4-hydroxy-1-methyl-2,2-dioxo-1H-2λ⁶,1-benzothiazine-3-carboxylic acid methyl ester | 1492047-38-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 英文名称: 4-hydroxy-1-methyl-2,2-dioxo-1H-2λ⁶,1-benzothiazine-3-carboxylic acid methyl ester
• 英文别名: Methyl 4-hydroxy-1-methyl-2,2-dioxo-1h-2lambda6,1-benzothiazine-3-carboxylate；methyl 4-hydroxy-1-methyl-2,2-dioxo-2λ6,1-benzothiazine-3-carboxylate
• CAS: 1492047-38-7
• 化学式: C₁₁H₁₁NO₅S
• 分子量: 269.278
• InChiKey: MDCSPKSWURMHEJ-UHFFFAOYSA-N

物化性质

• 沸点：
  433.9±55.0 °C(Predicted)
• 密度：
  1.514±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  92.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-hydroxy-1-methyl-2,2-dioxo-1H-2λ⁶,1-benzothiazine-3-carboxylic acid methyl ester 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 0.5h， 以89%的产率得到potassium 3-methoxycarbonyl-1-methyl-2,2-dioxo-1-2λ⁶,1-benzothiazin-4-olate
  参考文献：
  名称：

  2,1-Benzothiazine 2,2-Dioxides. 9*. Alkylation of Methyl 4-Hydroxy-1-Methyl-2,2-Dioxo-1Н-2λ6,1-Benzothiazine-3-Carboxylate with Ethyl Iodide

  摘要：

  The alkylation of methyl 4-hydroxy-1-methyl-2,2-dioxo-1De-2 lambda(6),1-benzothiazine-3-carboxylate in DMSO or acetone with ethyl iodide at 25A degrees D gave a mixture of 3-ethyl- and 4-ethoxy-substituted derivatives, in complete agreement with quantum-chemical calculations. The ratio of D- and D-alkylation products changed depending on the alkali metal carbonate used as a base. The reaction practically did not proceed in anhydrous THF or water due to the low nucleophilicity of the anion.

  DOI：

  10.1007/s10593-015-1646-0
• 作为产物：
  描述：

  邻甲氨基苯甲酸甲酯 在 sodium methylate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 4-hydroxy-1-methyl-2,2-dioxo-1H-2λ⁶,1-benzothiazine-3-carboxylic acid methyl ester
  参考文献：
  名称：

  2,1-苯并噻嗪2,2-二氧化物。1. 1-R-4-羟基-2,2-二氧代-1 H-2λ6，1-苯并噻嗪-3-羧酸酯的合成，结构及止痛活性

  摘要：

  一系列1-R-4-羟基-2,2-二氧代-1-的合成制备方法的ħ -2λ 6，1-苯并噻嗪-3-羧酸盐已被开发出来。在1-N-甲基衍生物的实例上已经研究了这类化合物的空间结构的特殊特征。给出了研究所得物质的镇痛特性的结果。

  DOI：

  10.1007/s10593-013-1388-9

文献信息

• 2,1-Benzothiazine 2,2-Dioxides. 4*. Synthesis, Structure, and Analgesic Properties of 4-Hydroxy-1-Methyl-2,2-Dioxo-N-(Pyridin-2-yl)-1H-2λ6,1-Benzothiazine-3-Carboxamides
  作者：I. V. Ukrainets*、L. A. Petrushova、S. P. Dzyubenko、Liu Yangyang

  DOI：10.1007/s10593-014-1508-1

  日期：2014.7

  An improved method has been proposed for the reaction of the methyl ester of 4-hydroxy-1-methyl-2,2-di-oxo-1H-2λ6,1-benzothiazine-3-carboxylic acid with hetarylamines to give 4-hydroxy-1-methyl-2,2-di-oxo-N-(pyridin-2-yl)-1H-2λ6,1-benzothiazine-3-carboxamides and analogs with the similar structure in good yield and purity. X-ray diffraction structural analysis has indicated that these products exist

