(+/-)-(3aS,9bS)-2,3,3a,4,5,9b-hexahydro-5-(4-toluenesulfonyl)-1H-pyrrolo[3,2-c]quinoline

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (+/-)-(3aS,9bS)-2,3,3a,4,5,9b-hexahydro-5-(4-toluenesulfonyl)-1H-pyrrolo[3,2-c]quinoline
• 英文别名: (3aS,9bS)-5-(4-methylphenyl)sulfonyl-1,2,3,3a,4,9b-hexahydropyrrolo[3,2-c]quinoline
• 化学式: C₁₈H₂₀N₂O₂S
• 分子量: 328.435
• InChiKey: UNXCFDIFEMNNKE-KSSFIOAISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  57.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙酰氯 、 (+/-)-(3aS,9bS)-2,3,3a,4,5,9b-hexahydro-5-(4-toluenesulfonyl)-1H-pyrrolo[3,2-c]quinoline 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 cis-1-[2,3,3a,4,5,9b-hexahydro-5-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[3,2-c]quinolin-1-yl]ethanone
  参考文献：
  名称：

  A formal synthesis of martinelline via a combination of two types of radical reactions

  摘要：

  A formal synthesis of martinelline has been accomplished via two types of radical reactions as the key steps. These are the radical addition-cyclization-elimination of an oxime ether carrying an unsaturated ester and a C-C bond formation through a radical 1.5-hydrogen atom translocation. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.02.153
• 作为产物：
  描述：

  2-氨基苯甲酸乙酯 在 palladium on activated charcoal lithium aluminium tetrahydride 、 MnO₂ on activated carbon 、 氢气 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 生成 (+/-)-(3aS,9bS)-2,3,3a,4,5,9b-hexahydro-5-(4-toluenesulfonyl)-1H-pyrrolo[3,2-c]quinoline
  参考文献：
  名称：

  An approach to the pyrroloquinoline core of martinelline and martinellic acid

  摘要：

  An expedient method for the assembly of the pyrroloquinoline skeleton found in the martinelline alkaloids using a [3+2] cycloaddition of an azomethine ylide and an alkene has been developed. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00150-1

文献信息

• Development of radical addition–cyclization–elimination reaction of oxime ether and its application to formal synthesis of (±)-martinelline
  作者：Okiko Miyata、Atsushi Shirai、Shintaro Yoshino、Toshiki Nakabayashi、Yoshifumi Takeda、Toshiko Kiguchi、Daisuke Fukumoto、Masafumi Ueda、Takeaki Naito

  DOI：10.1016/j.tet.2007.07.007

  日期：2007.10

  Radical addition–cyclization–elimination (RACE) reaction of oxime ether carrying unsaturated ester provides a novel method for the construction of pyrroloquinoline. Treatment of oxime ethers with Bu3SnH and AIBN gave N-norpyrroloquinoline as a major product, which was also obtained by the radical reaction of the corresponding hydrazone and imine. The radical reaction of aldehyde and ketone carrying

  带有不饱和酯的肟醚的自由基加成-环化-消除（RACE）反应为吡咯并喹啉的构建提供了一种新方法。用Bu 3 SnH和AIBN处理肟醚，得到N-正吡咯并喹啉为主要产物，其也通过相应的hydr和亚胺的自由基反应获得。醛和酮携带的不饱和酯的自由基反应立体选择性地进行，得到顺式-呋喃喹啉和顺式-羟基酯。还研究了通过使用Bu 3 SnNMe 2，Bu 3 SnD和/或D 2 O中的每一种进行的RACE反应，以提出通向N的反应途径。-去吡咯并喹啉。此外，RACE反应的合成效用通过制备用于合成（±）-martinelline的关键中间体而得到证明。
• An approach to the pyrroloquinoline core of martinelline and martinellic acid
  作者：Carl J. Lovely、Hossen Mahmud

  DOI：10.1016/s0040-4039(99)00150-1

  日期：1999.3

  An expedient method for the assembly of the pyrroloquinoline skeleton found in the martinelline alkaloids using a [3+2] cycloaddition of an azomethine ylide and an alkene has been developed. (C) 1999 Elsevier Science Ltd. All rights reserved.
• An intramolecular azomethine ylide–alkene cycloaddition approach to pyrrolo[3,2-c]quinolines-synthesis of a C2-truncated martinelline model
  作者：Hossen Mahmud、Carl J Lovely、H.V Rasika Dias

  DOI：10.1016/s0040-4020(01)00315-5

  日期：2001.5

  The hexahydropyrrolo[3,2-c]quinoline core found in the Martinella alkaloids was constructed through an intramolecular [3+2] azomethine ylide-alkene cycloaddition. Some chemical manipulations of the tricycle are reported. (C) 2001 Elsevier Science Ltd. AU rights reserved.
• A formal synthesis of martinelline via a combination of two types of radical reactions
  作者：Yoshifumi Takeda、Toshiki Nakabayashi、Atsushi Shirai、Daisuke Fukumoto、Toshiko Kiguchi、Takeaki Naito

  DOI：10.1016/j.tetlet.2004.02.153

  日期：2004.4

  A formal synthesis of martinelline has been accomplished via two types of radical reactions as the key steps. These are the radical addition-cyclization-elimination of an oxime ether carrying an unsaturated ester and a C-C bond formation through a radical 1.5-hydrogen atom translocation. (C) 2004 Elsevier Ltd. All rights reserved.