2-amino-5-phenylthiophene-3-carbonitrile | 60271-29-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 2-amino-5-phenylthiophene-3-carbonitrile
• CAS: 60271-29-6
• 化学式: C₁₁H₈N₂S
• mdl: MFCD06803446
• 分子量: 200.264
• InChiKey: WEAZGHUZIQFNLY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 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：
  78
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P330,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,H312,H315,H319,H332,H335
• 储存条件：
  存储条件：2-8°C，避光，惰性气体环境中。

反应信息

• 作为产物：
  描述：

  thiophenacylmalononitrile 在 盐酸 、 溶剂黄146 作用下， 反应 2.0h， 以60%的产率得到2-amino-5-phenylthiophene-3-carbonitrile
  参考文献：
  名称：

  Metwally, Nadia H.; Abdelrazek, F. M., Egyptian Journal of Chemistry, 1999, vol. 42, # 5, p. 491 - 498

  摘要：

  DOI：

文献信息

• Microwave-Assisted Synthesis of 5-Substituted 2-Aminothiophenes Starting from Arylacetaldehydes
  作者：Stéphanie Hesse、Germain Revelant、Sandrine Dunand、Gilbert Kirsch

  DOI：10.1055/s-0030-1261032

  日期：2011.9

  An easy three-step pathway for the synthesis of arylacet­aldehydes from the corresponding carboxylic acids in very high yields is described. Their use as precursors of 5-substituted-2-aminothiophenes is illustrated via a microwave-assisted Gewald reaction. This method allows obtaining the expected compounds in a shorter time and with better yields and purities than the classical procedures.

  一种从相应的羧酸合成高产率芳基乙醛的简单三步骤途径被描述。通过微波辅助的Gewald反应，它们作为5-取代-2-氨基噻吩的前体的用途被阐明。这种方法允许在更短的时间内以更好的产率和纯度获得预期的化合物，优于经典的方法。
• Process for the manufacture of heterocyclic compounds
  申请人：Imperial Chemical Industries Limited

  公开号：US04111956A1

  公开（公告）日：1978-09-05

  Process for manufacture of the heterocyclic compounds of the formula: ##STR1## wherein X is cyano, acyl, alkylsulphonyl, arylsulphonyl, optionally substituted alkoxycarbonyl, nitro, phenyl or sulphamoyl, and Y is hydrogen, optionally substituted alkyl or optionally substituted aryl, which comprises reacting a compound of the formula: ##STR2## with an acid halide in the presence of a compound of the formula ##STR3## and optionally in the presence of an aprotic solvent, and subjecting the resulting compound of the formula: ##STR4## or an acid salt thereof, to hydrolysis in acidic medium, wherein Z is hydrogen or an optionally substituted alkyl or aryl radical, and R.sup.2 and R.sup.3 each independently representing optionally substituted alkyl, cycloalkyl or aryl radicals, or R.sup.2 and R.sup.3 together form with the nitrogen atom a 5- or 6-membered nitrogen-containing heterocyclic ring.

  制造具有以下结构的杂环化合物的方法：##STR1## 其中X是氰基、酰基、烷基磺酰基、芳基磺酰基、可选择取代的烷氧羰基、硝基、苯基或磺酰基，Y是氢、可选择取代的烷基或可选择取代的芳基，包括将具有以下结构的化合物：##STR2## 与酸卤在具有以下结构的化合物的存在下反应##STR3## 可选择在无水溶剂的存在下，并将得到的具有以下结构的化合物：##STR4## 或其酸盐，在酸性介质中水解，其中Z是氢或可选择取代的烷基或芳基基团，R.sup.2和R.sup.3各自独立地表示可选择取代的烷基、环烷基或芳基基团，或R.sup.2和R.sup.3与氮原子一起形成5-或6-成员含氮杂环环。
• NOVEL ANTI-CANCER COMPOUNDS
  申请人：KATHOLIEKE UNIVERSITEIT LEUVEN

  公开号：US20150126559A1

  公开（公告）日：2015-05-07

  The present invention relates to compounds having cytostatic activity against tumor cells. The compounds of the invention are of formula (I), or derivatives hereof, wherein R 0 , R 1 , R 2 , A, and X have defined meanings as described in claim 1 .

  本发明涉及具有抗肿瘤细胞细胞毒活性的化合物。本发明的化合物属于式(I)的化合物，或其衍生物，其中R0、R1、R2、A和X的定义如权利要求书中所述。
• One-Pot Synthesis of 2,3,5-Trisubstituted Thiophenes through Three-Component Assembly of Arylacetaldehydes, Elemental Sulfur, and 1,3-Dicarbonyls
  作者：Zilong Wang、Zhonghua Qu、Fuhong Xiao、Huawen Huang、Guo-Jun Deng

  DOI：10.1002/adsc.201701332

  日期：2018.2.15

  The three‐component reaction for the synthesis of 2‐arylthiophenes has been developed. Easily available arylacetaldehydes, 1,3‐dicarbonyls, and elemental sulfur were directly assembled through cascade condensation/ annulation under base conditions. The present protocol provides a facile entry to 2,3,5‐trisubstituted thiophenes with moderate to excellent yields and good functional group tolerance.

  已经开发了用于合成2-芳基噻吩的三组分反应。容易获得的芳基乙醛，1,3-二羰基和元素硫在碱性条件下通过级联缩合/环合反应直接组装。本协议提供了2,3,5-三取代噻吩的简便入门方法，具有中等至优异的收率和良好的官能团耐受性。
• Cyanothiophenes, their preparation and their use in pharmaceutical compositions
  申请人：Anderskewitz Ralf

  公开号：US20060094764A1

  公开（公告）日：2006-05-04

  The present invention relates to cyanothiophenes of general formula wherein the Rs are defined as in the claims, the tautomers, their stereoisomers, the mixtures thereof and the salts thereof, which have valuable pharmacological properties, particularly a glugacon receptor-antagonistic activity.

  本发明涉及一般式为的氰基噻吩，其中Rs的定义如权利要求中所述，它们的互变异构体、立体异构体、混合物和盐具有有价值的药理特性，特别是一种胰高血糖素受体拮抗活性。