[(1R)-2-(3,4-dimethoxyphenyl)cyclohex-2-en-1-yl] acetate | 216006-07-4

• 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: [(1R)-2-(3,4-dimethoxyphenyl)cyclohex-2-en-1-yl] acetate
• CAS: 216006-07-4
• 化学式: C₁₆H₂₀O₄
• 分子量: 276.332
• InChiKey: UPVIUOIEXQITGW-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(1R)-2-(3,4-dimethoxyphenyl)cyclohex-2-en-1-yl] acetate 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以98%的产率得到(+)-2-(3,4-dimethoxyphenyl)cyclohex-2-en-1-ol
  参考文献：
  名称：

  Asymmetric synthesis of sceletium alkaloids: (−)-mesembrine, (+)-sceletium A-4, (+)-tortuosamine and (+)-N-formyltortuosamine

  摘要：

  Three procedures for the transformation of achiral 1-(3,4-dimethoxyphenyl)cyclohexene into enantiomerically pure 2-(3,4-dimethoxyphenyl)cyclohex-2-en-1-ol have been established at first. Utilizing the (-)-cyclohexenol thus obtained, the four titled Sceletium alkaloids have been synthesized in the natural enantiomeric forms. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01689-x
• 作为产物：
  描述：

  [(1S,2R)-2-(3,4-dimethoxyphenyl)-2-hydroxycyclohexyl] 3-chlorobenzoate 在 吡啶 、 lipase PS (Pseudomonas cepacia, Amano) 、 potassium carbonate 、 三氯氧磷 作用下， 以 甲醇 为溶剂， 反应 96.0h， 生成 [(1R)-2-(3,4-dimethoxyphenyl)cyclohex-2-en-1-yl] acetate
  参考文献：
  名称：

  Asymmetric synthesis of sceletium alkaloids: (−)-mesembrine, (+)-sceletium A-4, (+)-tortuosamine and (+)-N-formyltortuosamine

  摘要：

  Three procedures for the transformation of achiral 1-(3,4-dimethoxyphenyl)cyclohexene into enantiomerically pure 2-(3,4-dimethoxyphenyl)cyclohex-2-en-1-ol have been established at first. Utilizing the (-)-cyclohexenol thus obtained, the four titled Sceletium alkaloids have been synthesized in the natural enantiomeric forms. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01689-x

文献信息

• Palladium-catalyzed enantioselective synthesis of cyclohexene derivatives via kinetic resolution
  作者：Toyoki Nishimata、Kentaro Yamaguchi、Miwako Mori

  DOI：10.1016/s0040-4039(99)01079-5

  日期：1999.7

  Reaction of (+/-)-methyl 2-arylcyclohexenyl carbonate with tosyl amide in the presence of a catalytic amount of Pd(2)dba-CHCl3 and (S)-BINAPO produced 2-arylcyclohexenyl tosyl amide with a high ee along with the starting material with a high ee. The reaction involved two processes, and (+)- and (-)-methy] 2-arylcyclohexenyl carbonate gave the same (pi-allyl)palladium complex with a chiral ligand, which gave 2-arylcyclohexenyl tosyl amide with a high ee by enantioselective substitution. The intermediary (pi-allyl)palladium complex was synthesized, and the results of X-ray crystallography are shown. (C) 1999 Elsevier Science Ltd. All rights reserved.