2-amino-3-(4-chlorobenzoyl)indolizine-1-carbonitrile | 353262-87-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-amino-3-(4-chlorobenzoyl)indolizine-1-carbonitrile
• 英文别名: 2-amino-3-(p-chlorobenzoyl)indolizine-1-carbonitrile
• CAS: 353262-87-0
• 化学式: C₁₆H₁₀ClN₃O
• 分子量: 295.728
• InChiKey: ASPPEPBAQYYVSC-UHFFFAOYSA-N

物化性质

• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  对甲基苯乙酮 、 2-amino-3-(4-chlorobenzoyl)indolizine-1-carbonitrile 在 potassium tert-butylate 作用下， 反应 6.0h， 以27%的产率得到4-(p-chlorophenyl)-2-(p-methylphenyl)pyrido[2,3-b]indolizine-10-carbonitrile
  参考文献：
  名称：

  Preparation of New Nitrogen-bridged Heterocycles. 64. A Smooth Formation of 2,4-Diarylpyrido[2,3-b]indolizine-10-carbonitrile Derivatives

  摘要：

  The syntheses of the title compounds from the reactions of 2-amino-3-(arylcarbonyl)indolizine-1-carbonitriles with various acetophenones in the presence of strong base were investigated. When the reactions were carried out between 2-aminoindolizines and 1.2-equimolar amounts of acetophenones, the yields for the target molecules were low or very low. However, when a large excess of acetophenones were used without any solvent or in as small as amount of solvent as possible, their yields were considerably improved. The smooth hydrolysis of the 10-cyano group to the carbamoyl one was also observed.

  DOI：

  10.3987/com-08-s(f)44
• 作为产物：
  描述：

  2-chloro-1-[(4-chlorobenzoyl)methyl]pyridinium bromide 在 三乙胺 作用下， 以 乙醇 、 正丁醇 为溶剂， 反应 4.0h， 生成 2-amino-3-(4-chlorobenzoyl)indolizine-1-carbonitrile
  参考文献：
  名称：

  Kröhnke–Mukaiyama盐与丙二腈二聚体的反应级联合成吡啶并[3,2- a ]吲哚嗪

  摘要：

  通过使N -RC（O）CH 2 -2-氯吡啶鎓溴化物与2-amino-1,1反应，已经获得了一种高效合成高度官能化的2-氨基吲哚并吡啶并[3,2- a ] indolizines的有效方法。在Et 3 N存在下，3-3-三氰基丙烯。在Et 3 N存在下，N-烯丙基-2-氯吡啶溴与2-氨基-1,1,3-三氰基丙烯的反应得到3- [1-1-烯丙基吡啶- 2（1个Н） -亚基] -2-氨基丙-1-烯-1,1,3- tricarbonitrile，这可能被环化，得到[2-氨基- （2-氨基-3- vinylindolizin -1-基）亚甲基KOH-DMF处理后]]丙二腈。

  DOI：

  10.1016/j.tetlet.2014.10.046

文献信息

• ——
  作者：G. E. Khoroshilov

  DOI：10.1023/a:1013240002478

  日期：——
• Regioselective reaction of 2-amino-3-aroyl-1-cyanoindolizines with formamide
  作者：G. E. Khoroshilov、I. V. Demchak、M. V. Emelyanova

  DOI：10.1007/s10593-007-0019-8

  日期：2007.1
• Cascade synthesis of pyrido[3,2-a]indolizines by reaction of Kröhnke–Mukaiyama salts with malononitrile dimer
  作者：Natalia M. Tverdokhleb、Gennadiy E. Khoroshilov、Victor V. Dotsenko

  DOI：10.1016/j.tetlet.2014.10.046

  日期：2014.11

  An efficient protocol for the synthesis of highly functionalized 2-aminoindolizines and pyrido[3,2-a]indolizines has been achieved via the reaction of N-RC(O)CH2-2-chloropyridinium bromides with 2-amino-1,1,3-tricyanopropene in the presence of Et3N. The reaction of N-allyl-2-chloropyridinium bromide with 2-amino-1,1,3-tricyanopropene in the presence of Et3N gives 3-[1-allylpyridin-2(1Н)-ylidene]-2-aminoprop-1-ene-1

  通过使N -RC（O）CH 2 -2-氯吡啶鎓溴化物与2-amino-1,1反应，已经获得了一种高效合成高度官能化的2-氨基吲哚并吡啶并[3,2- a ] indolizines的有效方法。在Et 3 N存在下，3-3-三氰基丙烯。在Et 3 N存在下，N-烯丙基-2-氯吡啶溴与2-氨基-1,1,3-三氰基丙烯的反应得到3- [1-1-烯丙基吡啶- 2（1个Н） -亚基] -2-氨基丙-1-烯-1,1,3- tricarbonitrile，这可能被环化，得到[2-氨基- （2-氨基-3- vinylindolizin -1-基）亚甲基KOH-DMF处理后]]丙二腈。
• Preparation of New Nitrogen-bridged Heterocycles. 64. A Smooth Formation of 2,4-Diarylpyrido[2,3-b]indolizine-10-carbonitrile Derivatives
  作者：Akikazu Kakehi、Hiroyuki Suga、Shuichi Sato

  DOI：10.3987/com-08-s(f)44

  日期：——

  The syntheses of the title compounds from the reactions of 2-amino-3-(arylcarbonyl)indolizine-1-carbonitriles with various acetophenones in the presence of strong base were investigated. When the reactions were carried out between 2-aminoindolizines and 1.2-equimolar amounts of acetophenones, the yields for the target molecules were low or very low. However, when a large excess of acetophenones were used without any solvent or in as small as amount of solvent as possible, their yields were considerably improved. The smooth hydrolysis of the 10-cyano group to the carbamoyl one was also observed.