5-chloro-2-pyridyl isonitrile | 1027746-23-1

• 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: 5-chloro-2-pyridyl isonitrile
• 英文别名: 5-chloro-2-isocyanopyridine
• CAS: 1027746-23-1
• 化学式: C₆H₃ClN₂
• mdl: MFCD03789585
• 分子量: 138.556
• InChiKey: IOOLWTVXWRNWHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-chloro-2-pyridyl isonitrile 以 1,4-二氧六环 为溶剂， 以53%的产率得到2,8-dichloropyrido[2'',1'':2',3']imidazo[4',5':4,5]imidazo[1,2-a]pyridine
  参考文献：
  名称：

  Dimerization of 2-pyridylisonitriles produces π-extended fused heteroarenes useful as highly selective colorimetric and optical probes for copper ion

  摘要：

  A very simple synthesis of pyrido[2 '',1 '':2',3']imidazo[4',5':4,5]imidazo[1,2-a]Pyridines 2 was achieved from the dimerization of 2-pyridylisonitriles. The optical responses of these pi-extended fused heteroarenes to a series of metal ions were investigated by means of UV-visible absorption spectrum in acetonitrile. It was found that most of compounds 2 selectively responded to Cu2+, and the limit of detection was about 3.5 x 10(-7) M when using the best probe, 3,9-dimethylpyrido[2",1":2',3']imidazo[4',5':4,5] imidazol1,2-a]pyridine 2d. Meanwhile some compounds 2 specifically showed a color change from colorless to red or yellow when they are exposed to copper ion in acetonitrile, whereas other transitional, alkali and alkaline earth metal ions could not induce a color change. This work not only established a direct access to pi-extended fused heteroarenes, but also supplied novel sensitive and selective colorimetric and optical probes for copper ion. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.06.096
• 作为产物：
  描述：

  N-(5-chloropyridin-2-yl)formamide 在 三乙胺 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 以36%的产率得到5-chloro-2-pyridyl isonitrile
  参考文献：
  名称：

  2-溴-6-异氰基吡啶是用于多组分化学的通用可转换异氰酸酯

  摘要：

  据报道2-异氰基吡啶是用于多组分化学的新型可转化异氰酸酯。对该类别的12位代表进行的比较显示，就稳定性和合成效率而言，2-溴-6-异氰基吡啶是最佳试剂。它在碱性和酸性条件下都具有足够的亲核性和所得酰胺部分的良好离去基团能力。为了证明该试剂的实用性，提出了有效的两步有效合成有效的阿片样物质芬太尼。

  DOI：

  10.1021/acs.orglett.6b00091

文献信息

• Silver-Catalyzed Chemoselective [4+2] Annulation of Two Isocyanides: A General Route to Pyridone-Fused Carbo- and Heterocycles
  作者：Zhongyan Hu、Jinhuan Dong、Yang Men、Zhichen Lin、Jinxiong Cai、Xianxiu Xu

  DOI：10.1002/anie.201611024

  日期：2017.2.6

  silver‐catalyzed chemoselective [4+2] annulation of aryl and heteroaryl isocyanides with α‐substituted isocyanoacetamides was developed for the facile and efficient synthesis of 2‐aminoquinolones, naphthyridines, and phenanthrolines. A mechanism for this multistep domino reaction is proposed on the basis of a 13C‐labeling experiment, according to which an unprecedented chemoselective heterodimerization

  开发了一种银催化的芳基和杂芳基异氰化物与α-取代异氰基乙酰胺的化学选择性[4 + 2]环合反应，可轻松高效地合成2-氨基喹诺酮，萘啶和菲咯啉。在13 C标记实验的基础上，提出了这种多步多米诺反应的机制，根据该机制，两种不同的异氰酸酯空前的化学选择性异二聚生成了α-氨基酮亚胺中间体，该中间体经历1,3-氨基迁移形成α -亚氨基酮基烯酮，然后进行6π电环化。
• AZACARBOLINE DERIVATIVES, PREPARATION METHOD THEREOF AND THERAPEUTIC USE OF SAME
  申请人：Arendt Christopher

