2-bromocyclohexyl 2-oxo-2-phenylacetate | 924654-97-7

• 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: 2-bromocyclohexyl 2-oxo-2-phenylacetate
• 英文别名: [(1R,2R)-2-bromocyclohexyl] 2-oxo-2-phenylacetate
• CAS: 924654-97-7
• 化学式: C₁₄H₁₅BrO₃
• 分子量: 311.175
• InChiKey: RYVXUSKVWCHRJW-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-bromocyclohexyl 2-oxo-2-phenylacetate 在 sodium azide 、 15-冠醚-5 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.33h， 生成 (1R,2S)-cis-2-azidocyclohexanol
  参考文献：
  名称：

  Single Enantiomer Epoxides by Bromomandelation of Prochiral Alkenes

  摘要：

  A combination of mandelic acid and N-bromosuccinimide efficiently converts prochiral alkenes into a readily separable 1:1 mixture of the bromomandelates. The diastereomerically pure bromomandelates are then converted into a variety of enantiomerically pure products. Terminal alkenes are converted into enantiomerically pure epoxides. Cyclohexene is converted into enantiomerically pure cis-2-azidocyclohexanol and cis-2-phenylthiocyclohexanol.

  DOI：

  10.1021/jo061818r
• 作为产物：
  描述：

  (S)-(+)-扁桃酸 在 2,6-二甲基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 2-bromocyclohexyl 2-oxo-2-phenylacetate
  参考文献：
  名称：

  Single Enantiomer Epoxides by Bromomandelation of Prochiral Alkenes

  摘要：

  A combination of mandelic acid and N-bromosuccinimide efficiently converts prochiral alkenes into a readily separable 1:1 mixture of the bromomandelates. The diastereomerically pure bromomandelates are then converted into a variety of enantiomerically pure products. Terminal alkenes are converted into enantiomerically pure epoxides. Cyclohexene is converted into enantiomerically pure cis-2-azidocyclohexanol and cis-2-phenylthiocyclohexanol.

  DOI：

  10.1021/jo061818r

文献信息

• First asymmetric intermolecular bromoesterification catalyzed by chiral Brønsted acid
  作者：Guang-xun Li、Qing-quan Fu、Xiao-mei Zhang、Jun Jiang、Zhuo Tang

  DOI：10.1016/j.tetasy.2012.02.016

  日期：2012.2

  The first successful enantioselective intermolecular bromoesterification was realized by using a chiral phosphoric acid as a catalyst. The reaction was optimized after screening 2-aminopyridine based basic catalysts. cinchona alkaloid based basic catalysts, and binol backbone based Bronsted acid catalysts. Up to 70% ee and a moderate yield were achieved under the optimized condition. An ion-pair mechanism has been suggested in order to explain the reaction results. (C) 2012 Elsevier Ltd. All rights reserved.
• Single Enantiomer Epoxides by Bromomandelation of Prochiral Alkenes
  作者：Douglass F. Taber、Jiang-lin Liang

  DOI：10.1021/jo061818r

  日期：2007.1.1

  A combination of mandelic acid and N-bromosuccinimide efficiently converts prochiral alkenes into a readily separable 1:1 mixture of the bromomandelates. The diastereomerically pure bromomandelates are then converted into a variety of enantiomerically pure products. Terminal alkenes are converted into enantiomerically pure epoxides. Cyclohexene is converted into enantiomerically pure cis-2-azidocyclohexanol and cis-2-phenylthiocyclohexanol.