2-(苯并[d]噻唑-2-基)-4-氯-3-氧代丁腈 | 160148-12-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 中文名称: 2-(苯并[d]噻唑-2-基)-4-氯-3-氧代丁腈
• 英文名称: 2-(benzo[d]thiazol-2-yl)-4-chloro-3-oxobutanenitrile
• 英文别名: 2-(benzo[d]thiazol-2-yl)-4-chloro-3-oxobutyronitrile；2-(benzo[d]thiazol-2-yl)-4-chloro-3-oxobutanitrile；2-(benzothiazol-2-yl)-4-chloro-3-oxobutanenitrile；2-(2-benzothiazolyl)-4-chloro-3-oxobutyronitrile；2-benzothiazolyl-3-keto-4-chlorobutyronitrile；1-(2-benzothiazolyl)-1-cyano-3-chloroacetone；2-(1,3-Benzothiazol-2-yl)-4-chloro-3-oxobutanenitrile
• CAS: 160148-12-9
• 化学式: C₁₁H₇ClN₂OS
• mdl: MFCD02253671
• 分子量: 250.708
• InChiKey: IMHFEMYVEUVYET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  82
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(苯并[d]噻唑-2-基)-4-氯-3-氧代丁腈 在 肼 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以85%的产率得到1,2-diamino-3-(2-benzothiazolyl)-4(5H)-ketopyrrole
  参考文献：
  名称：

  Novel 3d-metal complexes with 1,2-diamino-3-(2-benzothiazolyl)-4(5H)-ketopyrrole: Synthesis, spectroscopic and structural investigations

  摘要：

  A series of new 3d-metal complexes have been prepared by the reaction of M(CH(3)COO)(2) (M Zn(II), Co(II), Ni(II)) and 1,2-diamino-3-(2-benzothiazolyl)-4(5H)-ketopyrrole (HL) in a methanol (3) or a methanol/dmf (1, 2) medium. All the complexes have been studied by elemental analyses, electronic and IR spectroscopies. The zinc(II) complex 1 and the ligand HL have been investigated using the method of (1)H NMR-spectroscopy at various temperatures. The disappearance of the signal from one proton of the amino group H(5) in the spectrum of complex 1 confirmed the existence of the ligand in the deprotonated form. According to the data of the (1)H NMR-spectroscopy, the ligand HL is coordinated to zinc(II) through the nitrogen atom of the deprotonated amino group and the nitrogen atom of the benzothiazole substituent. These data are in agreement with X-ray structural studies for the ligand HL and the zinc(II) complex 1. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2010.01.015
• 作为产物：
  描述：

  苯并噻唑-2-乙腈 、 氯乙酰氯 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 0.17h， 以96%的产率得到2-(苯并[d]噻唑-2-基)-4-氯-3-氧代丁腈
  参考文献：
  名称：

  有机合成中的腈类：合成一些含有苯并噻唑部分的杂环的便捷途径

  摘要：

  2-(Benzo[d]thiazol-2-yl)-4-chloro-3-oxobutanenitrile (2) 用于合成几种新的苯并噻唑衍生物。化合物 2 与苯胺、水合肼、乙醇胺和甘氨酸乙酯盐酸盐反应，分别生成苯并噻唑衍生物 3-6。

  DOI：

  10.1080/10426500500542828

文献信息

• Synthesis of Some New 1,2,3,4-Tetrahydropyrimidine-2-thione and Their Thiazolo[3,2-<i>a</i>]pyrimidine, Thiazino and Benzothiazepine Derivatives
  作者：A. A. Fadda、S. B. Bondock、A. M. Khalil、Eman H. Tawfik

  DOI：10.1002/jhet.1573

  日期：2013.7

  intermediate for the synthesis of new 1,2,3,4‐tetrahydropyrimidine‐2‐thione and their thiazolo[3,2‐a]pyrimidine, thiazino and benzothiazipen derivatives. The reaction of 4 with haloketones in ethanol catalyzed by base afforded the corresponding thiophenopyrimidine and pyrimidothiazipine derivatives 5, 6, 7, 8, 9, 10. Methylation and formylation of 4 led to the pyrimidine derivatives 15 and 16, respectively

  起始的N-（2-吡啶基）-6-甲基-4-苯基-2-硫代-1,2,3,4-四氢嘧啶-5-羧酰胺（4）被用作合成新的1的关键中间体，2,3,4-四氢嘧啶-2-硫酮及其噻唑并[3,2- a ]嘧啶，噻嗪和苯并噻嗪衍生物。的反应4与由所提供的相应thiophenopyrimidine和pyrimidothiazipine衍生物碱催化的乙醇卤代酮5，6，7，8，9，10。4的甲基化和甲酰化反应生成嘧啶衍生物15和16， 分别。预防性化合物是根据元素和光谱数据建立的。
• Synthesis and Antioxidant Evaluation of Some New Pyrazolopyridine Derivatives
  作者：Moustafa A. Gouda

  DOI：10.1002/ardp.201100171

  日期：2012.2

  azole‐4‐carbaldehyde (28) to afford pyrazolo[3,4‐a]pyrimidines 19–21, 23, 29a, 29b and 30, respectively. Also, the pyrazolopyrimidinone 33 was obtained via treatment of 1 with 1‐cyanoacetyl‐3,5‐dimethylpyrazole (31) followed by cyclization of the formed intermediate 32 with glacial acetic acid. Finally, treatment of 1 with o‐terephthalaldehyde in glacial acetic acid afforded diazepine 34. The newly

