methyl 1,4-dimethyl-5H-pyrido<4,3-b>indole-3-carboxylate | 128257-25-0

• 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: methyl 1,4-dimethyl-5H-pyrido<4,3-b>indole-3-carboxylate
• 英文别名: methyl 1,4-dimethyl-5H-pyrido[4,3-b]indole-3-carboxylate
• CAS: 128257-25-0
• 化学式: C₁₅H₁₄N₂O₂
• 分子量: 254.288
• InChiKey: WQIFCEYWDAYAEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  55
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 1,4-dimethyl-5H-pyrido<4,3-b>indole-3-carboxylate 在 sodium hydroxide 、 二苯基膦叠氮化物 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 1.5h， 生成 t-Boc-Trp-P-1
  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
• 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 49.17h， 生成 methyl 1,4-dimethyl-5H-pyrido<4,3-b>indole-3-carboxylate
  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

• 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：——
• HIBINO, SATOSHI;SUGINO, EIICHI;OGURA, NAOKI;SHINTANI, YOHKO;SATO, KOHICHI, HETEROCYCLES, 30,(1990) N, C. 271-273
  作者：HIBINO, SATOSHI、SUGINO, EIICHI、OGURA, NAOKI、SHINTANI, YOHKO、SATO, KOHICHI

  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.