2-[(8R)-8-(3,4-dimethoxyphenyl)-6-[(Z)-2-(1,3-dioxolan-2-yl)ethenyl]-1,4-dioxaspiro[4.5]dec-6-en-8-yl]-N-methylethanamine | 216005-98-0

• 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-[(8R)-8-(3,4-dimethoxyphenyl)-6-[(Z)-2-(1,3-dioxolan-2-yl)ethenyl]-1,4-dioxaspiro[4.5]dec-6-en-8-yl]-N-methylethanamine
• CAS: 216005-98-0
• 化学式: C₂₄H₃₃NO₆
• 分子量: 431.529
• InChiKey: RIFSSJRENLVFQT-BLAQYMCESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  67.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-[(8R)-8-(3,4-dimethoxyphenyl)-6-[(Z)-2-(1,3-dioxolan-2-yl)ethenyl]-1,4-dioxaspiro[4.5]dec-6-en-8-yl]-N-methylethanamine 在 ammonium acetate 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 24.0h， 生成 3a-(3,4-dimethoxy-phenyl)-1-methyl-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[2,3-f]quinoline
  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 在 bis-triphenylphosphine-palladium(II) chloride 、 Lindlar's catalyst 、 copper(l) iodide 3,5-二甲基吡唑 、 chromium(VI) oxide 、 氢氧化钾 、 氢气 、 碘 、 对甲苯磺酸 、 二异丙胺 作用下， 以 四氢呋喃 、 吡啶 、 四氯化碳 、 乙醇 、 二氯甲烷 、 乙酸乙酯 、 苯 为溶剂， 反应 79.17h， 生成 2-[(8R)-8-(3,4-dimethoxyphenyl)-6-[(Z)-2-(1,3-dioxolan-2-yl)ethenyl]-1,4-dioxaspiro[4.5]dec-6-en-8-yl]-N-methylethanamine
  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.