ethyl 2-(5-formyl-1H-pyrrol-2-yl)ethanoate | 345971-24-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-(5-formyl-1H-pyrrol-2-yl)ethanoate
• 英文别名: ethyl 2-(5-formyl-1H-pyrrol-2-yl)acetate
• CAS: 345971-24-6
• 化学式: C₉H₁₁NO₃
• 分子量: 181.191
• InChiKey: BFEFRSAHYSEOGT-UHFFFAOYSA-N

物化性质

• 沸点：
  310.7±32.0 °C(Predicted)
• 密度：
  1.218±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  59.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 2-(5-formyl-1H-pyrrol-2-yl)ethanoate 在 sodium hydroxide 、 zinc(II) tetrahydroborate 、 sodium hydride 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 17.5h， 生成 (S)-2-[2-(5-Hydroxymethyl-1-methanesulfonyl-1H-pyrrol-2-yl)-acetylamino]-4-methyl-pentanoic acid methyl ester
  参考文献：
  名称：

  Ring-deactivated hydroxymethylpyrroles as inhibitors of α-chymotrypsin

  摘要：

  N-Acyl and N-sulfonylhydroxymetyhylpyrroles have been synthesised and shown to inhibit alpha -chymotrypsin. A hydrophobic group in the N-substituent has been shown to be required for activity. O 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00274-1
• 作为产物：
  描述：

  2-吡咯甲醛 、 2-((乙氧基碳硫代)硫代)乙酸乙酯 在 三乙基硼 、 iron(II) sulfate 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 14.0h， 以65%的产率得到ethyl 2-(5-formyl-1H-pyrrol-2-yl)ethanoate
  参考文献：
  名称：

  Et3B-Mediated radical alkylation of pyrroles and indoles

  摘要：

  An efficient Et3B-mediated oxidative radical substitution of substituted pyrroles and indoles using xanthate based radical chemistry in the presence of iron(II) sulfate is described. Unsubstituted indole gave only low yield or failed in the process. 2-Cyano-furan and 2-benzoylthiophene did not afford the corresponding alkylated products under these conditions. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.02.052

文献信息

• [EN] NOVEL COMPOUNDS AND METHODS OF USING THEM<br/>[FR] NOUVEAUX COMPOSÉS ET LEURS PROCÉDÉS D'UTILISATION
  申请人：SYNDAX PHARMACEUTICALS INC

  公开号：WO2009015180A2

  公开（公告）日：2009-01-29

  The present invention relates to novel compounds and their pharmaceutically acceptable salts, prodrugs, solvates, polymorphs, tautomers and isomers. In some embodiments, the compounds described herein may be used to modulate sirtuins (SIRT). The present invention also relates to methods for modulating sirtuins. The present invention also relates to methods useful in the treatment of diseases.
• Ring-deactivated hydroxymethylpyrroles as inhibitors of α-chymotrypsin
  作者：Andrew D. Abell、Brent K. Nabbs

  DOI：10.1016/s0968-0896(00)00274-1

  日期：2001.3

  N-Acyl and N-sulfonylhydroxymetyhylpyrroles have been synthesised and shown to inhibit alpha -chymotrypsin. A hydrophobic group in the N-substituent has been shown to be required for activity. O 2001 Elsevier Science Ltd. All rights reserved.
• Et3B-Mediated radical alkylation of pyrroles and indoles
  作者：Miguel A. Guerrero、Luis D. Miranda

  DOI：10.1016/j.tetlet.2006.02.052

  日期：2006.4

  An efficient Et3B-mediated oxidative radical substitution of substituted pyrroles and indoles using xanthate based radical chemistry in the presence of iron(II) sulfate is described. Unsubstituted indole gave only low yield or failed in the process. 2-Cyano-furan and 2-benzoylthiophene did not afford the corresponding alkylated products under these conditions. (c) 2006 Elsevier Ltd. All rights reserved.