  一种改进的方法已经提出了的甲基酯的反应4-羟基-1-甲基-2,2-二氧代-1H-2λ 6，1-苯并噻嗪-3-羧酸与hetarylamines，得到4-羟基-1-甲基-2,2-二氧代-N-（吡啶-2-基）-1H-2λ 6，1-苯并噻嗪-3-甲酰胺，并用良好的产率和纯度的类似结构的类似物。X射线衍射结构分析表明这些产物以内盐形式存在。这些化合物的质谱研究表明，它们具有特征性的挤出SO 2的趋势。药理学测试已经显示出比已知的奥昔康类药物具有更好的止痛性能的有前途的化合物。
• 2,1-Benzothiazine 2,2-dioxides 10*. Reaction of alkyl 1-R-4-hydroxy-2,2-dioxo-1Н-2λ6,1-benzothiazine-3-carboxylates with 1H-1,2,4-triazol-5-amine
  作者：Igor V. Ukrainets、Lidiya A. Petrushova、Galina Sim、Natalya L. Bereznyakova

  DOI：10.1007/s10593-015-1665-x

  日期：2015.1

  The reaction of alkyl 1-R-4-hydroxy-2,2-dioxo-1Н-2λ6,1-benzothiazine-3-carboxylates with 1H-1,2,4-triazol-5-amine in refluxing xylene produced not only 1-R-4-hydroxy-2,2-dioxo-N-(1H-1,2,4-triazol-5-yl)-1H-2λ6,1-benzothiazine-3-carboxamides, but also 6,6-dioxides of 7-R-3H-[1,2,4]triazolo[5',1':2,3]pyrimido[5,4-c][2,1]benzothiazin-5(7H)-ones.

  烷基1-R-4-羟基-2,2-二氧代- 1的反应Н -2λ 6，1-苯并噻嗪-3-羧酸与1- ħ -1,2,4-三唑-5-胺在回流的二甲苯产生不仅1-R-4-羟基-2,2-二氧代- ñ - （1个ħ -1,2,4-三唑-5-基）-1 ħ -2λ 6，1-苯并噻嗪-3-羧酰胺，但也有7-R-3 H- [1,2,4]三唑[5'，1'：2,3]嘧啶[5,4- c ] [2,1]苯并噻嗪-5（6,6-dioxides）7 H）-一个。
• 2,1-Benzothiazine 2,2-Dioxides. 5*. Hydrolysis of Alkyl 1-R-4-Hydroxy-2,2-Dioxo-1Н-2λ6,1-Benzo-Thiazine-3-Carboxylates**
  作者：I. V. Ukrainets、L. A. Petrushova、S. P. Dzyubenko、Liu Yangyang

  DOI：10.1007/s10593-014-1563-7

  日期：2014.10

  Hydrolysis of 1-R-4-hydroxy-2,2-dioxo-1De-2 lambda(6),1-benzothiazine-3-carboxylate esters in HCl-AcOH-H2O mixture at 60A degrees D was accompanied by decarboxylation and led to 1-R-4-oxo-3,4-dihydro-1H-2 lambda(6),1-benzo-thiazine-2,2-diones. In the alkaline medium, regardless of the type of the substituent at position 1, analogous structural transformations occurred at first, but the thiazine ring was also destroyed along with the ester fragment when performing the reaction for a longer time.
• 2,1-Benzothiazine 2,2-Dioxides. 3*. 4-Hydroxy-1-Methyl-2,2-Dioxo-N-(1,3-Thiazol-2-yl)-1Н-2λ6,1-Benzothiazine-3-Carboxamides – a New Group of Potential Analgetics
  作者：I. V. Ukrainets、L. A. Petrushova、S. P. Dzyubenko、G. Sim

  DOI：10.1007/s10593-014-1452-0

  日期：2014.4

  We have developed an effective synthetic method and prepared several 4-hydroxy-1-methyl-2,2-dioxo-N-(1,3-thiazol-2-yl)-1De-2 lambda(6),1-benzothiazine-3-carboxamides and a few structurally related heterocyclic arylamides. The structural features of one of the substituted thiazolyl-2-amides obtained have been investigated. Compounds with a high analgesic activity have been identified within this group by pharmacological screening.