(5-Chlor-4-nitro-2-thienyl)-phenylmethanon | 95729-24-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5-Chlor-4-nitro-2-thienyl)-phenylmethanon
• 英文别名: 5-benzoyl-2-chloro-3-nitrothiophene；5-Benzoyl-2-chlor-3-nitrothiophen；(5-chloro-4-nitrothiophen-2-yl)-phenylmethanone
• CAS: 95729-24-1
• 化学式: C₁₁H₆ClNO₃S
• 分子量: 267.693
• InChiKey: WJVFRDOJCRTIBX-UHFFFAOYSA-N

物化性质

• 熔点：
  119-120 °C(Solvent: Ethanol)
• 沸点：
  437.7±45.0 °C(Predicted)
• 密度：
  1.480±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  91.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5-Chlor-4-nitro-2-thienyl)-phenylmethanon 在 ammonium hydroxide 作用下， 以 甲醇 为溶剂， 反应 4.25h， 以64%的产率得到(5-Amino-4-nitro-2-thienyl)-phenylmethanon
  参考文献：
  名称：

  噻吩作为生理活性物质的结构元素，11. Mitt. Substituted thieno [2,3-d] imidazoles 作为潜在的抗病毒剂

  摘要：

  描述了一种新的噻吩并 [2,3-d] 咪唑合成，其中硝基噻吩衍生物与氰氨化二钠在关键序列中反应，所得钠盐在催化氢化后闭环。通过该方法制备的化合物 1，其取代模式对应于苯类似物，Enviroxime (B)，对犀牛和其他小核糖核酸病毒非常有效，显示出比这更低的抗病毒活性。

  DOI：

  10.1002/ardp.19853180110
• 作为产物：
  描述：

  (5-chlorothiophen-2-yl)(phenyl)methanone 在 硫酸 、 硝酸 作用下， 反应 0.5h， 以81%的产率得到(5-Chlor-4-nitro-2-thienyl)-phenylmethanon
  参考文献：
  名称：

  Studien zur Chemie von thienoanellierten O,N- und S,N-haltigen Heterocyclen, 10. Mitt.: Synthese von 2- substituierten Thieno-Diltiazemderivaten

  摘要：

  The syntheses of 2-acetyl-, 2-benzyl-, and 2-ethyl-thieno-diltiazem derivatives are described starting from the corresponding 5-substituted 3-nitro-2-thiophenthiol via reaction with racemic methyl trans-3-(4-methoxyphenyl)-glycidate under different conditions (solvent, catalyst, temperature) to obtain pure three or erythro products. The nitro groups of these products were reduced and the resulting amino esters cyclized. The thieno[2,3-b][1,4]thiazepin-5(4H)-ones were N-alkylated and acetylated in position 3. The desired 2-substituted 4-(2-dimethylaminoethyl)-4,5,6,7-tetrahyro-7-(4-methoxyphenyl)-5-oxothieno[2,3-b][1,4]thiazepin-6-yl acetates were isolated in good yields.

  DOI：

  10.1007/bf00807431

文献信息

• Synthesis of Nitrated Thienylphosphonates via Michaelis-Arbuzov-Type Rearrangement
  作者：Thomas Erker、Norbert Handler

  DOI：10.1055/s-2004-815978

  日期：——

  A facile, catalyst-free synthesis of diethyl thienylphosphonates under mild conditions without solvent is described. The desired products were obtained, via a Michaelis-Arbuzov-type rearrangement, from various activated thienyl halides by reacting with triethyl phosphite.

  本文描述了一种在温和条件下无需溶剂的、简便的无催化剂二乙基噻吩基膦酸酯合成方法。通过米氏-阿尔布佐夫型重排，从各种活化的噻吩基卤化物与亚磷酸三乙酯反应，获得了所需产物。
• Preparation of Thieno[2,3-b]pyrazines as Bioisosteres for Quinoxaline Derivatives wiht Reverse Transcriptase Inhibition
  作者：Thomas Erker、Karin Trinkl

  DOI：10.3987/com-01-9371

  日期：——

  Replacement of the fused aromatic moiety in GW-420867X, a HIV-1 specific nonnucleoside reverse transcriptase inhibitor, with thiophene provided 2-oxo-1,2,3,4-tetrahydrothieno[2,3-b]pyrazine derivatives. The synthesis starts with the reaction of 5-acyl-2-chloro-3-nitrothiophene and different amino acid derivatives. The resulting substitution products are reduced, cyclized and N-acylated to give the desired compounds (27 - 33).
• Synthesis of 1,2,4-Oxadiazolylimidazo[1,5-a]thieno[2,3-e]pyrazines as Ligands for the g-Aminobutyric Acid A/Benzodiazepine Receptor Complex
  作者：Thomas Erker、Karin Trinkl

  DOI：10.3987/com-01-9297

  日期：——

  Starting from 5-benzoyl-2-chloro-3-nitrothiophene the thieno[2,3-b]pyrazine-2,3-dione ring system (4) was synthesized. This compound was reacted with potassium tert-butoxide and diethyl chlorophosphate to give diethyl 7-benzoyl-4-isopropyl-3-oxo-3,4-dihydrothieno[2,3-b]pyrazin-2-ylphosphate (5), which gave with the desired 5-alkyl-3-isocyanomethyl-1,2,4-oxadiazoles in the presence of additional potassium tert-butoxide the 1,2,4-oxadiazolylimidazo[1,5-a]thieno[2,3-e]pyrazine derivatives (6-10) as ligands for the gamma -aminobutyric acid A / benzodiazepine receptor complex.
• Erker, Scientia Pharmaceutica, 1996, vol. 64, # 3-4, p. 345 - 352
  作者：Erker

  DOI：——

  日期：——
• Studies on the Chemistry of Thienoannelated O,N- and S,N-Containing Heterocycles. Part 19[1]: Thieno[2,3-b][1,4]thiazines with Calcium Antagonistic and Potassium Opening Activities
  作者：Thomas Erker、Maria E. Schreder、Christian Studenik

  DOI：10.1002/(sici)1521-4184(200002)333:2/3<58::aid-ardp58>3.0.co;2-l

  日期：2000.2

  In this study novel substituted 6-benzyl-thieno[2,3-b] [1,4]thiazines with an urea moiety were synthesized. Structural modifications of the amino side chain were carried out with the aim of finding tissue specific compounds. The effects on papillary muscles, right atria, aortic strips, and terminal ilea were investigated. Compounds 10c and 10d showed the most potent negative inotropic effect. The calcium antagonism of all derivatives occurred in a non-competitive manner, which may indicate that they also have potassium channel opening activities.