4-chloro-2-(pyrrol-1-yl)benzaldehyde

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 4-chloro-2-(pyrrol-1-yl)benzaldehyde
• 英文别名: 4-Chloro-2-pyrrol-1-ylbenzaldehyde；4-chloro-2-pyrrol-1-ylbenzaldehyde
• 化学式: C₁₁H₈ClNO
• 分子量: 205.644
• InChiKey: ITFORBAOUFSCNI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-chloro-2-(pyrrol-1-yl)benzaldehyde 在 盐酸 、 air 作用下， 以 乙二醇二甲醚 为溶剂， 反应 2.0h， 生成 7-chloro-9H-pyrrolo[1,2-a]indol-9-one
  参考文献：
  名称：

  9-芳氨基和（合成Ž）-9-芳基亚氨基-9- ħ -吡咯并[1,2-一个]吲哚通过2-（吡咯-1-基）苯甲醛反应，与芳基胺

  摘要：

  通过将所得的2-（吡咯-1-基）环合，在氩气下加热2-（吡咯-1-基）苯甲醛和芳基胺的混合物，得到9-芳基氨基-9 H-吡咯并[1,2- a ]吲哚。苯甲二胺中间体。在氧气存在下加热得到（Z）-9-芳基-9 H-吡咯并[1,2- a ]吲哚，将其成功地用盐酸水解，得到吡咯并[1,2 - a ]吲哚-9-ones。 。

  DOI：

  10.1016/j.tet.2007.02.129
• 作为产物：
  描述：

  4-chloro-2-(1H-pyrrol-1-yl)phenylmethanol 在 Celite 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 生成 4-chloro-2-(pyrrol-1-yl)benzaldehyde
  参考文献：
  名称：

  Morita–Baylis–Hillman route to 4H-pyrrolo[1,2-a][1]benzazepine derivatives

  摘要：

  A simple method for synthesizing substituted 4H-pyrrolo[1,2-a][1]benzazepines using acid-assisted cyclization of the Morita-Baylis-Hillman adducts of 2-(1H-pyrrol-1-yl)benzaldehydes with methyl acrylate or methyl vinyl ketone as a key step has been developed. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.04.026

文献信息

• Design, Synthesis, and Biological Evaluation of New 1-(Aryl-1<i>H</i>-pyrrolyl)(phenyl)methyl-1<i>H</i>-imidazole Derivatives as Antiprotozoal Agents
  作者：Francesco Saccoliti、Valentina Noemi Madia、Valeria Tudino、Alessandro De Leo、Luca Pescatori、Antonella Messore、Daniela De Vita、Luigi Scipione、Reto Brun、Marcel Kaiser、Pascal Mäser、Claudia M. Calvet、Gareth K. Jennings、Larissa M. Podust、Giacomo Pepe、Roberto Cirilli、Cristina Faggi、Annalise Di Marco、Maria Rosaria Battista、Vincenzo Summa、Roberta Costi、Roberto Di Santo

  DOI：10.1021/acs.jmedchem.8b01464

  日期：2019.2.14

  We have designed and synthesized a series of new imidazole-based compounds structurally related to an antiprotozoal agent with nanomolar activity which we identified recently. The new analogues possess micromolar activities against Trypanosoma brucei rhodesiense and Leishmania donovani and nanomolar potency against Plasmodium falciparum. Most of the analogues displayed IC50 within the low nanomolar range against Trypanosoma cruzi, with very high selectivity toward the parasite. Discussion of structure activity relationships and in vitro biological data for the new compounds are provided against a number of different protozoa. The mechanism of action for the most potent derivatives (Si, 6a-c, and 8b) was assessed by a target-based assay using recombinant T. cruzi GYPS1. Bioavailability and efficacy of selected hits were assessed in a T. cruzi mouse model, where 6a and 6b reduced parasitemia in animals >99% following intraperitoneal administration of 25 mg/kg/day dose for 4 consecutive days.
• A new method for the synthesis of pyrrolo[1,2-a]quinolines based on boron trifluoride-mediated cyclization of 1-(2-oxiranylphenyl)pyrroles
  作者：K KOBAYASHI、A TAKANOHASHI、Y HIMEI、T SANO、S FUKAMACHI、O MORIKAWA、H KONISHI

  DOI：10.1016/s0385-5414(07)81207-x

  日期：2007.12.1

  A simple synthesis of pyrrolo[1,2-a]quinolines carrying no substituent at all of the 1- to 5-positions based on boron trifluoride-mediated cyclization of 1-(2-oxiranylphenyl)pyrroles, which can be easily prepared from 2-(pyrrol-1-yl)benzaldehydes, is described.
• Morita–Baylis–Hillman route to 4H-pyrrolo[1,2-a][1]benzazepine derivatives
  作者：Sun Pil Park、Young Seok Song、Kee-Jung Lee

  DOI：10.1016/j.tet.2009.04.026

  日期：2009.6

  A simple method for synthesizing substituted 4H-pyrrolo[1,2-a][1]benzazepines using acid-assisted cyclization of the Morita-Baylis-Hillman adducts of 2-(1H-pyrrol-1-yl)benzaldehydes with methyl acrylate or methyl vinyl ketone as a key step has been developed. (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis of 9-arylamino- and (Z)-9-arylimino-9H-pyrrolo[1,2-a]indoles by reactions of 2-(pyrrol-1-yl)benzaldehydes with aryl amines
  作者：Kazuhiro Kobayashi、Yasutoshi Himei、Shuhei Fukamachi、Miyuki Tanmatsu、Osamu Morikawa、Hisatoshi Konishi

  DOI：10.1016/j.tet.2007.02.129

  日期：2007.5

  Heating mixtures of 2-(pyrrol-1-yl)benzaldehydes and aryl amines under argon afforded 9-arylamino-9H-pyrrolo[1,2-a]indoles, via cyclization of the resulting 2-(pyrrol-1-yl)benzaldimine intermediates. Heating in the presence of oxygen afforded (Z)-9-arylimino-9H-pyrrolo[1,2-a]indoles, which were successfully hydrolyzed with hydrochloric acid to give pyrrolo[1,2-a]indol-9-ones.

  通过将所得的2-（吡咯-1-基）环合，在氩气下加热2-（吡咯-1-基）苯甲醛和芳基胺的混合物，得到9-芳基氨基-9 H-吡咯并[1,2- a ]吲哚。苯甲二胺中间体。在氧气存在下加热得到（Z）-9-芳基-9 H-吡咯并[1,2- a ]吲哚，将其成功地用盐酸水解，得到吡咯并[1,2 - a ]吲哚-9-ones。 。