2-(3-nitrophenyl)-1H-pyrrole | 912763-15-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-(3-nitrophenyl)-1H-pyrrole
• 英文别名: 2-(3-nitro-phenyl)-pyrrole；m-Nitrophenylpyrrole
• CAS: 912763-15-6
• 化学式: C₁₀H₈N₂O₂
• 分子量: 188.186
• InChiKey: DJWVNJKOGMRQDU-UHFFFAOYSA-N

物化性质

• 沸点：
  389.7±25.0 °C(Predicted)
• 密度：
  1.298±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(3-nitrophenyl)-1H-pyrrole 在 4-二甲氨基吡啶 、 lithium hydroxide 、 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 、 tin(ll) chloride 作用下， 以 四氢呋喃 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 51.25h， 生成 (2-(3-(2-(5-cyclohexyl-1-(3,3-dimethyl-2-oxo-butyl)-2-oxo-1,2-dihydro-3H-1,3,4-benzotriazepin-3-yl)-acetylamino)-phenyl)-pyrrol-1-yl)-acetic acid
  参考文献：
  名称：

  Optimization of 1,3,4-Benzotriazepine-Based CCK₂ Antagonists to Obtain Potent, Orally Active Inhibitors of Gastrin-Mediated Gastric Acid Secretion

  摘要：

  Starting from a novel, achiral 1,3,4-benzotriazepine-based CCK2 receptor antagonist, a process of optimization has afforded further compounds of this type that maintain the nanomolar affinity for recombinant, human CCK2 receptors and high selectivity over CCK1 receptors observed in the initial lead but display more potent inhibition of pentagastrin-stimulated gastric acid secretion in vivo. Moreover, this has largely been achieved without altering their potency at wild-type canine and rat receptors, as judged by their displacement of [I-125]-BH-CCK-8S in a radioligand binding assay and by their activity in an isolated, perfused rat stomach bioassay, respectively. 2-(5-Cyclohexyl-1-(2-cyclopentyl-2-oxo-ethyl)-2-oxo-1,2-dihydro-3H-1,3,4-benzotriazepin-3-yl)-N-(3-(5-oxo-2,5-dihydro- [1,2,4]oxadiazol-3-yl)-phenyl)-acetamide (47) was identified as the most effective compound stemming from this approach, proving to be a potent inhibitor of pentagastrin-stimulated gastric acid secretion in rats and dogs by intravenous bolus as well as by enteral administration.

  DOI：

  10.1021/jm070139l
• 作为产物：
  描述：

  1-(4-甲基苯基)磺酰基-2-(3-硝基苯基)吡咯 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 2-(3-nitrophenyl)-1H-pyrrole
  参考文献：
  名称：

  2-Bromo-N-(p-toluenesulfonyl)pyrrole: A Robust Derivative of 2-Bromopyrrole

  摘要：

  2-溴-N-(对甲苯磺酰基)吡咯 (2) 是2-溴吡咯 (1) 的一种晶体稳定衍生物，通过对吡咯进行溴化，然后转化为N-(对甲苯磺酰基)衍生物，得到了80%的产率。该化合物在常温下可以无限期稳定。化合物2是与芳基硼酸进行铃木偶联反应的优秀底物。

  DOI：

  10.1055/s-2003-42036

文献信息

• Concise Access to 1,2-Pyrrole-Annulated Benzazepines through a Brønsted Acid Catalyzed Redox-Neutral Domino Reaction
  作者：Peng-Fei Wang、Ya-Ping Huang、Xiaoan Wen、Hongbin Sun、Qing-Long Xu

  DOI：10.1002/ejoc.201501006

  日期：2015.10

  A Bronsted acid catalyzed redox-annulated cascade reaction between 2-arylpyrroles and 2-(pyrrolidin-1-yl)-, 2-(piperidin-1-yl), or 2-morpholinobenzaldehydes has been developed. This dehydration/1,5-hydride shift/cyclization sequence results in the construction of two new C(sp2)–C(sp3) bonds, providing structurally diverse 1,2-pyrrole-annulated benzazepines in yields of 25–65 %.

