(5R,10bR)-methyl 8,9-dimethoxy-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline-5-carboxylate | 1269617-20-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (5R,10bR)-methyl 8,9-dimethoxy-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline-5-carboxylate
• 英文别名: methyl (5R,10bR)-8,9-dimethoxy-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline-5-carboxylate
• CAS: 1269617-20-0
• 化学式: C₁₆H₂₁NO₄
• 分子量: 291.347
• InChiKey: PDHIZYJABKYKJN-CHWSQXEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 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：
  48
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (5R,10bR)-methyl 8,9-dimethoxy-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline-5-carboxylate 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 二氯甲烷 、 甲苯 、 苯 为溶剂， 反应 4.0h， 生成 (R)-(+)-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：

  2-(3-氯丙基)-1,3-二噁戊环 、 2-amino-3-(3,4-dimethoxybenz-1-yl)propanoic acid methyl ester 以63%的产率得到
  参考文献：
  名称：

  Short stereoselective synthesis of (+)-crispine A via an N-sulfinyl Pictet–Spengler reaction

  摘要：

  We report the highly stereoselective synthesis of (R)-(+)-crispine A from the (R)-N-sulfinyl amine 1 by using a one-pot process involving the Pictet-Spengler reaction with 4-chlorobutanal, removal of the sulfinyl group by protonolysis of the N-S bond and in situ cyclization, with a 55% overall yield. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.01.121

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.
• Short stereoselective synthesis of (+)-crispine A via an N-sulfinyl Pictet–Spengler reaction
  作者：Rubén Sánchez-Obregón、Benjamín Ortiz、Virginia M. Mastranzo、Francisco Yuste、José Luis García Ruano

  DOI：10.1016/j.tetlet.2013.01.121

  日期：2013.4

  We report the highly stereoselective synthesis of (R)-(+)-crispine A from the (R)-N-sulfinyl amine 1 by using a one-pot process involving the Pictet-Spengler reaction with 4-chlorobutanal, removal of the sulfinyl group by protonolysis of the N-S bond and in situ cyclization, with a 55% overall yield. (C) 2013 Elsevier Ltd. All rights reserved.