1,4-dimethyl-5H-pyrido<4,3-b>indole-3-carboxylic acid | 96286-20-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1,4-dimethyl-5H-pyrido<4,3-b>indole-3-carboxylic acid
• 英文别名: 1,4-Dimethyl-5h-pyrido[4,3-b]indole-3-carboxylic acid
• CAS: 96286-20-3
• 化学式: C₁₄H₁₂N₂O₂
• 分子量: 240.261
• InChiKey: STAOMMZXWLIDRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  66
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,4-dimethyl-5H-pyrido<4,3-b>indole-3-carboxylic acid 在 叠氮磷酸二苯酯 、 三乙胺 作用下， 生成 t-Boc-Trp-P-1
  参考文献：
  名称：

  The Firat Synthesis of Mutagenic Trp-P-1 via the Electrocyclic Reaction of 1-Azahexa-1,3,5-triene System

  摘要：

  DOI：

  10.3987/com-89-s29
• 作为产物：
  描述：

  phenyl 3-[1-(benzenesulfonyl)indol-2-yl]but-2-enoate 在 sodium hydroxide 、 PPA 、 盐酸羟胺 、 sodium acetate 、 溶剂黄146 作用下， 以 甲醇 、 乙醚 、 乙醇 、 氯仿 、 乙腈 、 xylene 为溶剂， 反应 50.17h， 生成 1,4-dimethyl-5H-pyrido<4,3-b>indole-3-carboxylic acid
  参考文献：
  名称：

  Synthesis of genotoxic heterocyclic amines Trp-P-1 and Trp-P-2

  摘要：

  Trp-P-1 (1a) and Trp-P-2 (1b) possessing a pyrido[4,3-b]indole system have been newly synthesized. The key reaction step in the synthetic sequence has been the thermal electrocyclic reaction of the 1-azahexa-1,3,5-triene system 3 involving the indole [b] bond derived from 2-vinylindoles 4. 2-Vinylindole 4a has been derived from N-(benzenesulfonyl)indole (5) in a four-step sequence. 2-Vinylindole 4b has been synthesized by two routes using either ethoxymethylidene Meldrum's acid (6b) or diethyl ethoxymethylidenemalonate (10) as Michael acceptors to the 2-lithio-N-(benzenesulfonyl)indole.

  DOI：

  10.1021/jo00048a026

文献信息

• Synthesis of 3-Amino-5<i>H</i>-pyrido[4,3-<i>b</i>]indoles, Carcinogenic γ-Carbolines
  作者：Hiroshi Akimoto、Akiyoshi Kawai、Hiroaki Nomura

  DOI：10.1246/bcsj.58.123

  日期：1985.1

  ne to synthesize 1 and the condensation of 3-acetylindole-2- acetonitrile with ammonia to synthesize 2. The structures of γ-carbolines 1 and 2 were unambiguously established by comparing samples of each synthesized by the two different routes. A selective and one-step synthesis of ethyl 2-acetamido-3-(2-indolyl)alkanoates was newly exploited starting from diethyl acetamidomalonate and quaternary ammonium

  致癌性γ-咔啉3-氨基-1,4-二甲基-5H-吡啶并[4,3-b]吲哚(1)和3-氨基-1-甲基-5H-吡啶并[4,3-b]吲哚( 2) 通过以下程序有效合成。关键方法涉及酸催化 2-乙酰氨基-3-(2-吲哚基) 链烷酸环化为 1,2-二氢-γ-咔啉。随后脱氢为 γ-咔啉羧酸酯，酯基转化为羧基，最后通过 Curtius 重排转化为氨基。替代方法包括 4-(1-苯并三唑基)-3,6-二甲基-2-吡啶胺热解合成 1 和 3-乙酰吲哚-2-乙腈与氨缩合合成 2。 γ-咔啉的结构 1和 2 是通过比较两种不同途径合成的每种样品而明确建立的。
• AKIMOTO, HIROSHI;KAWAI, AKIYOSHI;NOMURA, HIROAKI, BULL. CEM. SOC. JAP., 1985, 58, N 1, 123-130
  作者：AKIMOTO, HIROSHI、KAWAI, AKIYOSHI、NOMURA, HIROAKI

  DOI：——

  日期：——
• Synthesis of genotoxic heterocyclic amines Trp-P-1 and Trp-P-2
  作者：Satoshi Hibino、Eiichi Sugino、Takeshi Kuwada、Naoki Ogura、Kohichi Sato、Tominari Choshi

  DOI：10.1021/jo00048a026

  日期：1992.10

  Trp-P-1 (1a) and Trp-P-2 (1b) possessing a pyrido[4,3-b]indole system have been newly synthesized. The key reaction step in the synthetic sequence has been the thermal electrocyclic reaction of the 1-azahexa-1,3,5-triene system 3 involving the indole [b] bond derived from 2-vinylindoles 4. 2-Vinylindole 4a has been derived from N-(benzenesulfonyl)indole (5) in a four-step sequence. 2-Vinylindole 4b has been synthesized by two routes using either ethoxymethylidene Meldrum's acid (6b) or diethyl ethoxymethylidenemalonate (10) as Michael acceptors to the 2-lithio-N-(benzenesulfonyl)indole.
• The Firat Synthesis of Mutagenic Trp-P-1 via the Electrocyclic Reaction of 1-Azahexa-1,3,5-triene System
  作者：Satoshi Hibino、Eiichi Sugino、Naoki Sgura、Yohko Shintani、Kohichi Sato

  DOI：10.3987/com-89-s29

  日期：——