1H-吡咯-2-胺,1-甲基- | 173853-66-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 1H-吡咯-2-胺,1-甲基-
• 英文名称: 2-amino-1-methylpyrrol
• 英文别名: 1-Methyl-1H-pyrrol-2-amine；1-methylpyrrol-2-amine
• CAS: 173853-66-2
• 化学式: C₅H₈N₂
• 分子量: 96.1319
• InChiKey: JWUNKWDORORNKY-UHFFFAOYSA-N

物化性质

• 熔点：
  158-159 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  203.9±13.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  31
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-(1-methyl-3-trifluoromethyl-1H-pyrazol-5-yl)-2-thiophenecarbonylchloride 、 1H-吡咯-2-胺,1-甲基- 在 碳酸氢钠 作用下， 以 二氯甲烷 、 水 为溶剂， 以36%的产率得到N-(1-methyl-2-pyrrolyl)-5-(1-methyl-3-trifluoromethyl-1H-pyrazol-5-yl)thiophene-2-carboxamide
  参考文献：
  名称：

  Novel potent and selective calcium-release-activated calcium (CRAC) channel inhibitors. Part 1: Synthesis and inhibitory activity of 5-(1-methyl-3-trifluoromethyl-1H-pyrazol-5-yl)-2-thiophenecarboxamides

  摘要：

  We synthesized and evaluated a series of 5-(1-methyl-3-trifluoromethyl-1H-pyrazol-5-yl)-2-thiophenecarboxamides to identify potent inhibitors of calcium-release-activated calcium (CRAC) channels with greater selectivity than voltage-operated calcium (VOC) channels. These efforts resulted in identification of compounds 22 and 24. The former exhibits highly potent and selective CRAC channel inhibitory activity, and the latter inhibited phytohemagglutinin-induced interleukin-2 production by Jurkat T lymphocytes and concanavalin A-induced hepatitis in mice. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.03.024
• 作为产物：
  描述：

  N-(1-methyl-1H-pyrrol-2-yl)-o-hydroxymethylbenzamide 在 溶剂黄146 作用下， 反应 2.0h， 生成 1H-吡咯-2-胺,1-甲基-
  参考文献：
  名称：

  Preparation and Characterization of Tetraphenylborate Salts of 2-Aminopyrrole and 1-Alkyl-2-aminopyrroles

  摘要：

  制备了 2-氨基吡咯和 1-烷基-2-氨基吡咯的四苯基硼酸盐，并发现其是稳定的。

  DOI：

  10.1039/a809138b

文献信息

• 一种催化氧化羰基化合成不对称二取代脲的 方法
  申请人：南京师范大学

  公开号：CN107417478B

  公开（公告）日：2020-05-05

  本发明公开了一种直接合成不对称二取代脲类化合物的新方法，在溶剂聚乙二醇或聚乙二醇的水溶液中，在碱、碘化物和氧化剂的作用下，加入钯催化剂，催化伯胺与一氧化碳的直接交叉偶联反应制备不对称二取代脲类化合物。本发明的偶联反应制备不对称二取代脲类化合物的方法，具有具有氧化剂来源广泛和环境友好；底物来源广泛、廉价和易于处理；羰基源稳定、廉价和不产生废物；反应无需配体且活性好；反应条件温和且选择性高；底物官能团相容性好且底物的适用范围广；反应介质绿色且可以循环回收的优势。在优化的反应条件之下，目标产品分离收率可高达97％左右。
• First synthesis of 2-aminopyrrole and simple 1-substituted-2-aminopyrroles. Observation of fast proton exchange at C-5.
  作者：Michael De Rosa、Roy P. Issac、Gregory Houghton

  DOI：10.1016/0040-4039(95)02019-l

  日期：1995.12

  N-(1-substituent-111-pyrrol-2-yl)phlhalimides can be used to prepare the previously unknown 2-aminopyrrole and 1-substituted 2-aminopyrroles which undergo fast proton exchange at C-5 in acetic acid at 25 °C.

  N-（1-取代基-1 11-吡咯-2-基）邻苯二甲酰亚胺可用于制备先前未知的2-氨基吡咯和1-取代的2-氨基吡咯，它们在25°C的乙酸中于C-5进行快速质子交换C。
• Design and Synthesis of N-phenyl Phthalimides as Potent Protoporphyrinogen Oxidase Inhibitors
  作者：Wei Gao、Xiaotian Li、Da Ren、Susu Sun、Jingqian Huo、Yanen Wang、Lai Chen、Jinlin Zhang

  DOI：10.3390/molecules24234363

  日期：——

  Protoporphyrinogen oxidase (PPO) has been identified as one of the most promising targets for herbicide discovery. A series of novel phthalimide derivatives were designed by molecular docking studies targeting the crystal structure of mitochondrial PPO from tobacco (mtPPO, PDB: 1SEZ) by using Flumioxazin as a lead, after which the derivatives were synthesized and characterized, and their herbicidal

  原卟啉原氧化酶 (PPO) 已被确定为最有希望的除草剂发现目标之一。以氟虫嗪为先导物，针对烟草线粒体PPO（mtPPO，PDB：1SEZ）的晶体结构，通过分子对接研究设计了一系列新型邻苯二甲酰亚胺衍生物，随后合成并表征了这些衍生物，并随后对其除草活性进行了研究。评估。除草剂生物测定结果表明，3a(2-(4-bromo-2,6-difluorophenyl)isoindoline-1,3-dione)、3d(methyl 2-(4-chloro-1,3-dioxoisoindolin-2 -yl)-5-氟苯甲酸酯), 3g (4-chloro-2-(5-methylisoxazol-3-yl)isoindoline-1,3-dione), 3j (4-chloro-2-(thiophen-2-ylmethyl) isoindoline-1,3-dione)和3r(2-(4-bromo-2,6
• EFFECT OF ELECTRON-WITHDRAWING SUBSTITUENTS ON THE INVERSE-ELECTRON DEMAND DIELS-ALDER REACTION OF 2-AMINOPYRROLES AND 1,3,5-TRIAZINES
  作者：Michael De Rosa、David Arnold、Eric Blythe、Martilias S. Farrell、Tamika Seals、Kristin Wills、Miroslav Medved

  DOI：10.1515/hc.2007.13.2-3.97

  日期：2007.1
• Novel potent and selective calcium-release-activated calcium (CRAC) channel inhibitors. Part 1: Synthesis and inhibitory activity of 5-(1-methyl-3-trifluoromethyl-1H-pyrazol-5-yl)-2-thiophenecarboxamides
  作者：Yasuhiro Yonetoku、Hirokazu Kubota、Yoshinori Okamoto、Akira Toyoshima、Masashi Funatsu、Jun Ishikawa、Makoto Takeuchi、Mitsuaki Ohta、Shin-ichi Tsukamoto

  DOI：10.1016/j.bmc.2006.03.024

  日期：2006.7.15

  We synthesized and evaluated a series of 5-(1-methyl-3-trifluoromethyl-1H-pyrazol-5-yl)-2-thiophenecarboxamides to identify potent inhibitors of calcium-release-activated calcium (CRAC) channels with greater selectivity than voltage-operated calcium (VOC) channels. These efforts resulted in identification of compounds 22 and 24. The former exhibits highly potent and selective CRAC channel inhibitory activity, and the latter inhibited phytohemagglutinin-induced interleukin-2 production by Jurkat T lymphocytes and concanavalin A-induced hepatitis in mice. (c) 2006 Elsevier Ltd. All rights reserved.