(1H-吡咯-2-基)乙腈 | 50551-29-6

• 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-基)乙腈
• 中文别名: 吡咯-2-乙腈
• 英文名称: 2-pyrroleacetonitrile
• 英文别名: 2-(1H-pyrrol-2-yl)acetonitrile；1H-pyrrol-2-acetonitrile
• CAS: 50551-29-6
• 化学式: C₆H₆N₂
• mdl: MFCD09878875
• 分子量: 106.127
• InChiKey: MKVATVUOVMCHJJ-UHFFFAOYSA-N

物化性质

• 沸点：
  110-115 °C(Press: 2 Torr)
• 密度：
  1.129±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  39.6
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  (1H-吡咯-2-基)乙腈 在 lithium aluminium tetrahydride 、 乙醚 作用下， 生成 2-(2-吡咯基)乙胺
  参考文献：
  名称：

  β-2-Pyrrole-ethylamine

  摘要：

  DOI：

  10.1021/ja01098a504
• 作为产物：
  描述：

  2-(benzenesulfinylmethyl)-1H-pyrrole 生成 (1H-吡咯-2-基)乙腈
  参考文献：
  名称：

  1-and 2-azafulvenes

  摘要：

  Flash pyrolysis of dialkylaminopyrroles and thermolysis of 2-pyrrylmethyl phenyl sulfoxide at 65-degrees-C in solution gave azafulvenes which were trapped with a variety of nucleophiles.

  DOI：

  10.1016/s0040-4039(00)77524-1

文献信息

• [EN] AZOLE METHYLIDENE CYANIDE DERIVATIVES AND THEIR USE AS PROTEIN KINASE MODULATORS<br/>[FR] DERIVES DE CYANURE D'AZOLE METHYLIDENE ET LEUR UTILISATION COMME MODULATEURS DE PROTEINE KINASE
  申请人：APPLIED RESEARCH SYSTEMS

  公开号：WO2003106455A1

  公开（公告）日：2003-12-24

  The present invention is related to azole derivatives notably for use as pharmaceutically active compounds, as well as to pharmaceutical formulations containing such azole derivatives. Said azole derivatives are modulators of the protein kinase signalling pathways, particularly the one involving c-Jun N-terminal kinase and/or Glycogen Kinase Synthase 3. The present invention is furthermore related to novel azole derivatives as well as to methods of their preparation. X is O, S or NR0, with R0 being H or an unsubstituted or substituted C1 -C6 alkyl; A is 2-pyridyl, 3-pyridyl, 4-pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl or triazinyl group.

  本发明涉及唑衍生物，尤其是用作药物活性化合物的唑衍生物，以及包含这种唑衍生物的药物制剂。所述唑衍生物是蛋白激酶信号通路的调节剂，尤其是涉及c-Jun N端激酶和/或糖原合酶3的那一种。本发明还涉及新颖的唑衍生物以及它们的制备方法。X是O、S或NR0，其中R0是H或未取代或取代的C1-C6烷基；A是2-吡啶基，3-吡啶基，4-吡啶基，吡啶唑基，吡唑啉基，吡嗪基或三嗪基团。
• Rapid nitrosamine formation from a tertiary amine: The nitrosation of 2-(N,N-Dimethylaminomethyl)pyrrole
  作者：R.N. Loeppky、J.R. Outram、W. Tomasik、J.M. Faulconer

  DOI：10.1016/s0040-4039(00)88318-5

  日期：1983.1

  2-(N,N-Dimethylaminomethyl)pyrrole reacts instantaneously with nitrous acid at 25° to produce diemthylnitrosamine, maleimidemonooxine, formaldehyde and other products. The data implicate new mechanisms of tertiary amine nitrosation.

