3-methoxycarbonyl-5-methoxy-7-methyl-2H-1,4-benzothiazine | 17054-99-8

• 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: 3-methoxycarbonyl-5-methoxy-7-methyl-2H-1,4-benzothiazine
• 英文别名: 3-Carbomethoxy-5-methoxy-7-methyl-2H-1,4-benzothiazin；5-methoxy-7-methyl-2H-benzo[1,4]thiazine-3-carboxylic acid methyl ester；methyl 5-methoxy-7-methyl-2H-1,4-benzothiazine-3-carboxylate
• CAS: 17054-99-8
• 化学式: C₁₂H₁₃NO₃S
• 分子量: 251.306
• InChiKey: FMAAOFBKLKSYGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  73.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  S-(2,3-dihydroxy-5-methyl-phenyl)-cysteine methyl ester; hydrochloride 在 氧气 、 碳酸氢钠 作用下， 反应 0.5h， 生成 3-methoxycarbonyl-5-methoxy-7-methyl-2H-1,4-benzothiazine
  参考文献：
  名称：

  Prota,G. et al., Gazzetta Chimica Italiana, 1967, vol. 97, p. 1451 - 1478

  摘要：

  DOI：

文献信息

• Zinc-Catalyzed Oxidation of 5-<i>S</i>-Cysteinyldopa to 2,2‘-Bi(2<i>H</i>-1,4-benzothiazine):  Tracking the Biosynthetic Pathway of Trichochromes, the Characteristic Pigments of Red Hair
  作者：Alessandra Napolitano、Paola Di Donato、Giuseppe Prota

  DOI：10.1021/jo010320g

  日期：2001.10.1

  Trichochromes, the peculiar pigments of red human hair, featuring the Delta (2,2')-bi(2H-1,4-benzothiazine) skeleton, are known to arise from cysteinyldopas, mainly the 5-S-isomer (5). However, the mode of formation and the direct precursors have remained largely undefined. To fill this gap, we investigated the oxidation of 5 in air or with chemical and enzymatic agents under biomimetic conditions. In the presence of zinc ions, which occur in epidermal tissues at significant concentrations, the reaction course is diverted toward the formation of a labile 3-carboxy-2H-1,4-benzothiazine intermediate (11), which was identified by direct NMR analysis. Structural formulation was supported by characterization of the analogous compound 13 isolated from oxidation of the model 5-methyl-3-S-cysteinylcatechol (12) after methylation. In the further stages of the oxidation, diastereomeric 2,2'-bi(2H-1,4-benzothiazine) 15 and 14 were obtained from 5 and 12, respectively, the reaction proceeding at a higher rate and to a greater extent in the presence of acids. The dimers were shown to readily convert to each other in the presence of acids. In the case of the methylated dimers 14, a 2,2'-bi(4H-1,4-benzothiazine) intermediate (16) was isolated and characterized. In acidic media, trichochrome C (1a), the most abundant in red human hair, was smoothly formed from aerial oxidation of 15, and under similar conditions, trichochrome-related products (17 and 18) were obtained from 14 prior to or after methylation. The presence of la and precursors 5 and 15 was investigated by HPLC analysis of red hair samples following mild proteolytic digestion. On the basis of these data, a likely biosynthetic route to trichochrome pigments of red human hair is depicted.
• Prota,G. et al., Gazzetta Chimica Italiana, 1967, vol. 97, p. 1451 - 1478
  作者：Prota,G. et al.

  DOI：——

  日期：——