  已开发出布朗斯台德酸催化的 2-芳基吡咯和 2-(吡咯烷-1-基)-、2-(哌啶-1-基) 或 2-吗啉代苯甲醛之间的氧化还原环化级联反应。这种脱水/1,5-氢化物转移/环化序列导致构建两个新的 C(sp2)–C(sp3) 键，以 25–65% 的产率提供结构多样化的 1,2-吡咯环化苯并氮杂。
• Iron-Mediated Direct Suzuki−Miyaura Reaction: A New Method for the <i>ortho</i>-Arylation of Pyrrole and Pyridine
  作者：Jun Wen、Song Qin、Li-Fang Ma、Liang Dong、Ji Zhang、Shan-Shan Liu、Yi-Shu Duan、Shan-Yong Chen、Chang-Wei Hu、Xiao-Qi Yu

  DOI：10.1021/ol100838m

  日期：2010.6.18

  The first example of an iron-mediated direct Suzuki-Miyaura reaction between N-heterocyclic compounds and arylboronic acids is described, and both electron-rich and electron-deficient heteroarenes can be successfully used for the coupling reaction.
• Direct Arylation of Arene and <i>N</i>-Heteroarenes with Diaryliodonium Salts without the Use of Transition Metal Catalyst
  作者：Jun Wen、Ruo-Yi Zhang、Shan-Yong Chen、Ji Zhang、Xiao-Qi Yu

  DOI：10.1021/jo202150t

  日期：2012.1.6

  A novel and simple transition metal-free direct arylation of arene and N-heteroarenes with diaryliodonium salts has been developed. This cross-coupling reaction is promoted only by base and gives the desired products in moderate to good yields.
• Optimization of 1,3,4-Benzotriazepine-Based CCK₂ Antagonists to Obtain Potent, Orally Active Inhibitors of Gastrin-Mediated Gastric Acid Secretion
  作者：Iain M. McDonald、James W. Black、Ildiko M. Buck、David J. Dunstone、Eric P. Griffin、Elaine A. Harper、Robert A. D. Hull、S. Barret Kalindjian、Elliot J. Lilley、Ian D. Linney、Michael J. Pether、Sonia P. Roberts、Mark E. Shaxted、John Spencer、Katherine I. M. Steel、David A. Sykes、Martin K. Walker、Gillian F. Watt、Laurence Wright、Paul T. Wright、Wei Xun

  DOI：10.1021/jm070139l

  日期：2007.6.1

  Starting from a novel, achiral 1,3,4-benzotriazepine-based CCK2 receptor antagonist, a process of optimization has afforded further compounds of this type that maintain the nanomolar affinity for recombinant, human CCK2 receptors and high selectivity over CCK1 receptors observed in the initial lead but display more potent inhibition of pentagastrin-stimulated gastric acid secretion in vivo. Moreover, this has largely been achieved without altering their potency at wild-type canine and rat receptors, as judged by their displacement of [I-125]-BH-CCK-8S in a radioligand binding assay and by their activity in an isolated, perfused rat stomach bioassay, respectively. 2-(5-Cyclohexyl-1-(2-cyclopentyl-2-oxo-ethyl)-2-oxo-1,2-dihydro-3H-1,3,4-benzotriazepin-3-yl)-N-(3-(5-oxo-2,5-dihydro- [1,2,4]oxadiazol-3-yl)-phenyl)-acetamide (47) was identified as the most effective compound stemming from this approach, proving to be a potent inhibitor of pentagastrin-stimulated gastric acid secretion in rats and dogs by intravenous bolus as well as by enteral administration.
• 2-Bromo<i>-N-</i>(<i>p-</i>toluenesulfonyl)pyrrole: A Robust Derivative of 2-Bromopyrrole
  作者：John W. Huffman、Lea W. Knight、Matthew L. Isherwood

  DOI：10.1055/s-2003-42036

  日期：——

  2-Bromo-N-(p-toluenesulfonyl)pyrrole (2), a crystalline stable derivative of 2-bromopyrrole (1) has been prepared in 80% yield by bromination of pyrrole, followed by conversion to the N-(p-toluenesulfonyl) derivative. This compound is stable indefinitely at ambient temperature. Compound 2 is an excellent substrate for Suzuki coupling with arylboronic acids.

  2-溴-N-(对甲苯磺酰基)吡咯 (2) 是2-溴吡咯 (1) 的一种晶体稳定衍生物，通过对吡咯进行溴化，然后转化为N-(对甲苯磺酰基)衍生物，得到了80%的产率。该化合物在常温下可以无限期稳定。化合物2是与芳基硼酸进行铃木偶联反应的优秀底物。