t-Boc-Trp-P-2 | 143618-98-8

• 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: t-Boc-Trp-P-2
• 英文别名: tert-butyl N-(1-methyl-5H-pyrido[4,3-b]indol-3-yl)carbamate
• CAS: 143618-98-8
• 化学式: C₁₇H₁₉N₃O₂
• 分子量: 297.357
• InChiKey: DBVPECVRRFTMHS-UHFFFAOYSA-N

物化性质

• 沸点：
  453.1±45.0 °C(Predicted)
• 密度：
  1.268±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  67
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  t-Boc-Trp-P-2 在 溶剂黄146 作用下， 以 水 为溶剂， 反应 1.0h， 以81%的产率得到3-氨基-1-甲基-5H-吡啶[4,3-b]吲哚
  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：

  5-<<-2-<1-(benzenesulfonyl)indolyl>>methylidene>-2,2-dimethyl-1,3-dioxane-4,6-dione 在 sodium hydroxide 、 PPA 、 二苯基膦叠氮化物 、 盐酸羟胺 、 sodium acetate 、 溶剂黄146 、 三乙胺 作用下， 以 甲醇 、 乙醚 、 乙醇 、 氯仿 、 乙腈 、 xylene 为溶剂， 反应 52.17h， 生成 t-Boc-Trp-P-2
  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

• Iminophosphorane-mediated synthesis of the genotoxic heterocyclic amine Trp-P-2.
  作者：Pedro Molina、Pedro Almendros、Pilar M. Fresneda

  DOI：10.1016/s0040-4039(00)60661-5

  日期：1993.9

  A new eight-step synthesis of the genotoxic amine Trp-P-2 in an overall yield of 14.4% is described. The key step, formation of the γ-carboline ring, involves a tandem aza Wittig/electrocyclic ring closure process.

  描述了一种新的八步合成遗传毒性胺Trp-P-2的方法，总收率为14.4％。关键步骤是形成γ-咔啉环，这涉及串联氮杂Wittig /电环闭合过程。
• 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.