cyclopentyl 1H-pyrrole-2-carboxylate | 685563-25-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: cyclopentyl 1H-pyrrole-2-carboxylate
• CAS: 685563-25-1
• 化学式: C₁₀H₁₃NO₂
• mdl: MFCD20542621
• 分子量: 179.219
• InChiKey: WRJAQRIQKBHDCR-UHFFFAOYSA-N

物化性质

• 熔点：
  61 °C(Solv: ligroine (8032-32-4))
• 沸点：
  119-120 °C(Press: 0.035-0.040 Torr)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  cyclopentyl 1H-pyrrole-2-carboxylate 在 18-冠醚-6 、 potassium tert-butylate 、 铁粉 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 5.75h， 生成 Cyclopentyl 1-(2-amino-5-chloro-phenyl)sulfonylpyrrole-2-carboxylate
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.farmac.2003.11.004
• 作为产物：
  描述：

  2-(三氯乙酰)吡咯 、 环戊醇 在 potassium carbonate 作用下， 反应 17.0h， 以96%的产率得到cyclopentyl 1H-pyrrole-2-carboxylate
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.farmac.2003.11.004

文献信息

• Palladium‐Catalysed Norbornene‐Mediated Regioselective Direct C−H Glycosylation of Free (<i>N−</i>H) Pyrrole Derivatives
  作者：Neha Singh Chauhan、Pintu Kumar Mandal

  DOI：10.1002/adsc.202301356

  日期：2024.3.19

  A palladium-catalyzed norbornene-mediated regioselective direct C−H glycosylation of free N-H pyrrole and electron-deficient pyrrole derivatives has been developed. The reaction involves the use of a PdII catalyst and norbornene as a transpositional co-catalyst, in which a pyrrole- and norbornyl-fused palladaheterocycle forms as the key intermediate. The 2-substituted pyrroles, and other 2,3-disubstituted

  已经开发出一种钯催化的降冰片烯介导的游离 NH 吡咯和缺电子吡咯衍生物的区域选择性直接 C−H 糖基化。该反应涉及使用 PdII 催化剂和降冰片烯作为转位助催化剂，其中吡咯和降冰片基稠合钯杂环形成作为关键中间体。 2-取代吡咯和其他2,3-二取代吡咯经历选择性C5糖基化。该反应与多种类型的糖基氯相容，包括 D-甘露糖、L-鼠李糖、D-呋喃甘露糖和 D-呋喃核糖。该策略的可行性通过克级、各种合成转化和功能化得以体现。