(+)-(3aS,7aS)-3a-(3,4-dimethoxyphenyl)-1-methyl-6-[(2,2-dimethyl-3-hydroxypropyl)oxy]-7-formyl-2,3,3a,4,5,7a-hexahydro-6H-indole | 187850-45-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (+)-(3aS,7aS)-3a-(3,4-dimethoxyphenyl)-1-methyl-6-[(2,2-dimethyl-3-hydroxypropyl)oxy]-7-formyl-2,3,3a,4,5,7a-hexahydro-6H-indole
• 英文别名: (3aS,7aR)-3a-(3,4-dimethoxyphenyl)-6-(3-hydroxy-2,2-dimethylpropoxy)-1-methyl-3,4,5,7a-tetrahydro-2H-indole-7-carbaldehyde
• CAS: 187850-45-9
• 化学式: C₂₃H₃₃NO₅
• 分子量: 403.519
• InChiKey: ITJDWESQFFHTNZ-GMAHTHKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  68.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (+)-(3aS,7aS)-3a-(3,4-dimethoxyphenyl)-1-methyl-6-[(2,2-dimethyl-3-hydroxypropyl)oxy]-7-formyl-2,3,3a,4,5,7a-hexahydro-6H-indole 在 sodium hydroxide 、 三氟乙酸 作用下， 生成 松叶菊碱提取物
  参考文献：
  名称：

  Asymmetric Construction of a Quaternary Carbon Center by Tandem [4 + 2]/[3 + 2] Cycloaddition of a Nitroalkene. The Total Synthesis of (−)-Mesembrine

  摘要：

  An efficient, total synthesis of the Sceletium alkaloid (-)-mesembrine is accomplished in seven steps and 19% yield from a functionalized nitroalkene (itself prepared in six steps and 34% yield from ethyl 3-bromopropionate). The construction of the octahydroindole framework of mesembrine features a tandem inter [4 + 2]/intra [3 + 2] cycloaddition of a 2,2-disubstituted 1-nitroalkene and a chiral vinyl ether derived from (1R,2S)-2-(l-methyl-l-phenylethyl)cyclo as the central strategic element. The two stereogenic centers of the natural product, which include a benzylic, quaternary center, were established in 26/1 selectivity in the tandem process.

  DOI：

  10.1021/jo970079z
• 作为产物：
  描述：

  (+)-[(3aS,7R,7aS)-3a-(3,4-dimethoxyphenyl)-6,6-(2,2-dimethylpropylenedioxy)octahydroindol-7-yl]methanol 在 镍 乙基溴化镁 、 氢气 、 1,1'-azodicarbonyl-dipiperidine 、 叔丁醇 作用下， 反应 50.83h， 生成 (+)-(3aS,7aS)-3a-(3,4-dimethoxyphenyl)-1-methyl-6-[(2,2-dimethyl-3-hydroxypropyl)oxy]-7-formyl-2,3,3a,4,5,7a-hexahydro-6H-indole
  参考文献：
  名称：

  Asymmetric Construction of a Quaternary Carbon Center by Tandem [4 + 2]/[3 + 2] Cycloaddition of a Nitroalkene. The Total Synthesis of (−)-Mesembrine

  摘要：

  An efficient, total synthesis of the Sceletium alkaloid (-)-mesembrine is accomplished in seven steps and 19% yield from a functionalized nitroalkene (itself prepared in six steps and 34% yield from ethyl 3-bromopropionate). The construction of the octahydroindole framework of mesembrine features a tandem inter [4 + 2]/intra [3 + 2] cycloaddition of a 2,2-disubstituted 1-nitroalkene and a chiral vinyl ether derived from (1R,2S)-2-(l-methyl-l-phenylethyl)cyclo as the central strategic element. The two stereogenic centers of the natural product, which include a benzylic, quaternary center, were established in 26/1 selectivity in the tandem process.

  DOI：

  10.1021/jo970079z

文献信息

• Asymmetric Construction of a Quaternary Carbon Center by Tandem [4 + 2]/[3 + 2] Cycloaddition of a Nitroalkene. The Total Synthesis of (−)-Mesembrine
  作者：Scott E. Denmark、Lawrence R. Marcin

  DOI：10.1021/jo970079z

  日期：1997.3.1

  An efficient, total synthesis of the Sceletium alkaloid (-)-mesembrine is accomplished in seven steps and 19% yield from a functionalized nitroalkene (itself prepared in six steps and 34% yield from ethyl 3-bromopropionate). The construction of the octahydroindole framework of mesembrine features a tandem inter [4 + 2]/intra [3 + 2] cycloaddition of a 2,2-disubstituted 1-nitroalkene and a chiral vinyl ether derived from (1R,2S)-2-(l-methyl-l-phenylethyl)cyclo as the central strategic element. The two stereogenic centers of the natural product, which include a benzylic, quaternary center, were established in 26/1 selectivity in the tandem process.