  公开号：US20110178053A1

  公开（公告）日：2011-07-21

  The invention relates to novel azacarbonlines having formula (I), wherein: R3, R4 represent independently H; hal; CF 3 ; substituted oxy, optionally substituted alkoxy; optionally substituted amino; substituted carbonyl; optionally substituted carboxyl; optionally substituted amide; sulphur, such as optionally substituted sulphones, sulphoxides or sulphides; linear, branched or cyclic C 1 -C 10 alkyl optionally comprising an optionally substituted heteroatom; optionally substituted linear, branched or cyclic C 2 -C 7 alkenyl; optionally substituted linear or branched C 2 -C 6 alkynyl; optionally substituted aryl or heteroaryl; of which may be optionally substituted; in the form of a base or an acid addition salt. The invention also relates to the use of same in therapeutics for the treatment of cancer and to synthesis methods.

  该发明涉及具有以下结构式(I)的新型氮杂碳链化合物，其中：R3，R4分别独立表示H；卤素；CF3；取代的氧基，可选择取代的烷氧基；可选择取代的氨基；取代的羰基；可选择取代的羧基；可选择取代的酰胺基；硫，例如可选择取代的磺酰基、亚砜基或硫醚基；线性、支链或环状的C1-C10烷基，其中可能包含可选择取代的杂原子；可选择取代的线性、支链或环状的C2-C7烯基；可选择取代的线性或支链的C2-C6炔基；可选择取代的芳基或杂芳基；其中可能是可选择取代的；以碱或酸添加盐的形式存在。该发明还涉及在治疗癌症中使用该化合物以及合成方法。
• 2-Cyanophenyl fused heterocyclic compounds, and compositions and uses thereof
  申请人：Wei Zhi-Liang

  公开号：US20080275037A1

  公开（公告）日：2008-11-06

  Fused heterocyclic compounds are provided according to formula 1: where R 1 , R 2 , R 3 , and m are as defined herein. Provided compounds and pharmaceutical compositions thereof are useful for the prevention and treatment of a variety of conditions in mammals including humans, including by way of non-limiting example, pain, inflammation, cognitive disorders, anxiety, depression, and others.

  根据公式1提供了融合的杂环化合物：其中R1、R2、R3和m的定义如本文所述。提供的化合物及其药物组合物对于预防和治疗包括人类在内的哺乳动物的多种疾病状况是有用的，包括但不限于疼痛、炎症、认知障碍、焦虑、抑郁等。
• 2-CYANOPHENYL FUSED HETEROCYCLIC COMPOUNDS, AND COMPOSTIONS AND USES THEREOF
  申请人：WEI Zhi-Liang

  公开号：US20120149700A1

  公开（公告）日：2012-06-14

  Fused heterocyclic compounds are provided according to formula 1: where R 1 , R 2 , R 3 , and m are as defined herein. Provided compounds and pharmaceutical compositions thereof are useful for the prevention and treatment of a variety of conditions in mammals including humans, including by way of non-limiting example, pain, inflammation, cognitive disorders, anxiety, depression, and others.

  提供了按照公式1定义的熔合杂环化合物：其中R1、R2、R3和m如本文所定义。所提供的化合物及其制剂对于哺乳动物，包括人类的多种病症的预防和治疗有用，包括但不限于疼痛、炎症、认知障碍、焦虑、抑郁等。
• Reaction of β-Lactam Carbenes with 2-Pyridyl Isonitriles: A One-Pot Synthesis of 2-Carbonyl-3-(pyridylamino)imidazo[1,2-<i>a</i>]pyridines Useful as Fluorescent Probes for Mercury Ion
  作者：Na Shao、Guang-Xian Pang、Cai-Xia Yan、Gao-Feng Shi、Ying Cheng

  DOI：10.1021/jo201273p

  日期：2011.9.16

  The one-pot reaction of beta-lactam carbenes with 2-pyridyl isonitriles followed by an acidic hydrolysis was reported, which produced 2-carbonyl-3-(pyridylamino)imidazo[1,2-a]pyridines in moderate to good yields. Among the resulting novel imidazo[1,2-a]pyridine derivatives, 1-(6-chloro-3-(5-chloropyridin-2-ylamino)imidazo [1,2-a]pyridin-2-yl)-2-ethylbutan-1-one was demonstrated to be an efficient fluorescent probe for mercury ion both in acetonitrile and in buffered aqueous solution.