5-<<-2-<1-(benzenesulfonyl)indolyl>>methylidene>-2,2-dimethyl-1,3-dioxane-4,6-dione | 143618-90-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-<<-2-<1-(benzenesulfonyl)indolyl>>methylidene>-2,2-dimethyl-1,3-dioxane-4,6-dione
• 英文别名: 5-[[1-(Benzenesulfonyl)indol-2-yl]methylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione
• CAS: 143618-90-0
• 化学式: C₂₁H₁₇NO₆S
• 分子量: 411.435
• InChiKey: SSHWPAMAQFUQRB-UHFFFAOYSA-N

物化性质

• 沸点：
  723.2±70.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  100
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-<<-2-<1-(benzenesulfonyl)indolyl>>methylidene>-2,2-dimethyl-1,3-dioxane-4,6-dione 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 51.67h， 生成 1-甲基-5H-吡啶并(4,3-b)吲哚-3-羧酸
  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：

  N-苯磺酸吲哚 、 5-乙氧基甲烯基-2,2-二甲基-1,3-二氧六环-4,6-二酮 在 lithium diisopropyl amide 作用下， 生成 5-<<-2-<1-(benzenesulfonyl)indolyl>>methylidene>-2,2-dimethyl-1,3-dioxane-4,6-dione
  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 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.