2-氯-1-甲基-3,5-二硝基苯 | 18905-50-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-氯-1-甲基-3,5-二硝基苯
• 英文名称: 2-chloro-1-methyl-3,5-dinitrobenzene
• 英文别名: 1-chloro-2-methyl-4,6-dinitrobenzene；2-methyl-4,6-dinitrochlorobenzene；2,6-dichloro-4-nitroaniline；2-chloro-3,5-dinitrotoluene；2-chloro-1-methyl-3,5-dinitro-benzene；2-chloro-3,5-dinitro-toluene
• CAS: 18905-50-5
• 化学式: C₇H₅ClN₂O₄
• mdl: MFCD00460854
• 分子量: 216.581
• InChiKey: FXMUNKFQIKDUBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  91.6
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2904909090

反应信息

• 作为反应物：
  描述：

  2-氯-1-甲基-3,5-二硝基苯 在 吡啶 、 potassium carbonate 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 生成 [5,5-dimethyl-2-(2-methyl-4,6-dinitrophenyl)-3-oxocyclohexen-1-yl] 2,2-dimethylpropanoate
  参考文献：
  名称：

  DE2813341

  摘要：

  公开号：
• 作为产物：
  描述：

  2-甲基-4,6-二硝基苯甲醚 在 三氧化二氮 、 乙醇 、 氨 、 硝酸 作用下， 生成 2-氯-1-甲基-3,5-二硝基苯
  参考文献：
  名称：

  Koerner; Contardi, Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1915, vol. <5> 24 I, p. 891

  摘要：

  DOI：

文献信息

• Steric Effects in Nucleophilic Aromatic Substitution reactions with aromatic amines 12th communication on nucleophilic aromatic substitution reactions
  作者：Walter Eggimann、Peter Schmid、Heinrich Zollinger

  DOI：10.1002/hlca.19750580132

  日期：——

  of over 20 000. The reaction of aniline with 4-X-2,6-dinitrochlorobenzenes is subject to considerably larger para-substituent effects than the corresponding reactions with N-methylaniline. These results are interpreted in terms of two effects: (i) A primary steric effect, which renders the approach of N-methylaniline to the substrate difficult. (ii) A shift towards earlier, more reactant-like transition

  苯胺和N-甲基苯胺与各种取代的硝基氯苯在乙腈中的S N Ar反应动力学表明，中间体σ-络合物的形成决定了速率。苯胺和N-甲基苯胺反应的速率常数之比（k A / k M）随着6位取代基尺寸的增加而增加。用苦基氯ķ甲/ ķ中号达到的超过一个值20000 。苯胺与4-X-2,6- dinitrochlorobenzenes反应受到相当大的第-取代基的作用要比与N-甲基苯胺的相应反应要大。这些结果可以用两种效应来解释：（i）主要的空间效应，这使N-甲基苯胺难以接近底物。（ii）由主要的空间效应引起的向更早的，更像反应物的过渡态结构的转变。在早期过渡态中，预计衬底中吸电子替代物的活化能力相对较小。缓慢的N-甲基苯胺反应的早期过渡态和快速苯胺反应的晚期过渡态明显与基于Hammond假设的预期相矛盾。
• Preparation of Substituted Methyl o-Nitrophenyl Sulfides
  作者：Katerina Dudova、Frantisek Castek、Vladimir Machacek、Petr Simunek

  DOI：10.3390/70100007

  日期：——

  their 1H- and 13C-NMR spectra. The base catalysed ring closure of methyl 2-(methoxycarbonylmethylsulfanyl)-3,5-dinitrobenzenecarboxylate only results in an attack of carbanion on the ester group, not on a nitro group as with the other compounds prepared. The cyclisation product is methyl 3-hydroxy-5,7-dinitro-benzo[b]thiophene-2-carboxylate (11).

  在三乙胺或吡啶的催化下，取代的邻硝基氯苯与取代的甲硫醇的亲核取代已被用于制备一系列适当取代的甲基-邻硝基苯硫醚。制备的化合物通过它们的 1H-和 13C-NMR 谱进行鉴定。2-(甲氧基羰基甲基硫烷基)-3,5-二硝基苯甲酸甲酯的碱催化闭环仅导致碳负离子对酯基的攻击，而不像制备的其他化合物那样对硝基进行攻击。环化产物是 3-羟基-5,7-二硝基-苯并[b]噻吩-2-羧酸甲酯 (11)。
• Oxime ethers and pesticidal preparations containing them
  申请人：Ciba-Geigy AG

  公开号：US03941839A1

  公开（公告）日：1976-03-02

  New oxime ethers and pesticidal and herbicidal preparations containing them are disclosed. The oxime ethers correspond to the formula ##SPC1## Wherein R.sub.1 is a hydrogen atom or a lower alkyl radical; R.sub.2 is an aliphatic, cycloaliphatic, araliphatic, aromatic or heterocyclic radical; or wherein R.sub.1 and R.sub.2 form part of a saturated or unsaturated carbocycle or a 5-, 6- or 7-membered heterocycle; R.sub.3 is a nitro, trifluoromethyl, formyl, lower carbalkoxy, sulfamyl or mono- or di-lower alkyl sulfamyl radical; R.sub.4.sub.- and R.sub.5.sub.- each is a hydrogen or halogen atom, an amino, mono- or di-lower alkyl amino, lower alkoxy, cycloalkoxy, lower alkylthio, nitro, lower carbalkoxy, arylthio, lower aralkylthio or lower alkyl group, or 5-, 6- or 7-membered heterocycle.

