohexanone
• 英文别名: (S)-2-methyl-2-phenylcyclohexanone；(2S)-2-methyl-2-phenylcyclohexan-1-one
• CAS: 67074-38-8
• 化学式: C₁₃H₁₆O
• 分子量: 188.269
• InChiKey: NKJLGNHULJVJGL-ZDUSSCGKSA-N

物化性质

• 沸点：
  295.6±29.0 °C(Predicted)
• 密度：
  1.014±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-(-)-2-methyl-2-phenylcyclohexanone 在 正丁基锂 、 cerium(III) chloride 、 伯吉斯试剂 、 臭氧 、 三苯基膦 作用下， 以 苯 为溶剂， 反应 26.5h， 生成 (S)-(+)-1,2-diphenyl-2-methyl-6-hepten-1-one
  参考文献：
  名称：

  Intramolecular nucleophilic addition to unsaturated carbon. Dependence of cyclization efficiency on the method of carbon-carbon bond cleavage utilized to generate the reactive species

  摘要：

  DOI：

  10.1021/jo00282a019
• 作为产物：
  描述：

  2-苯基环己酮 在 盐酸 、 正丁基锂 作用下， 反应 10.17h， 生成 (S)-(-)-2-methyl-2-phenylcyclohexanone
  参考文献：
  名称：

  Enders, Dieter; Zamponi, Andreas; Schaefer, Thomas, Chemische Berichte, 1994, vol. 127, # 9, p. 1707 - 1722

  摘要：

  DOI：

文献信息

• Stereospecific Construction of Contiguous Quaternary All-Carbon Centers by Oxidative Ring Contraction
  作者：Xin Yu、Jiadong Hu、Zhigao Shen、Hui Zhang、Jin-Ming Gao、Weiqing Xie

  DOI：10.1002/anie.201609975

  日期：2017.1.2

  ketones was facilitated by the action of H2O2 under operationally simple and environmentally benign reaction conditions. The process was highly regioselective and enables stereospecific construction of contiguous quaternary all‐carbon centers from stereodefined all‐substituted all‐cyclic ketones. The asymmetric syntheses of (+)‐cuparene and (+)‐tochuinyl acetate were also successively achieved by taking advantage

  在操作简单和环境友好的反应条件下，H 2 O 2的作用促进了环状α-甲酰基酮的氧化环收缩。该过程具有高度的区域选择性，并能够从立体定义的全取代的全环酮立体构筑连续的季碳全碳中心。利用该新方案还成功实现了（+）-cuparene和（+）-tochuinyl乙酸酯的不对称合成。
• Stereoselective Synthesis of Quaternary Benzylic Carbons Using <i>C</i><i>₂</i> Symmetric Imidazolines and Tetrahydrofuran as Electrophile
  作者：Peter I. Dalko、Yves Langlois

  DOI：10.1021/jo980289r

  日期：1998.11.1

  Alkylative ring opening of tetrahydrofuran in the presence of 9-BBN triflate is studied. Dianions derived from Ct symmetric imidazolines induce excellent to modest acyclic diastereoselectivity to form quaternary benzylic centers, using the 9-BBN triflate/THF system or methyl iodide as electrophiles. The direction of the stereoinduction is consistent in both cases. Absolute configuration for the newly created stereogenic center was established by chemical correlation. Low-temperature NMR studies of the dilithiated intermediates 42 and 43 suggest the presence of N- and C-metalated compounds, where the metal-bearing benzylic carbon is sp(3) hybridized.