(5S,10bS)-Se-methyl 8,9-dimethoxy-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline-5-carboselenoate | 1269617-15-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: (5S,10bS)-Se-methyl 8,9-dimethoxy-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline-5-carboselenoate
• 英文别名: Se-methyl (5S,10bS)-8,9-dimethoxy-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline-5-carboselenoate
• CAS: 1269617-15-3
• 化学式: C₁₆H₂₁NO₃Se
• 分子量: 354.308
• InChiKey: BMGBLKCKJAGRGV-STQMWFEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.04
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5S,10bS)-Se-methyl 8,9-dimethoxy-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline-5-carboselenoate 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 3.0h， 以55%的产率得到(S)-crispine A
  参考文献：
  名称：

  Concise Enantiospecific, Stereoselective Syntheses of (+)-Crispine A and Its (−)-Antipode

  摘要：

  An enantiospecific and stereoselective total synthesis of the natural product (+)-crispine A has been demonstrated employing a Pictet-Spengler bis-cyclization reaction between commercially available (R)-(-)-methyl 2-amino-3-(3,4-dimethoxyphenyl)propanoate and 4-chloro-1,1-dimethoxybutane to preferentially provide the cis tricyclic adduct. Decarboxylation by a convenient two-step protocol provided the enantiopure natural product in three steps with an overall isolated yield of 32% from the amino acid. The unnatural antipode (-)-crispine A was similarly prepared in three steps from the commercially available (S)-(+)-amino acid.

  DOI：

  10.1021/jo102112k
• 作为产物：
  描述：

  盐酸左旋多巴甲酯 在 potassium carbonate 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 20.0h， 生成 (5S,10bS)-Se-methyl 8,9-dimethoxy-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline-5-carboselenoate
  参考文献：
  名称：

  Concise Enantiospecific, Stereoselective Syntheses of (+)-Crispine A and Its (−)-Antipode

  摘要：

  An enantiospecific and stereoselective total synthesis of the natural product (+)-crispine A has been demonstrated employing a Pictet-Spengler bis-cyclization reaction between commercially available (R)-(-)-methyl 2-amino-3-(3,4-dimethoxyphenyl)propanoate and 4-chloro-1,1-dimethoxybutane to preferentially provide the cis tricyclic adduct. Decarboxylation by a convenient two-step protocol provided the enantiopure natural product in three steps with an overall isolated yield of 32% from the amino acid. The unnatural antipode (-)-crispine A was similarly prepared in three steps from the commercially available (S)-(+)-amino acid.

  DOI：

  10.1021/jo102112k

文献信息

• Concise Enantiospecific, Stereoselective Syntheses of (+)-Crispine A and Its (−)-Antipode
  作者：Mahender Gurram、Balázs Gyimóthy、Ruifang Wang、Sang Q. Lam、Feryan Ahmed、R. Jason Herr

  DOI：10.1021/jo102112k

  日期：2011.3.18

  An enantiospecific and stereoselective total synthesis of the natural product (+)-crispine A has been demonstrated employing a Pictet-Spengler bis-cyclization reaction between commercially available (R)-(-)-methyl 2-amino-3-(3,4-dimethoxyphenyl)propanoate and 4-chloro-1,1-dimethoxybutane to preferentially provide the cis tricyclic adduct. Decarboxylation by a convenient two-step protocol provided the enantiopure natural product in three steps with an overall isolated yield of 32% from the amino acid. The unnatural antipode (-)-crispine A was similarly prepared in three steps from the commercially available (S)-(+)-amino acid.