(S)-(-)-(Z)-3-(1,2-diphenylvinyl)cyclohexanone | 1160580-98-2

• 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: (S)-(-)-(Z)-3-(1,2-diphenylvinyl)cyclohexanone
• 英文别名: (3S)-3-[(Z)-1,2-diphenylethenyl]cyclohexan-1-one
• CAS: 1160580-98-2
• 化学式: C₂₀H₂₀O
• 分子量: 276.378
• InChiKey: HFORCQRAPPYMPX-OFBHVFLISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  (2R,3R)-(-)-2,3-丁二醇 、 (S)-(-)-(Z)-3-(1,2-diphenylvinyl)cyclohexanone 在 对甲苯磺酸 作用下， 反应 12.0h， 以93%的产率得到(2R,3R,7S)-(-)-7-((Z)-1,2-diphenylvinyl)-2,3-dimethyl-1,4-dioxaspiro[4,5]decane
  参考文献：
  名称：

  Enantioselective Synthesis of β-Substituted Cyclic Ketones via Cobalt-Catalyzed Asymmetric Reductive Coupling of Alkynes with Alkenes

  摘要：

  A CoI2/(R)-BINAP, Zn, ZnI2, H2O system efficiently catalyzes the intermolecular asymmetric reductive coupling of alkynes with cyclic enones to afford highly regio- and enantioselective beta-alkenyl cyclic ketones. A possible mechanism that involves the formation of a cobaltacyclopentene intermediate from the alkyne and cyclic enone is proposed.

  DOI：

  10.1021/ja201827j
• 作为产物：
  描述：

  2-环己烯-1-酮 、 二苯基乙炔 在 水 、 (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl 、 cobalt(II) iodide 、 zinc(II) iodide 、 锌 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以67%的产率得到(S)-(-)-(Z)-3-(1,2-diphenylvinyl)cyclohexanone
  参考文献：
  名称：

  Enantioselective Synthesis of β-Substituted Cyclic Ketones via Cobalt-Catalyzed Asymmetric Reductive Coupling of Alkynes with Alkenes

  摘要：

  A CoI2/(R)-BINAP, Zn, ZnI2, H2O system efficiently catalyzes the intermolecular asymmetric reductive coupling of alkynes with cyclic enones to afford highly regio- and enantioselective beta-alkenyl cyclic ketones. A possible mechanism that involves the formation of a cobaltacyclopentene intermediate from the alkyne and cyclic enone is proposed.

  DOI：

  10.1021/ja201827j

文献信息

• Enantioselective Synthesis of β-Substituted Cyclic Ketones via Cobalt-Catalyzed Asymmetric Reductive Coupling of Alkynes with Alkenes
  作者：Chu-Hung Wei、Subramaniyan Mannathan、Chien-Hong Cheng

  DOI：10.1021/ja201827j

  日期：2011.5.11

  A CoI2/(R)-BINAP, Zn, ZnI2, H2O system efficiently catalyzes the intermolecular asymmetric reductive coupling of alkynes with cyclic enones to afford highly regio- and enantioselective beta-alkenyl cyclic ketones. A possible mechanism that involves the formation of a cobaltacyclopentene intermediate from the alkyne and cyclic enone is proposed.