2-cyano-3-(4-chlorophenyl)-prop-2-enethioamide | 39145-33-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-cyano-3-(4-chlorophenyl)-prop-2-enethioamide
• 英文别名: 2-Propenethioamide, 3-(4-chlorophenyl)-2-cyano-；3-(4-chlorophenyl)-2-cyanoprop-2-enethioamide
• CAS: 39145-33-0
• 化学式: C₁₀H₇ClN₂S
• 分子量: 222.698
• InChiKey: RZHHDALLVIGWBS-UHFFFAOYSA-N

物化性质

• 熔点：
  >300 °C(Solv: N,N-dimethylformamide (68-12-2))
• 沸点：
  393.1±52.0 °C(Predicted)
• 密度：
  1.385±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  81.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-cyano-3-(4-chlorophenyl)-prop-2-enethioamide 在 氢氧化钾 、 sodium methylate 、 三乙胺 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 18.0h， 生成 3-Amino-2-carbamoyl-4-(4-chloro-phenyl)-6-oxo-5,6-dihydro-thieno[2,3-b]pyridine-5-carboxylic acid ethyl ester
  参考文献：
  名称：

  REACTIONS OF α-THIOCARBOXAMIDOCINNA-MONITRILE DERIVATIVES WITH DIETHYL MALONATE: SYNTHESIS OF PYRAZOLO-[3,4-b]-α-PYRIDINONE, THIENO[2,3-b]-α-PYRIDINONE, PYRIDO[2,3:4′,5′]THIENO[2,3-c]PYRIDAZINE AND PYRIDO[2,3:4′,5′]-THIENO[2,3-d]PYRIMIDINONETHIONE DERIVATIVES

  摘要：

  3-Cyano-4-aryl-5-ethoxycarbonyl-6-pyridinone-2-thione derivatives 3a-c reacted with several halogen-containing compounds to give the corresponding 2-S-methylpyridinones 4a-c, 2-S-acetonyl pyridinones 7a-c, 2-S-benzoyl methyl pyridinones 12a-c, 2-S-acetamidopyridinones 15a-c and 2-S-ethoxycarbonyl methylpyridinones 20a-c. The ethanolic solution of KOH used as a cyclization agent to give the corresponding thieno[2,3-b]pyridines 8a-c, 13a-c, 16a-c and 21a-c. Hydrazine hydrate, nitrous acid, carbon disulphide, acetic anhydride, formic acid, acetic acid and acetyl acetone gave further cyclization to construct an additional ring.

  DOI：

  10.1080/10426509708031587
• 作为产物：
  描述：

  6-amino-2,4-bis-(4-chloro-phenyl)-3,5-dicyano-3,4-dihydro-2H-thiopyran-3-carbothioic acid amide 以 氘代二甲亚砜 为溶剂， 反应 48.0h， 生成 2-cyano-3-(4-chlorophenyl)-prop-2-enethioamide
  参考文献：
  名称：

  Brunskill, John S. A.; De, Asish; Ewing, David F., Journal of the Chemical Society. Perkin transactions II, 1980, p. 4 - 7

  摘要：

  DOI：

文献信息

• Some Reactions of 2-Functionalized 3-Amino-4-aryl-6-(2′-thienyl)-thieno[2,3-b]pyridines: Synthesis of New Pyridothienopyrimidines, Pyridothienotriazines and Related Fused Tetracyclic Systems
  作者：A. E. Abdel-Rahman、E. A. Bakhite、O. S. Mohamed、E. A. Thabet

  DOI：10.1080/10426500307820

  日期：2003.1.1

  4-Aryl-3-cyano-6-(2'-thienyl)-pyridine-2(1 H )-thiones ( 2a-c ) were prepared and reacted with chloroacetonitrile or chloroacetamide to furnish 3-amino-4-aryl-6-(2'-thienyl)-thieno[2,3-b]pyridine-2-carbonitriles ( 4a-c ) and 2-carboxamide analogs 6a-c respectively. The reaction of 4a and 6a-c with a variety of reagents namely, formamide, carbon disulfide, phenyl isothiocyanate, ethylene diamine, sodium

  制备 4-Aryl-3-cyano-6-(2'-thienyl)-pyridine-2(1 H)-thiones (2a-c) 并与氯乙腈或氯乙酰胺反应得到 3-amino-4-aryl-6 -(2'-噻吩基)-噻吩并[2,3-b]吡啶-2-甲腈(4a-c)和2-甲酰胺类似物分别为6a-c。4a 和 6a-c 与多种试剂即甲酰胺、二硫化碳、异硫氰酸苯酯、乙二胺、叠氮化钠、原甲酸三乙酯和亚硝酸反应，并对其产物进行了鉴定。大多数这些产物进行进一步反应以获得其余的标题化合物。
• REACTIONS WITH HYDRAZONOYL HALIDES XIX¹: SYNTHESIS OF SOME PYRAZOLE AND 5-ARYLAZOTHIAZOLE DERIVATIVES
  作者：Hussein F. Zohdi、Nora M. Rateb、Abdou O. Abdelhamid