  2-（N，N-二甲基氨基甲基）吡咯与亚硝酸在25°C下瞬间反应生成二甲基亚硝胺，顺丁烯二酰亚胺，甲醛和其他产物。数据暗示了叔胺亚硝化的新机理。
• Nickel/Lewis Acid-Catalyzed Carbocyanation of Alkynes Using Acetonitrile and Substituted Acetonitriles
  作者：Akira Yada、Tomoya Yukawa、Hiroaki Idei、Yoshiaki Nakao、Tamejiro Hiyama

  DOI：10.1246/bcsj.20100023

  日期：2010.6.15

  Nickel/Lewis acid dual catalysis is found to effect the carbocyanation reaction of alkynes using acetonitrile and substituted acetonitriles to give a range of variously substituted acrylonitriles. The addition of propionitrile across alkynes is also demonstrated briefly to give the corresponding ethylcyanation products in good yields, whereas the reaction of butyronitrile gives significant amounts of hydrocyanation products due possibly to β-hydride elimination of a propylnickel intermediate. The reaction of optically active α-phenylpropionitrile suggests a reaction mechanism that involves oxidative addition of a C–CN bond with retention of its absolute configuration.

  镍/路易斯酸双催化体系被发现能够有效地促进乙腈和取代乙腈与炔烃的碳氰化反应，生成一系列不同取代的丙烯腈。简要展示的丙腈与炔烃的加成反应也能高效地得到相应的乙基氰化产物，而丁腈参与的反应则因可能的丙基镍中间体β-氢消除作用而得到显著量的氢氰化产物。光学活性α-苯基丙腈的反应表明其反应机制涉及C–CN键的氧化加成，并保留其绝对构型。
• Photochemical generation of radicals from alkyl electrophiles using a nucleophilic organic catalyst
  作者：Bertrand Schweitzer-Chaput、Matthew A. Horwitz、Eduardo de Pedro Beato、Paolo Melchiorre

  DOI：10.1038/s41557-018-0173-x

  日期：2019.2

  extensively use free radical reactivity for applications in organic synthesis, materials science, and life science. Traditionally, generating radicals requires strategies that exploit the bond dissociation energy or the redox properties of the precursors. Here, we disclose a photochemical catalytic approach that harnesses different physical properties of the substrate to form carbon radicals. We use a nucleophilic

  化学家在有机合成，材料科学和生命科学中广泛使用自由基反应性。传统上，产生自由基需要利用键解离能或前体的氧化还原特性的策略。在这里，我们公开了一种光化学催化方法，该方法利用了基材的不同物理特性来形成碳自由基。我们使用亲核性的二硫代氨基甲酸酯阴离子催化剂，配以量身定制的发色单元，以通过S N 2途径活化烷基亲电体。所得的吸收光子的中间体在由可见光诱导的均相裂解时提供自由基。此催化性S N基于2的策略利用了离子化学的基本机理过程，可以从各种底物中获得与经典自由基生成策略不兼容或惰性的开壳中间体的访问权限。我们还描述了该方法温和的反应条件和较高的官能团耐受性如何有利于开发C–C键形成反应，简化市售药物的制备，生物相关化合物的后期精制以及对映选择性自由基催化。
• Radical aromatic substitution via atom-transfer addition
  作者：Jeffrey H. Byers、John E. Campbell、Faith H. Knapp、Jameson G. Thissell

  DOI：10.1016/s0040-4039(99)00304-4

  日期：1999.4

  New methodology for radical aromatic substitution has been developed involving the addition of electron-deficient radicals to unprotected pyrroles and indole. This non-oxidative process is presumed to be occurring via atom-transfer addition of suitable organoiodides and bromides with subsequent non-radical elimination of HI or HBr, respectively. The process also occurs under stannane-free conditions

  已经开发出用于自由基芳族取代的新方法，该方法涉及将电子不足的自由基添加到未保护的吡咯和吲哚中。推测该非氧化过程是通过合适的有机碘和溴化物的原子转移添加以及随后分别无自由基地消除HI或HBr发生的。该过程也发生在不含锡的条件下。