methyl N-[2-[(1R)-1-(3,4-dimethoxyphenyl)cyclohex-2-en-1-yl]ethyl]-N-methylcarbamate | 216005-92-4

• 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: methyl N-[2-[(1R)-1-(3,4-dimethoxyphenyl)cyclohex-2-en-1-yl]ethyl]-N-methylcarbamate
• CAS: 216005-92-4
• 化学式: C₁₉H₂₇NO₄
• 分子量: 333.428
• InChiKey: FZYUVOOVJFOYTF-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl N-[2-[(1R)-1-(3,4-dimethoxyphenyl)cyclohex-2-en-1-yl]ethyl]-N-methylcarbamate 在 3,5-二甲基吡唑 、 chromium(VI) oxide 、 氢氧化钾 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 26.0h， 生成 松叶菊碱提取物
  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：

  O-[(1R,2S)-2-(3,4-dimethoxyphenyl)-2-[2-[methoxycarbonyl(methyl)amino]ethyl]cyclohexyl] methylsulfanylmethanethioate 以 various solvent(s) 为溶剂， 反应 18.0h， 以82%的产率得到methyl N-[2-[(1R)-1-(3,4-dimethoxyphenyl)cyclohex-2-en-1-yl]ethyl]-N-methylcarbamate
  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

• Asymmetric synthesis of sceletium alkaloids: (−)-mesembrine, (+)-sceletium A-4, (+)-tortuosamine and (+)-N-formyltortuosamine
  作者：Osamu Yamada、Kunio Ogasawara

  DOI：10.1016/s0040-4039(98)01689-x

  日期：1998.10

  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.