乙基吡咯并[1,2-a]喹啉-2-羧酸酯 | 76577-82-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 乙基吡咯并[1,2-a]喹啉-2-羧酸酯
• 英文名称: ethyl pyrrolo<1,2-a>quinoline-2-carboxylate
• 英文别名: Ethyl pyrrolo[1,2-a]quinoline-2-carboxylate
• CAS: 76577-82-7
• 化学式: C₁₅H₁₃NO₂
• 分子量: 239.274
• InChiKey: QJEYZIIXKJLBIY-UHFFFAOYSA-N

物化性质

• 熔点：
  77-78 °C
• 沸点：
  254.9±23.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  乙基吡咯并[1,2-a]喹啉-2-羧酸酯 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以82%的产率得到pyrrolo<1,2-a>quinoline-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and oral antiallergic activity of carboxylic acids derived from imidazo[2,1-c][1,4]benzoxazines, imidazo[1,2-a]quinolines, imidazo[1,2-a]quinoxalines, imidazo[1,2-a]quinoxalinones, pyrrolo[1,2-a]quinoxalinones, pyrrolo[2,3-a]quinoxalinones, and imidazo[2,1-b]benzothiazoles

  摘要：

  4H-Imidazo[2,1-c][1,4]benzoxazine-2-carboxylic acid (3) was found to possess potent activity in the IgE-induced rat passive cutaneous anaphylaxis model which may be predictive of clinical antiallergic activity. Compared to disodium cromoglycate (DSCG, 1), 3 was less active following iv administration but unlike DSCG showed very significant oral activity. To explore the structural requirements for this activity, a range of tricyclic compounds was prepared and their activities were measured. Individual 2-carboxylic acids derived from imidazo[1,2-a]quinolines, imidazo[1,2-a]quinoxalines, imidazo[1,2-a]quinoxalinones, pyrrolo[1,2-a]quinoxalinones, pyrrolo[2,3-a]quinoxalinones, and imidazo[2,1-b]benzothiazoles showed iv activities up to 10(3) times as potent as DSCG and many of them showed significant oral activity. From these, imidazo[1,2-a]quinoxaline-2-carboxylic acid 114 has been chosen for further development.

  DOI：

  10.1021/jm00401a009
• 作为产物：
  描述：

  ethyl 3-hydroxy-2-methylene-3-(quinolin-2-yl)propionate 在 吡啶 、 乙酰氯 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 乙基吡咯并[1,2-a]喹啉-2-羧酸酯
  参考文献：
  名称：

  通过布朗斯台德酸催化的氮杂-弗里德尔-克来福特反应，热力学控制的中氮茚与 3-羟基异二氢吲哚酮的区域选择性 C1 官能化

  摘要：

  建立了布朗斯台德酸催化的氮杂吲嗪与 3-羟基异吲哚啉酮的氮杂-弗里德尔-克来福特反应，该反应构建了具有四取代立构中心的异吲哚啉酮衍生物，具有良好至高的产率和对映选择性。值得注意的是，该策略提供了具有优异区域选择性的中氮茚 C1 功能化的新途径。此外，这种有趣的 C1 区域选择性转变是在热力学控制下诱导的。

  DOI：

  10.1021/acs.joc.3c02522

文献信息

• A mild preparation of substituted indolizines and indole from simple aromatic precursors using (trimethylsilyl)diazomethane
  作者：Liusheng Zhu、Marc Vimolratana、Sean P. Brown、Julio C. Medina

  DOI：10.1016/j.tetlet.2008.01.067

  日期：2008.3

  A mild and convenient synthesis of substituted indolizines from readily available 2-(pyridin-2-yl)acetyl derivatives using (trimethylsilyl)diazomethane is described. The extension of this methodology to the synthesis of indole from 2-aminobenzaldehyde is also reported.

  描述了使用（三甲基甲硅烷基）重氮甲烷由容易获得的2-（吡啶-2-基）乙酰基衍生物温和方便地合成取代的吲哚嗪的方法。还报道了该方法的扩展到由2-氨基苯甲醛合成吲哚。
• AGER, IAN R.;BARNES, ALAN C.;DANSWAN, GEOFFREY W.;HAIRSINE, PETER W.;KAY,+, J. MED. CHEM., 31,(1988) N 6, 1098-1115
  作者：AGER, IAN R.、BARNES, ALAN C.、DANSWAN, GEOFFREY W.、HAIRSINE, PETER W.、KAY,+

  DOI：——

  日期：——
• Synthesis and oral antiallergic activity of carboxylic acids derived from imidazo[2,1-c][1,4]benzoxazines, imidazo[1,2-a]quinolines, imidazo[1,2-a]quinoxalines, imidazo[1,2-a]quinoxalinones, pyrrolo[1,2-a]quinoxalinones, pyrrolo[2,3-a]quinoxalinones, and imidazo[2,1-b]benzothiazoles
  作者：Ian R. Ager、Alan C. Barnes、Geoffrey W. Danswan、Peter W. Hairsine、David P. Kay、Peter D. Kennewell、Saroop S. Matharu、Peter Miller、Peter Robson

  DOI：10.1021/jm00401a009

  日期：1988.6

  4H-Imidazo[2,1-c][1,4]benzoxazine-2-carboxylic acid (3) was found to possess potent activity in the IgE-induced rat passive cutaneous anaphylaxis model which may be predictive of clinical antiallergic activity. Compared to disodium cromoglycate (DSCG, 1), 3 was less active following iv administration but unlike DSCG showed very significant oral activity. To explore the structural requirements for this activity, a range of tricyclic compounds was prepared and their activities were measured. Individual 2-carboxylic acids derived from imidazo[1,2-a]quinolines, imidazo[1,2-a]quinoxalines, imidazo[1,2-a]quinoxalinones, pyrrolo[1,2-a]quinoxalinones, pyrrolo[2,3-a]quinoxalinones, and imidazo[2,1-b]benzothiazoles showed iv activities up to 10(3) times as potent as DSCG and many of them showed significant oral activity. From these, imidazo[1,2-a]quinoxaline-2-carboxylic acid 114 has been chosen for further development.
• Thermodynamic Controlled Regioselective C1-Functionalization of Indolizines with 3-Hydroxyisoindolinones via Brønsted Acid Catalyzed aza-Friedel–Crafts Reaction
  作者：Zhiming Zhu、Qianling Wu、Xiaoxiao Song、Qijian Ni

  DOI：10.1021/acs.joc.3c02522

  日期：2024.2.16

  A Brønsted acid catalyzed aza-Friedel–Crafts reaction of indolizines with 3-hydroxyisoindolinones has been established, which constructs isoindolinone derivatives bearing a tetrasubstituted stereocenter in good to high yields and enantioselectivities. Notably, this strategy provides a new access to C1-functionalization of indolizines with excellent regioselectivities. Moreover, this intriguing C1-regioselective

  建立了布朗斯台德酸催化的氮杂吲嗪与 3-羟基异吲哚啉酮的氮杂-弗里德尔-克来福特反应，该反应构建了具有四取代立构中心的异吲哚啉酮衍生物，具有良好至高的产率和对映选择性。值得注意的是，该策略提供了具有优异区域选择性的中氮茚 C1 功能化的新途径。此外，这种有趣的 C1 区域选择性转变是在热力学控制下诱导的。