1-(3,4-dichlorophenyl)-3-formylpyrrole | 848317-73-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-(3,4-dichlorophenyl)-3-formylpyrrole
• 英文别名: N-(3,4-dichlorophenyl)-3-formylpyrrole；1-(3,4-Dichlorophenyl)pyrrole-3-carbaldehyde
• CAS: 848317-73-7
• 化学式: C₁₁H₇Cl₂NO
• 分子量: 240.089
• InChiKey: YXIBAESOWDTIKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 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：

  (S)-1-[(2S,4R)-2-Hydroxy-4-((3S,4S)-3-hydroxy-chroman-4-ylcarbamoyl)-5-pyridin-3-yl-pentyl]-piperazine-2-carboxylic acid (2,2,2-trifluoro-ethyl)-amide 、 1-(3,4-dichlorophenyl)-3-formylpyrrole 在 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 (2S)-4-[[1-(3,4-dichlorophenyl)pyrrol-3-yl]methyl]-1-[(2S,4R)-2-hydroxy-5-[[(3S,4S)-3-hydroxychroman-4-yl]amino]-5-oxo-4-(3-pyridylmethyl)pentyl]-N-(2,2,2-trifluoroethyl)piperazine-2-carboxamide
  参考文献：
  名称：

  Novel HIV-1 protease inhibitors active against multiple PI-Resistant viral strains: coadministration with indinavir

  摘要：

  HIV-1 protease inhibitors (PI) with an N-arylpyrrole moiety in the P-3 position afforded excellent antiviral potency and substantially improved aqueous solubility over previously reported variants. The rapid in vitro clearance of these compounds in human liver microsomes prompted oral coadministration with indinavir to hinder their metabolism by the cyctochrome P450 3A4 isozyme and allow for in vivo PK assessment. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.08.049
• 作为产物：
  描述：

  1-(3,4-二氯苯基)-2-氧代吡咯烷-4-羧酸 在 sodium tetrahydroborate 、 碘 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 8.5h， 生成 1-(3,4-dichlorophenyl)-3-formylpyrrole
  参考文献：
  名称：

  Sodium borohydride–iodine mediated reduction of γ-lactam carboxylic acids followed by DDQ mediated oxidative aromatisation: a simple approach towards N-aryl-formylpyrroles and 1,3-diaryl-formylpyrroles

  摘要：

  A simple methodology for the conversion of substituted N-aryl-gamma-lactam 2/3-carboxylic acids to substituted N-aryl-2/3-formyl-pyrroles has been developed. Several N-aryl-gamma-lactam 2/3-carboxylic acids were reduced to substituted (N-aryl-pyrroliden-2/3-yl)-methanols in good yields by using the NaBH4-I-2 system. Aromatisation and in situ oxidation of these alcohols using DDQ produced N-aryl-2/3-formyl-pyrroles, which act as key starting material and intermediates in the synthesis of several bioactive compounds. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.01.058

文献信息

• Sodium borohydride–iodine mediated reduction of γ-lactam carboxylic acids followed by DDQ mediated oxidative aromatisation: a facile entry to N-aryl-formylpyrroles
  作者：Pranab Haldar、Joyram Guin、Jayanta K. Ray

  DOI：10.1016/j.tetlet.2004.12.107

  日期：2005.2

  A simple methodology for the conversion of substituted N-aryl-gamma-lactam 2/3-carboxylic acids to substituted N-aryl-2/3-formyl-pyrroles has been developed. Several N-aryl-gamma-lactam 2/3-carboxylic acids were reduced to substituted (N-arylpyri-olidine-2/3-yl)-methanols in good yields at room temperature using sodium borohydride-iodine. Controlled oxidation and aromatisation of these alcohols using DDQ produced N-aryl-2/3-formyl-pyrroles. (C) 2004 Elsevier Ltd. All rights reserved.