(3-aminopyridin-2-yl)acetonitrile | 1018949-67-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (3-aminopyridin-2-yl)acetonitrile
• 英文别名: 2-(3-aminopyridin-2-yl)acetonitrile
• CAS: 1018949-67-1
• 化学式: C₇H₇N₃
• mdl: MFCD16608699
• 分子量: 133.153
• InChiKey: ZRFOJSSSVSGJIC-UHFFFAOYSA-N

物化性质

• 沸点：
  346.4±27.0 °C(Predicted)
• 密度：
  1.198±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  62.7
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  存放于阴凉处，无活性气体环境中，室温保存。

反应信息

• 作为反应物：
  描述：

  2-吡啶甲酸 、 (3-aminopyridin-2-yl)acetonitrile 在 双(2-氧代-3-恶唑烷基)次磷酰氯 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 以80%的产率得到2-(pyridin-2-yl)-1H-pyrrolo[3,2-b]pyridine-3-carbonitrile
  参考文献：
  名称：

  通过修饰的Madelung吲哚合成方法可轻松获得3-氰基-4-氮杂吲哚

  摘要：

  描述了一种空前的方法，用于使用修饰的马德隆合成法轻松合成2-取代的3-氰基-4-氮杂吲哚。该方法依赖于非常温和条件下的酸和胺偶联。

  DOI：

  10.1016/j.tetlet.2013.10.025
• 作为产物：
  描述：

  2-(3-硝基吡啶-2-基)乙腈 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 26.0h， 以23.2 g的产率得到(3-aminopyridin-2-yl)acetonitrile
  参考文献：
  名称：

  A novel series of parenteral cephalosporins exhibiting potent activities against both Pseudomonas aeruginosa and other Gram-negative pathogens. Part 2: Synthesis and structure–activity relationships

  摘要：

  A novel series of 7 beta-[2-(2-amino-5-chloro-thiazol-4-yl)-2(Z)-((S)-1-carboxyethoxyimino)acetamido]cephalosporins bearing various pyridinium groups at the C-3' position were synthesized and their in vitro antibacterial activities against Gram-negative pathogens including Pseudomonas aeruginosa and several Gram-positive pathogens were evaluated. Among the cephalosporins prepared, we found that a cephalosporin bearing the 2- amino-1-(3-methylamino-propyl)-1H-imidazo[4,5-b] pyridinium group at the C-3' position (8a) showed potent and well-balanced antibacterial activities against P. aeruginosa and other Gram-negative pathogens including the strains which produce class C beta-lactamase and extended spectrum beta-lactamase (ESBL). Compound 8a also showed efficacious in vivo activity and high stability against AmpC beta-lactamase. These findings indicate that 2-aminoimidazopyridinium having an aminoalkyl group at the 1-position as a C-3' side chain is suitable for cephalosporins bearing an aminochlorothiazolyl moiety and a carboxyethoxyimino moiety on the C-7 side chain. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.11.028

文献信息

• Cyanomethylation of the Benzene Rings and Pyridine Rings via Direct Oxidative Cross-Dehydrogenative Coupling with Acetonitrile
  作者：Hua Yao、Xiaoyang Zhong、Bingqing Wang、Sen Lin、Zhaohua Yan

  DOI：10.1021/acs.orglett.2c00498

  日期：2022.3.18

  and efficient approach for the amine-directed dehydrogenative C(sp2)–C(sp3) coupling of arylamines with acetonitrile was reported by using FeCl2 as the catalyst. Substituted anilines, aminopyridines, naphthylamines, and some nitrogen-containing heterocyclic arylamines react with inactive acetonitrile to form the corresponding arylacetonitriles in moderate to good yields. This protocol features nontoxic

  报道了一种使用 FeCl 2作为催化剂的芳胺与乙腈的胺定向脱氢 C(sp 2 )-C(sp 3 ) 偶联的新型有效方法。取代的苯胺、氨基吡啶、萘胺和一些含氮杂环芳基胺与惰性乙腈反应生成相应的芳基乙腈，产率适中至高。该协议具有无毒的铁催化、高效的原子经济性、非预功能化的起始材料、良好的区域选择性以及官能团和芳环的良好相容性，为芳基乙腈提供了一种新颖、直接和绿色的方法。
• ISOQUINOLINONE DERIVATIVES AS NK3 ANTAGONISTS
  申请人：Khanzhin Nikolay

  公开号：US20110130407A1

  公开（公告）日：2011-06-02

  Isoquinolone derivatives of the general formula I are provided. The compounds are NK3 antagonists and useful for the treatment of e.g. psychosis and schizophrenia.

  提供一般式I的异喹啉衍生物。这些化合物是NK3拮抗剂，可用于治疗精神病和精神分裂症等疾病。
• Facile access to 3-cyano-4-azaindoles via a modified Madelung indole synthesis
  作者：Jagannath Jadhav、Sharanabasappa Khanapaure、Rajanikant Kurane、Rajashri Salunkhe、Gajanan Rashinkar

  DOI：10.1016/j.tetlet.2013.10.025

  日期：2013.12

  An unprecedented methodology for the facile synthesis of 2-substituted 3-cyano-4-azaindoles using modified Madelung synthesis is described. The methodology relies on acid and amine coupling under very mild conditions.

  描述了一种空前的方法，用于使用修饰的马德隆合成法轻松合成2-取代的3-氰基-4-氮杂吲哚。该方法依赖于非常温和条件下的酸和胺偶联。
• A novel series of parenteral cephalosporins exhibiting potent activities against both Pseudomonas aeruginosa and other Gram-negative pathogens. Part 2: Synthesis and structure–activity relationships
  作者：Kenji Yamawaki、Takashi Nomura、Tatsuro Yasukata、Norihiko Tanimoto、Koichi Uotani、Hideaki Miwa、Yoshinori Yamano、Kei Takeda、Yasuhiro Nishitani

  DOI：10.1016/j.bmc.2007.11.028

  日期：2008.2.15

  A novel series of 7 beta-[2-(2-amino-5-chloro-thiazol-4-yl)-2(Z)-((S)-1-carboxyethoxyimino)acetamido]cephalosporins bearing various pyridinium groups at the C-3' position were synthesized and their in vitro antibacterial activities against Gram-negative pathogens including Pseudomonas aeruginosa and several Gram-positive pathogens were evaluated. Among the cephalosporins prepared, we found that a cephalosporin bearing the 2- amino-1-(3-methylamino-propyl)-1H-imidazo[4,5-b] pyridinium group at the C-3' position (8a) showed potent and well-balanced antibacterial activities against P. aeruginosa and other Gram-negative pathogens including the strains which produce class C beta-lactamase and extended spectrum beta-lactamase (ESBL). Compound 8a also showed efficacious in vivo activity and high stability against AmpC beta-lactamase. These findings indicate that 2-aminoimidazopyridinium having an aminoalkyl group at the 1-position as a C-3' side chain is suitable for cephalosporins bearing an aminochlorothiazolyl moiety and a carboxyethoxyimino moiety on the C-7 side chain. (C) 2007 Elsevier Ltd. All rights reserved.