2-(4-Chloro-2-nitrophenoxy)acetyl chloride | 75263-82-0

• 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-(4-Chloro-2-nitrophenoxy)acetyl chloride
• CAS: 75263-82-0
• 化学式: C₈H₅Cl₂NO₄
• 分子量: 250.038
• InChiKey: UFSXXMPKPAJBSC-UHFFFAOYSA-N

物化性质

• 沸点：
  350.3±27.0 °C(Predicted)
• 密度：
  1.541±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-Chloro-2-nitrophenoxy)acetyl chloride 在 吡啶 、 铁粉 、 碳酸氢钠 、 氯化铵 作用下， 以 水 、 丙酮 为溶剂， 反应 14.17h， 生成 N-[4-(aminosulfonyl)-2-methylphenyl]-2-[4-chloro-2-(4-methylbenzenesulfonyl)aminophenoxy]acetamide
  参考文献：
  名称：

  Identification of the novel N-phenylbenzenesulfonamide derivatives as potent HIV inhibitors

  摘要：

  Searching for more safe and effective agents for HIV treatments is still an urgent topic worldwide. Based on our continuous modifications on the benzophenone derivatives as HIV-1 reverse transcriptase (RT) inhibitors, a new template bearing N-phenylbenzenesulfonamide (PBSA) structure was designed to enhance the interactions with HIV-1 RT. In this manuscript, a series of PBSA derivatives were synthesized and evaluated for their anti-HIV-1 activity. The preliminary test showed that these compounds were potent to inhibit wild-type HIV-1 with EC50 values ranging of 0.105-14.531 mu mol/L. In particular, compound 13f not only has high anti-HIV-1 activity (0.108 mu mol/L), but also possesses low toxicity with a TI value of 1816.6. Furthermore, the major interactions of the inhibitor 13f with HIV-1 RT were also investigated using the molecular modelling. Our discovered structure-activity relationships (SARs) of these analogues may serve as an important clue for further optimizations. (C) 2014 Yong-Tang Zheng and Xiao-Dong Ma. Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. All rights reserved.

  DOI：

  10.1016/j.cclet.2014.11.004
• 作为产物：
  描述：

  4-氯-2-硝基苯酚 在 氯化亚砜 、 sodium hydroxide 作用下， 生成 2-(4-Chloro-2-nitrophenoxy)acetyl chloride
  参考文献：
  名称：

  Studies of O,O-Dimethyl α-(2,4-Dichlorophenoxyacetoxy)ethylphosphonate (HW02) as a New Herbicide. 1. Synthesis and Herbicidal Activity of HW02 and Analogues as Novel Inhibitors of Pyruvate Dehydrogenase Complex

  摘要：

  On the basis of the previous work for optimization of O,O-diethyl alpha-(substituted phenoxyacetoxy)alkylphosphonates, further extensive synthetic modifications were made to the substituents in alkylphosphonate and phenoxy moieties of the title compounds. New O,O-dimethyl alpha-(substituted phenoxyacetoxy)alkylphosphonates were synthesized as potential inhibitors of pyruvate dehydorogenase complex (PDHc). Their herbicidal activity and efficacy in vitro against PDHc were examined. Some of these compounds exhibited significant herbicidal activity and were demonstrated to be effective inhibitors of PDHc from three different plants. The structure-activity relationships of these compounds including previously reported analogous compounds were studied by examining their herbicidal activities. Both inhibitory potency against PDHc and herbicidal activity of title compounds could be increased greatly by optimizing substituent groups of the title compounds. O,O-Dimethyl alpha-(2,4-dichlorophenoxyacetoxy)ethylphosphonate (I-5), which acted as a competitive inhibitor of PDHc with much higher inhibitory potency against PDHc from Pisum sativum and Phaseolus radiatus than from Oryza sativa , was found to be the most effective compound against broadleaf weeds and showed potential utility as herbicide.

  DOI：

  10.1021/jf104247w

文献信息

• Synthesis of New Thienopyridine Derivatives by [3+2]- and [2+2]-Cycloaddition Reactions
  作者：Mátyás Milen、György Keglevich、Péter Ábrányi-Balogh、András Dancsó

  DOI：10.1055/s-0032-1316794

  日期：——

  Abstract The reaction of 6,7-dihydrothieno[3,2-c]pyridine derivatives with 1,3-dipoles, such as a nitrile oxides or nitrile imines, gave novel fused heterocycles. The Staudinger reaction of the starting material was also studied. This reaction was stereoselective and exclusively gave racemic cis-cycloadducts in which the thienopyridine core was fused with a β-lactam ring. The reaction of 6,7-dihydrothieno[3

  摘要 6,7-二氢噻吩并[3,2- c ]吡啶衍生物与1,3-偶极，如一氧化氮或腈亚胺的反应，得到了新颖的稠合杂环。还研究了起始材料的斯托丁格反应。该反应是立体选择性的，并且仅产生外消旋的顺式-环加合物，其中噻吩并吡啶核与β-内酰胺环稠合。 6,7-二氢噻吩并[3,2- c ]吡啶衍生物与1,3-偶极，如一氧化氮或腈亚胺的反应，得到了新颖的稠合杂环。还研究了起始材料的斯托丁格反应。该反应是立体选择性的，并且仅产生外消旋的顺式-环加合物，其中噻吩并吡啶核与β-内酰胺环稠合。
• Synthesis, structure–activity relationships, and docking studies of N-phenylarylformamide derivatives (PAFAs) as non-nucleoside HIV reverse transcriptase inhibitors
  作者：Xiao-Dong Ma、Qiu-Qin He、Xuan Zhang、Shi-Qiong Yang、Liu-Meng Yang、Shuang-Xi Gu、Yong-Tang Zheng、Fen-Er Chen、Hui-Fang Dai

  DOI：10.1016/j.ejmech.2012.03.032

  日期：2012.12

  A series of N-phenylarylformamide derivatives (PAFAs) with anti-wild-type HIV-1 activity (EC50 values) ranging from 0.3 nM to 5.1 nM and therapeutic index (TI) ranging from 10 616 to 271 000 were identified as novel non-nucleoside reverse transcriptase inhibitors. Among them, compound 13g (EC50 = 0.30 nM, TI = 184 578), 131 (EC50 = 0.37 nM, TI = 212 819), 13m (EC50 = 0.32 nM, TI = 260 617) and 13r (EC50 = 0.27 nM, TI = 271 000) displayed the highest activity against this type virus nearly as potent as lead compound GW678248. Moreover, all of them were also active to inhibit the double mutant strain A(17) (K103N + Y181C) with EC50 values of 0.29 mu M, 0.14 mu M, 0.10 mu M and 0.27 mu M, respectively. In particular, compound 13m, which showed broad-spectrum anti-HIV activity, was also effective to inhibit the HIV-2 ROD replication within 4.37 mu M concentration. (C) 2012 Elsevier Masson SAS. All rights reserved.
• US4207234A
  申请人：——

  公开号：US4207234A

  公开（公告）日：1980-06-10
• US4472300A
  申请人：——

  公开号：US4472300A

  公开（公告）日：1984-09-18
• US5139564A
  申请人：——

  公开号：US5139564A

  公开（公告）日：1992-08-18