  揭示了新的肟醚化合物和含有它们的杀虫剂和除草剂制剂。这些肟醚化合物对应于以下结构式：其中R1为氢原子或较低的烷基基团；R2为脂肪族、环脂肪族、芳基脂肪族、芳香族或杂环基团；或者R1和R2构成饱和或不饱和的碳环或5、6或7元杂环的一部分；R3为硝基、三氟甲基、甲酰基、较低的羰基烷氧基、磺胺基或单或双较低的烷基磺胺基基团；R4和R5分别为氢或卤素原子、氨基、单或双较低的烷基氨基、较低的烷氧基、环烷氧基、较低的烷基硫氧基、硝基、较低的羰基烷氧基、芳基硫氧基、较低的芳基烷基硫氧基或较低的烷基基团，或者为5、6或7元杂环。
• 2-Anilino-1.3.4-thiadiazole, Hemmstoffe der oxidativen und photosynthetischen Phosphorylierung
  作者：G. Schäfer、A. Trebst、K. H. Büchel

  DOI：10.1515/znc-1975-3-408

  日期：1975.4.1

  2-anilino-1,3,4-thiadiazoles carrying various substituents in the 5-position as well as in the benzene-ring were synthesized.

  The compounds were tested with rat-liver-mitochondria and with spinach-chloroplasts and revealed to be potent uncouplers of both, oxidative and photosynthetic phosphorylation, with p I₅₀-values rangeing from 6.79 to 4.05. At higher concentration all compounds are inhibitors of the Hillreaction.

  In mitochondria a fair correlation exists between pKa of the acidic NH-group and the uncoupling activity; a maximum is obtained around pKa= 6 .8 , whereas in chloroplasts activity is shifted to more acid pKa-values.

  The compounds meet the requirements for uncouplers according to the chemi-osmotic theory, being lipophilic weak acids. N-methylation causes total loss of activity in mitochondrial oxidative phosphorylation.

  The inhibitory action on photosynthetic electron transport is located within photosystem II. This latter activity is almost independent of substituent effects in contrast to uncoupling of either respiratory- or photo-phosphorylation

  摘要：合成了带有各种取代基的5-位置和苯环的2-苯胺基-1,3,4-噻二唑类化合物。这些化合物经过大鼠肝线粒体和菠菜叶绿体的测试，显示为氧化和光合磷酸化的有效解耦剂，其p I50 值范围为6.79至4.05。在较高浓度下，所有化合物均为Hill反应的抑制剂。在线粒体中，酸性NH基团的pKa值与解耦活性之间存在较好的相关性；最大值约为pKa=6.8，而在叶绿体中，活性向更酸性的pKa值转移。这些化合物符合根据化学渗透理论对解耦剂的要求，是亲脂性弱酸。N-甲基化导致线粒体氧化磷酸化活性完全丧失。对光合电子传递的抑制作用位于光系统II内。与解耦呼吸或光合磷酸化相比，后者的活性几乎不受取代基效应的影响。
• SUBSTITUTE DIPHENYLAMINE COMPOUNDS USE THEREOF AS ANTITUMOR AGENTS
  申请人：SINOCHEM CORPORATION

  公开号：US20150011628A1

  公开（公告）日：2015-01-08

  The invention relates to substituted diphenylamine compounds using as antitumor agents. The structure of the compounds is represented as the general formula (I): The groups are as defined as specification. The compound represented by formula (I) showed potent antitumor activity, especially to cure or alleviate the cancer causing by cancer cells of human tissue or organ. The preferred cancers are: colon cancer, liver cancer, lymph cancer, lung cancer, esophageal cancer, breast cancer, central nervous system cancer, melanoma, ovarian cancer, cervical cancer, renal cancer, leukemia, prostatic cancer, pancreatic cancer, bladder cancer, rectal cancer, osteosarcoma, nasopharynx cancer or stomach cancer.

  该发明涉及以取代二苯胺化合物作为抗肿瘤药剂。化合物的结构表示为通式(I)：其中各个基团如规范所定义。由通式(I)表示的化合物显示出强效的抗肿瘤活性，特别是用于治疗或缓解由人体组织或器官的癌细胞引起的癌症。首选的癌症包括：结肠癌、肝癌、淋巴癌、肺癌、食管癌、乳腺癌、中枢神经系统癌、黑色素瘤、卵巢癌、宫颈癌、肾癌、白血病、前列腺癌、胰腺癌、膀胱癌、直肠癌、骨肉瘤、鼻咽癌或胃癌。