methyl (2,4-dinitrophenylsulphanyl)ethanoate | 4871-30-1

• 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: methyl (2,4-dinitrophenylsulphanyl)ethanoate
• 英文别名: (2,4-dinitro-phenylsulfanyl)-acetic acid methyl ester；(2,4-Dinitro-phenylmercapto)-essigsaeure-methylester；Methyl 2-(2,4-dinitrophenylthio)acetate；methyl 2-(2,4-dinitrophenyl)sulfanylacetate
• CAS: 4871-30-1
• 化学式: C₉H₈N₂O₆S
• 分子量: 272.238
• InChiKey: JYKFTRPWOJQMRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  143
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl (2,4-dinitrophenylsulphanyl)ethanoate 在 potassium permanganate 、 溶剂黄146 作用下， 生成 (2,4-dinitro-benzenesulfonyl)-acetic acid methyl ester
  参考文献：
  名称：

  2,4-Dinitrothiophenol as a Reagent for the Characterization of Organic Halogen Compounds

  摘要：

  DOI：

  10.1021/ja01149a019
• 作为产物：
  描述：

  1-氯-2,4-二硝基苯 在 盐酸 、 乙醇 、 sodium acetate 作用下， 生成 methyl (2,4-dinitrophenylsulphanyl)ethanoate
  参考文献：
  名称：

  Friedlaender; Chwala; Slubek, Monatshefte fur Chemie, 1907, vol. 28, p. 275

  摘要：

  DOI：

文献信息

• Organic sulfur compounds. V. The preparation of some benzothiazine hydroxamic acids
  作者：R. T. Coutts、Elizabeth M. Smith

  DOI：10.1139/v67-162

  日期：1967.5.1

  compounds of general structure V with sodium borohydride and palladium–charcoal. These precursors (V) were obtained by reacting methyl (o-nitrophenylthio)acetate and its simple derivatives with a variety of aryl aldehydes, in the presence of piperidine. Attempts to prepare the sulfones of V in a similar manner from methyl or ethyl (o-nitrobenzenesulfonyl)acetate were successful in two instances when

  2-亚芳基-3,4-二氢-4-羟基-3-氧代-2H-1,4-苯并噻嗪异羟肟酸（VI）最好通过还原α-（邻硝基苯硫基）肉桂酸酯和一般的相关化合物来制备。结构 V 与硼氢化钠和钯-木炭。这些前体 (V) 是通过（邻硝基苯硫基）乙酸甲酯及其简单衍生物与多种芳基醛在哌啶存在下反应获得的。当以无水甲醇或乙醇为溶剂时，尝试以类似方式从（邻硝基苯磺酰基）乙酸甲酯或乙酯制备 V 的砜在两种情况下是成功的。另一种反应，其中一分子醛与两分子（邻硝基苯磺酰基）乙酸酯缩合。(2-硝基苯磺酰基)乙酸甲酯和乙酯及其简单的环取代衍生物通过加热乙酸在含有哌啶的水溶液中的溶液顺利水解和脱羧。甲基对硝基苯砜同样...
• ORGANIC SULFUR COMPOUNDS: PART I. BENZOTHIAZINE HYDROXAMIC ACIDS AND RELATED COMPOUNDS
  作者：R. T. Coutts、H. W. Peel、Elizabeth M. Smith

  DOI：10.1139/v65-449

  日期：1965.12.1

  2H-1,4-Benzothiazine hydroxamic acids of type V (see Table I) are readily prepared by reducing suitably substituted (o-nitrophenylthio)acetates (II, R″ = Me or Et) by means of sodium borohydride and palladium–charcoal. The ester precursors can be prepared by the interaction of o-nitrothiophenols and α-bromoesters, but such a method is limited in scope. Diethyl bromomalonate, for example, reacts atypically

  V 型 2H-1,4-苯并噻嗪异羟肟酸（见表 I）可通过硼氢化钠和钯-木炭还原适当取代的（邻硝基苯硫基）乙酸盐（II，R″ = Me 或 Et）来制备。酯前体可以通过邻硝基苯硫酚和α-溴酯的相互作用来制备，但这种方法的范围有限。例如，溴丙二酸二乙酯与邻硝基苯硫酚的反应异常。酯前体通过相应酸的 Fischer-Speier 酯化 (II, R" = H) 更好地制备，而这些酸又是 α-巯基酸对合适的邻氯-（或溴-）硝基苯进行亲核攻击的产物. 这种通用的制备方法在两种情况下都失败了。邻氯硝基苯或4-氯-3-硝基甲苯与α-巯基异丁酸反应时，
• Kinetics of Cyclization of Methyl S-(2,4,6-Trinitrophenyl)mercaptoacetate to 2-Methoxycarbonyl-5,7-dinitrobenzo[d]thiazol-3-oxide
  作者：Marek Janík、Vladimír Macháček、Oldřich Pytela

  DOI：10.1135/cccc19971429

  日期：——

  The cyclization kinetics of methyl S-(2,4,6-trinitrophenyl)mercaptoacetate to 2-methoxycarbonyl-5,7-dinitrobenzo[d]thiazol-3-oxide have been studied in acetate, methoxyacetate or N-methylmorpholine buffers. In the acetate and methoxyacetate buffers, the cyclization obeys the rate equation v = [SH](k'_MeO[CH₃O^-] + k'_B[B^-] + k'_B,MeO[B^-][CH₃O^-]) and goes by two reaction paths differing in the order of their reaction steps, the splitting off of the proton from C-H group being the rate-limiting step in either path. In the N-methylmorpholine buffers, increasing concentration of the base results in gradual decrease of reaction order in the base and change in the rate-limiting step of cyclization. Methyl S-(2,4-dinitrophenyl)mercaptoacetate undergoes cyclization neither in the given buffers nor in methoxide solution.

  研究了在醋酸、甲氧醋酸或N-甲基吗啡缓冲液中，甲基S-(2,4,6-三硝基苯基)硫代乙酸酯环化为2-甲氧羰基-5,7-二硝基苯并[d]噻唑-3-氧化物的动力学。在醋酸和甲氧醋酸缓冲液中，环化遵循速率方程v=[SH](k'MeO[CH3O-]+k'B[B-]+k'B,MeO[B-][CH3O-])，并通过两种反应途径进行，其反应步骤的顺序不同，C-H基团的质子分裂是任一途径的速率限制步骤。在N-甲基吗啡缓冲液中，碱的浓度增加导致反应阶数逐渐降低，并改变环化的速率限制步骤。甲基S-(2,4-二硝基苯基)硫代乙酸酯在给定的缓冲液和甲氧基溶液中均不会发生环化。
• Wagner,K. et al., Chemische Berichte, 1973, vol. 106, p. 640 - 654
  作者：Wagner,K. et al.

  DOI：——

  日期：——
• Structure and base catalysed cyclization of methyl (2,6-disubstituted-4-nitrophenylsulphanyl)ethanoates
  作者：Valerio Bertolasi、Kateřina Dudová、Petr Šimůnek、Jiřı́ Černý、Vladimı́r Macháček

  DOI：10.1016/s0022-2860(03)00424-1

  日期：2003.9

  The conformation of side chain -SCH2COOCH3 in title compounds in crystal agrees with the reactivity of these compounds in base catalysed ring closure in solution. In the 2,4-dinitro derivative, the side chain is oriented towards the unsubstituted ortho-position of benzene ring, in the case of the 2-methoxycarbonyl derivative towards this substituent. (C) 2003 Elsevier B.V. All rights reserved.