methyl 4-chloro-2-(1H-pyrrol-1-yl)benzoate | 847021-82-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: methyl 4-chloro-2-(1H-pyrrol-1-yl)benzoate
• 英文别名: methyl 4-chloro-2-pyrrol-1-ylbenzoate
• CAS: 847021-82-3
• 化学式: C₁₂H₁₀ClNO₂
• mdl: MFCD25121952
• 分子量: 235.67
• InChiKey: NJKFFWDNTOVYOD-UHFFFAOYSA-N

物化性质

• 熔点：
  50-52 °C
• 沸点：
  359.0±32.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.083
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 4-chloro-2-(1H-pyrrol-1-yl)benzoate 在 lithium aluminium tetrahydride 、 甲基磺酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 14.0h， 生成 1-(5-chloro-2-(chloromethyl)phenyl)-1H-pyrrole
  参考文献：
  名称：

  惰性N取代的吡咯的Brønsted酸催化环化生成苯并[f]吡咯并[1,2-a] [1,4]二氮杂s

  摘要：

  已经开发出两种分别涉及分子内和分子间环化的方法，以通过使用布朗斯台德酸催化剂直接和实际构建一系列重要的苯并[f]吡咯并[1,2-a] [1,4]氮杂。在TsOH催化下，3-羟基-2- [2-（2-（1H-吡咯-1-基）苄基]异吲哚啉-1-酮的分子内脱羟基/环闭合提供了各种外消旋苯并[f]吡咯并[1,2- a] [1,4]氮杂a类高产。此外，还通过手性磷酸催化将[2-（1H-吡咯-1-基）苯基]甲胺分子间加成而获得了对映体富集的苯并[f]吡咯并[1,2-a] [1,4]氮杂。甲酰苯甲酸酯在温和的条件下。

  DOI：

  10.1055/a-1468-5725
• 作为产物：
  描述：

  甲醇 、 4-chloro-2-pyrrol-1-yl-benzoic acid 在 硫酸 作用下， 生成 methyl 4-chloro-2-(1H-pyrrol-1-yl)benzoate
  参考文献：
  名称：

  ATP-Citrate Lyase as a Target for Hypolipidemic Intervention. 2. Synthesis and Evaluation of (3R*,5S*)-ω-Substituted-3-carboxy-3,5-dihydroxyalkanoic Acids and Their γ-Lactone Prodrugs as Inhibitors of the Enzyme in Vitro and in Vivo

  摘要：

  series of (3R*,5S*)-omega-substituted-3-carboxy-3,5-dihydroxyalkanoic acids have been synthesized and evaluated as inhibitors of the recombinant human form of ATP-citrate lyase. The best of these have K-i's in the 200-1000 nM range. As the corresponding thermodynamically favored gamma-lactone prodrugs, a number of compounds are able to inhibit cholesterol and fatty acid synthesis in HepG2 cells and reduce plasma triglyceride levels in vivo. The best of these, compound 77, is able to induce clear hypocholesterolemic and hypotriglyceridaemic responses when administered orally to rat and dog. These results provide evidence to support the hypothesis that compounds which inhibit ATP-citrate lyase have the potential to be a novel class of hypolipidemic agent, which possess combined hypocholesterolemic and hypotriglyceridemic activities.

  DOI：

  10.1021/jm980091z

文献信息

• Synthesis of Condensed Pyrroloindoles via Pd-Catalyzed Intramolecular C−H Bond Functionalization of Pyrroles
  作者：Seung Jun Hwang、Seung Hwan Cho、Sukbok Chang

  DOI：10.1021/ja806897h

  日期：2008.12.3

  the synthesis of condensed hetero- or carbocycles such as pyrroloindoles or fluorenes has been developed that involves the Pd-catalyzed cyclization of readily available N-(2-halobenzyl)pyrroles or their phenyl derivatives. The reaction is proposed to proceed via oxidative addition of benzylic halides to Pd(0) followed by base-assisted C-H bond activation. A broad range of condensed cyclic products could

  已开发出一种合成稠合杂环或碳环（如吡咯并吲哚或芴）的新策略，该策略涉及 Pd 催化的易于获得的 N-（2-卤代苄基）吡咯或其苯基衍生物的环化。建议该反应通过将苄基卤化物氧化加成到 Pd(0) 上，然后碱辅助 CH 键活化来进行。可以在温和条件下以良好到极好的收率获得范围广泛的稠环产物。
• 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.
• Brønsted Acid Catalyzed Cyclization of Inert N-Substituted Pyrroles to Benzo[f]pyrrolo[1,2-a][1,4]diazepines
  作者：Jinlong Zhang、Gaoxi Jiang、Zeng Gao、Jinlong Qian、Huameng Yang

  DOI：10.1055/a-1468-5725

  日期：2021.6

  construction of a series of important benzo[f]pyrrolo[1,2-a][1,4]azepines by using Brønsted acid catalysts. Upon catalysis by TsOH, the intramolecular dehydroxylation/ring closure of 3-hydroxy-2-[2-(1H-pyrrol-1-yl)benzyl]isoindolin-1-ones provided various racemic benzo[f]pyrrolo[1,2-a][1,4]azepines in high yields. Furthermore, enantioenriched benzo[f]pyrrolo[1,2-a][1,4]azepines were also obtained by chiral

  已经开发出两种分别涉及分子内和分子间环化的方法，以通过使用布朗斯台德酸催化剂直接和实际构建一系列重要的苯并[f]吡咯并[1,2-a] [1,4]氮杂。在TsOH催化下，3-羟基-2- [2-（2-（1H-吡咯-1-基）苄基]异吲哚啉-1-酮的分子内脱羟基/环闭合提供了各种外消旋苯并[f]吡咯并[1,2- a] [1,4]氮杂a类高产。此外，还通过手性磷酸催化将[2-（1H-吡咯-1-基）苯基]甲胺分子间加成而获得了对映体富集的苯并[f]吡咯并[1,2-a] [1,4]氮杂。甲酰苯甲酸酯在温和的条件下。
• ATP-Citrate Lyase as a Target for Hypolipidemic Intervention. 2. Synthesis and Evaluation of (3<i>R</i>*,5<i>S</i>*)-ω-Substituted-3-carboxy-3,5-dihydroxyalkanoic Acids and Their γ-Lactone Prodrugs as Inhibitors of the Enzyme in Vitro and in Vivo
  作者：Andrew D. Gribble、Robert J. Ife、Antony Shaw、David McNair、Christine E. Novelli、Susan Bakewell、Virendra P. Shah、Roland E. Dolle、Pieter H. Groot、Nigel Pearce、John Yates、David Tew、Helen Boyd、Stephen Ashman、Drake S. Eggleston、R. Curtis Haltiwanger、George Okafo

  DOI：10.1021/jm980091z

  日期：1998.9.1

  series of (3R*,5S*)-omega-substituted-3-carboxy-3,5-dihydroxyalkanoic acids have been synthesized and evaluated as inhibitors of the recombinant human form of ATP-citrate lyase. The best of these have K-i's in the 200-1000 nM range. As the corresponding thermodynamically favored gamma-lactone prodrugs, a number of compounds are able to inhibit cholesterol and fatty acid synthesis in HepG2 cells and reduce plasma triglyceride levels in vivo. The best of these, compound 77, is able to induce clear hypocholesterolemic and hypotriglyceridaemic responses when administered orally to rat and dog. These results provide evidence to support the hypothesis that compounds which inhibit ATP-citrate lyase have the potential to be a novel class of hypolipidemic agent, which possess combined hypocholesterolemic and hypotriglyceridemic activities.