iso-butyl 1H-pyrrole-2-carboxylate | 864497-13-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: iso-butyl 1H-pyrrole-2-carboxylate
• 英文别名: (1H-pyrrol-2-yl) isobutyl formate；pyrrole-2-carboxylic acid isobutyl ester；Pyrrol-2-carbonsaeure-isobutylester；2-methylpropyl 1H-pyrrole-2-carboxylate
• CAS: 864497-13-2
• 化学式: C₉H₁₃NO₂
• mdl: MFCD20542539
• 分子量: 167.208
• InChiKey: UDCZOAOFHCQTNS-UHFFFAOYSA-N

物化性质

• 沸点：
  268.1±13.0 °C(Predicted)
• 密度：
  1.074±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.444
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  iso-butyl 1H-pyrrole-2-carboxylate 在 Selectfluor 作用下， 以 乙腈 为溶剂， 反应 0.08h， 以40%的产率得到isobutyl 5-fluoro-1H-pyrrole-2-carboxylate
  参考文献：
  名称：

  Microwave-Assisted Fluorination of 2-Acylpyrroles: Synthesis of Fluorohymenidin

  摘要：

  Treatment of mono- and nonbrominated 2-acylpyrroles with Selectfluor under microwave conditions leads to fluorination of the pyrrole ring in the 5-position. In particular, 2-trichloroacetylated pyrrole can be fluorinated. As an example, dihydrofluorohymenidin was synthesized and dehydrogenated to fluorohymenidin as the first fluorinated pyrrole-imidazole alkaloid. Introduction of the vinyl double bond was achieved by chlorination of the 2-aminoimidazole moiety, followed by dehydrochlorination at 100 degrees C in DMF.

  DOI：

  10.1021/ol2029993
• 作为产物：
  描述：

  2-(三氯乙酰)吡咯 、 异丁醇 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以91%的产率得到iso-butyl 1H-pyrrole-2-carboxylate
  参考文献：
  名称：

  Microwave-Assisted Fluorination of 2-Acylpyrroles: Synthesis of Fluorohymenidin

  摘要：

  Treatment of mono- and nonbrominated 2-acylpyrroles with Selectfluor under microwave conditions leads to fluorination of the pyrrole ring in the 5-position. In particular, 2-trichloroacetylated pyrrole can be fluorinated. As an example, dihydrofluorohymenidin was synthesized and dehydrogenated to fluorohymenidin as the first fluorinated pyrrole-imidazole alkaloid. Introduction of the vinyl double bond was achieved by chlorination of the 2-aminoimidazole moiety, followed by dehydrochlorination at 100 degrees C in DMF.

  DOI：

  10.1021/ol2029993

文献信息

• 一种吡咯酯类化合物的制备方法
  申请人：河南农业大学

  公开号：CN115093355A

  公开（公告）日：2022-09-23

  本发明涉及一种吡咯酯类化合物的制备方法，属于有机合成技术领域。本发明的吡咯酯类化合物的制备方法，包括下列步骤：将式A、式B或式C所示的化合物与醇类化合物在催化剂的作用下进行酯交换反应；所述醇类化合物具有式D或式E所示的结构；所述催化剂选自叔丁醇钠、叔丁醇钾、碳酸铯、六甲基二硅基氨基钾中的一种或任意组合。本发明的吡咯酯类化合物的制备方法，将吡咯甲酯或乙酯类化合物与醇类化合物进行酯交换反应，得到吡咯酯类化合物。本发明的吡咯酯类化合物的制备方法不需要惰性气体保护，可避免使用复杂催化剂，操作方便，简洁绿色高效，适合推广应用，并且制备的吡咯酯类化合物具有较高的收率。
• Anti-HIV-1 activity of pyrryl aryl sulfone (PAS) derivatives: synthesis and SAR studies of novel esters and amides at the position 2 of the pyrrole nucleus
  作者：Romano Silvestri、Marino Artico、Giuseppe La Regina、Gabriella De Martino、Massimiliano La Colla、Roberta Loddo、Paolo La Colla

  DOI：10.1016/j.farmac.2003.11.004

  日期：2004.3

  A SAR study has been performed in order to evaluate how much the ester function could be a determinant for the anti-human immunodeficiency virus type-1 activity of pyrryl aryl sulfones (PASs), a potent family of non-nucleoside reverse transcriptase (RT) inhibitors discovered in the last years. Twenty-three new esters were prepared with the aim to enhance the inhibitory potency of 4a and 4c, two PAS agents endowed with good activity (EC50 = 0.14 microM) and deprived of cytotoxicity up to >200 microM. None of test derivatives was as potent as 4a and 4c and lacked of selectivity due to their higher cytotoxicity (compounds 22-25). Antiviral activity correlate with an ester ramified chain.
• Oddo; Moschini, Gazzetta Chimica Italiana, 1912, vol. 42 II, p. 255
  作者：Oddo、Moschini

  DOI：——

  日期：——
• LOCAL ANESTHETICS IN THE PYRROLE SERIES. I^1,2
  作者：F. F. Blicke、E. S. Blake

  DOI：10.1021/ja01364a035

  日期：1930.1