  DOI：10.1080/10426509808032458

  日期：1998.1

  Abstract Hydrazonoyl chlorides 1 reacted with 2-aryl-1-cyano-1-thiazol-2-ylethenes 2 in presence of triethyl-amine to give the cycloadducts 4. which were converted to the corresponding pyrazoles 5 by the action of sodium methoxide. The reaction of hydrazonoyl halides 1 and 6 with each of 2-aryli-dene-2-cyanoethanethioamides 7 and 2-arylhydrazono-2-cyanoethanethioamides 14 in ethanolic tri-ethylamine

  摘要 在三乙胺的存在下，腙酰氯 1 与 2-芳基-1-氰基-1-噻唑-2-亚乙基 2 反应生成环加合物 4，在甲醇钠的作用下将其转化为相应的吡唑 5。已经研究了腙酰卤 1 和 6 与 2-芳基-dene-2-氰基乙硫酰胺 7 和 2-芳基腙-2-氰基乙硫酰胺 14 在乙醇三乙胺或氢氧化钠乙醇溶液中的反应。所有产品的结构都是基于它们的光谱数据和替代合成建立的。
• <i>N</i>-1-Naphthyl-3-oxobutanamide in Heterocyclic Synthesis: A Facile Synthesis of Nicotinamide, Thieno[2,3-<i>b</i>]pyridine, and Bi- or Tricyclic Annulated Pyridine Derivatives Containing Naphthyl Moiety
  作者：Abdel Haleem M. Hussein、Mohamed A. M. Gad-Elkareem、Abu-Bakr A. A. M. El-Adasy、Ismail M. Othman

  DOI：10.1080/10426500802453658

  日期：2009.9.18

  to Curtius rearrangement in boiling xylene to give imidazothienopyridine 20. Reaction of 10 with either formic acid or triethylorthoformate and phenyl isothiocyanate gave the corresponding pyridothienotriazepines 22 and 23, respectively. The interaction of 10 with acetylacetone furnished the pyrazolyl derivative 24. The structures of the synthesized compounds were established from their analytical and

  N-1-Naphthyl-3-oxobutanamide (1) 与芳基氰基硫代乙酰胺 2a-c 在乙醇/哌啶溶液中回流反应生成吡啶-2(1H)-硫酮 6a-c。化合物 6a 与 α-卤代酮 7a-e 反应生成 6-硫代-N-1-萘基-烟酰胺衍生物 8a-e，其环化为噻吩并 [2,3-b] 吡啶衍生物 9a-e。化合物9a与水合肼和甲酰胺的反应分别得到噻吩并[2,3-b]吡啶碳酰肼衍生物10和吡啶并噻吩并嘧啶衍生物11。9a与异硫氰酸苯甲酰酯反应得到硫脲衍生物12。化合物12在用醇NaOH处理后得到吡啶并噻吩并嘧啶13。9a的皂化得到氨基酸15，当在Ac 2 O中回流时得到16。用 AcONH4/AcOH 处理化合物 16 得到 17。9b 的重氮化和自偶联得到吡啶并噻吩并三嗪 18。此外，邻氨基酰肼 10 的重氮化得到相应的叠氮化物 19，将其在沸腾的二甲苯中进行 Curtius 重排得到咪唑并噻吩并吡啶
• Novel dihydropyridine thioglycosides and their corresponding dehydrogenated forms as potent anti-hepatocellular carcinoma agents
  作者：Galal H. Elgemeie、Dina H. El-Naggar

  DOI：10.1080/15257770.2018.1457161

  日期：2018.4.3

  preparation of a new class of dihydropyridine thioglycosides and their corresponding dehydrogenated forms, via reaction of piperidinium salts of dihydropyridinethiones with 2,3,4,6-tetra-O-acetyl-α-D-gluco- and galactopyranosyl bromides has been studied. The evaluation of antiproliferative activity against HepG-2 cell lines (liver carcinoma cell lines) of the dihydropyridine thioglycosides and pyridine

  摘要 通过二氢吡啶硫酮的哌啶鎓盐与 2,3,4,6-四-O-乙酰基-α-D-葡糖-和吡喃半乳糖基溴反应制备一类新的二氢吡啶硫糖苷及其相应的脱氢形式的新方法已被研究。二氢吡啶硫糖苷和吡啶硫糖苷对 HepG-2 细胞系（肝癌细胞系）的抗增殖活性的评估表明，许多硫糖苷具有有趣的抗肿瘤活性，特别是 5c、5g、5l、5o、5p、7a、7i、7p 、8b、8f、8s 和 8v。
• New Multicomponent Synthesis of Functionalized Nitriles and Esters of 6-Alkylsulfanyl-1,4-dihydronicotinic Acids
  作者：I. N. Kalashnik、V. D. Dyachenko

  DOI：10.1134/s1070363220030068

  日期：2020.3

  AbstractThe multicomponent condensation of malononitrile, hydrogen sulfide, aryl or hetaryl aldehydes, 1,3-dicarbonyl compounds and alkylating reagents afforded functionalized nitriles and esters of 6-alkylsulfanyl-1,4-dihydronicotinic acids, their aromatic analogues and 1,4-dihydrothieno[2,3-b]pyridines.

  摘要丙二腈，硫化氢，芳基或杂芳基醛，1,3-二羰基化合物和烷基化试剂的多组分缩合可提供官能化的腈和6-烷基硫烷基-1,4-二氢烟酸的酯，它们的芳香族类似物和1,4-二氢噻吩并[ 2,3- b ]吡啶。