  4,6-二甲基-1H-吡唑并[3,4-b]吡啶-3-胺(1)在与3-(2-溴乙酰基)-相互作用时用作合成咪唑并吡唑衍生物7-11的关键中间体2H-chromen-2-one (2), 2-(benzothiazol-2-yl)-4-chloro-3-oxobutanenitrile (3), 2,3-dibromonaphthalene-1,4-dione (4), 石脑油[2 ,3-b]oxirene-2,7-dione (5), 2,5-dichloro-3,6-dihydroxyhexa-2,5-diene-1,4-dione (6), 分别。11 乙酰化得到双乙酰基 12。此外，咪唑并嘧啶 15 是通过在 DMF 中用 3,4-二氧代-3,4-二氢萘-1-磺酸钠 (13) 处理 1，然后将双-吡唑并嘧啶 14 与冰醋酸。另一方面，化合物 1 与 (E)-1-(4-甲氧基苯基)-5-
• Synthesis, DFT Study, and Antitumor Activity of Some New Heterocyclic Compounds Incorporating Isoxazole Moiety
  作者：Wafaa S. Hamama、Mona E. Ibrahim、Hanafi H. Zoorob

  DOI：10.1002/jccs.201700064

  日期：2017.10

  chloroacetamide derivative 2 with NH4SCN.The condensation of 3 with p‐anisaldehyde afforded the corresponding arylidene derivative 4. Also, the alkylation of chloroacetamide derivative 2 with different heterocyclic compounds was investigated. Annulation of 5‐amino‐3‐methylisoxazole (1) with α‐halocarbonyl compounds 12 and 14 furnished pyrrolo[3,2‐d]isoxazole and isoxazolo[5,4‐b]azepin‐6‐one derivatives

  噻唑烷-4-酮衍生物3是由氯乙酰胺衍生物的合成转化2与NH 4的SCN.The缩合3与p -anisaldehyde，得到相应的亚芳基衍生物4。另外，研究了氯乙酰胺衍生物2与不同杂环化合物的烷基化。5-氨基-3-甲基异恶唑（环的1）用α-卤代化合物12和14布置吡咯并[3,2-d]异恶唑和异恶唑并[5,4-b]氮杂-6-酮衍生物13和15分别，而反应1用1-氯-4-（氯甲基）苯制得单烷基化产物17。筛选了新合成的化合物的抗肿瘤活性，并且几何优化与实验观察到的数据非常吻合。
• Synthesis of Some New Pyridine and Pyrimidine Derivatives Containing Benzothiazole Moiety
  作者：Khaled S. Mohamed、Nayra M. Abdulaziz、Ahmed A. Fadda

  DOI：10.1002/jhet.1672

  日期：2013.5

  A variety of pyridine and pyrimidine rings incorporating benzothiazole moiety were synthesized by reaction of 1‐(2‐benzothiazolyl)‐1‐cyano‐3‐chloroacetone (1) with 2‐pyridone, 2‐thioxopyridine, thiouracil, and 2‐thioxopyrimidine derivatives to give compounds 7,9‐dimethylfuro[2,3‐b:4,5‐b′]dipyridin‐4‐ol 5, 4, 6‐diphenylthieno[2,3‐b]pyridin‐2‐yl 9, 2‐(benzo[d]thiazol‐2‐yl)‐2‐(7‐substituted‐5‐oxo‐5H‐thiazolo[3

  通过将1-（2-苯并噻唑基）-1-氰基-3-氯丙酮（1）与2-吡啶酮，2-噻吩并吡啶，硫氧嘧啶和2-噻吩并嘧啶衍生物反应生成多种掺入苯并噻唑部分的吡啶和嘧啶环产生化合物7,9-二甲基呋喃并[2,3- b：4,5- b ']二吡啶-4-醇5，4,6-diphenylthieno [2,3- b ]吡啶-2-基9，2-（苯并[ d ]噻唑-2-基）-2-（7-取代-5-氧代-5 H-噻唑并[3,2 - a ]嘧啶-3-基）乙腈12a和12b，嘧啶基[2,1- b ] [1,3]噻氮平-3-羧酰胺15，和苯并[4,5]噻唑洛[3,2 – b ]哒嗪-3-1 20。
• Synthesis of New Heterocyclic Rings Containing Benzothiazole Moiety
  作者：Khaled S. Mohamed、N. M. Abdulaziz、A. A. Fadda

  DOI：10.1002/jhet.1685

  日期：2013.5

  A variety of heterocylic rings incorporating benzothiazole moiety were synthesized by reaction of 1‐(2‐benzothiazolyl)‐1‐cyano‐3‐chloroacetone 1 with salicylaldehyde, o‐aminothiophenol, 2‐aminothiazole, 2‐aminobenzothiazole, 2‐aminobenzimidazole, alcoholic KOH, and sodium sulfide to give compounds 2, 5, 6, 7, 8, 9, 12, and 14, respectively.

  1-（2-苯并噻唑基）-1-氰基-3-氯丙酮1与水杨醛，邻氨基苯硫酚，2-氨基噻唑，2-氨基苯并噻唑，2-氨基苯并咪唑，醇性KOH的反应合成了各种带有苯并噻唑部分的杂环，和硫化钠，得到化合物2，5，6，7，8，9，12，和14，分别。