7-(2-氨基-3-羟基-3-氧代丙基)-5-羟基-3,4-二氢-2H-1,4-苯并噻嗪-3-羧酸 | 30612-54-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 中文名称: 7-(2-氨基-3-羟基-3-氧代丙基)-5-羟基-3,4-二氢-2H-1,4-苯并噻嗪-3-羧酸
• 英文名称: 7-(2-amino-2-carboxy-ethyl)-5-hydroxy-3,4-dihydro-2H-benzo[1,4]thiazine-3-carboxylic acid
• 英文别名: 2H-1,4-Benzothiazine-7-propanoic acid, alpha-amino-3-carboxy-3,4-dihydro-5-hydroxy-；7-(2-amino-2-carboxyethyl)-5-hydroxy-3,4-dihydro-2H-1,4-benzothiazine-3-carboxylic acid
• CAS: 30612-54-5
• 化学式: C₁₂H₁₄N₂O₅S
• 分子量: 298.32
• InChiKey: ACUWXAUSGNGBKQ-UHFFFAOYSA-N

物化性质

• 沸点：
  617.2±55.0 °C(Predicted)
• 密度：
  1.566±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  158
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  7-(2-氨基-3-羟基-3-氧代丙基)-5-羟基-3,4-二氢-2H-1,4-苯并噻嗪-3-羧酸 以 甲醇 为溶剂， 以60%的产率得到2-Amino-3-(4-hydroxy-2-methyl-benzothiazol-6-yl)-propionic acid
  参考文献：
  名称：

  二氢-1,4-苯并噻嗪的光化学环收缩

  摘要：

  苯丙氨酸前体1a和相关的二氢-1,4-苯并噻嗪1b-f在用耐热玻璃过滤的紫外线照射下会发生环收缩，从而以高收率得到2-甲基苯并噻唑2a-f。

  DOI：

  10.1016/s0040-4039(00)76909-7
• 作为产物：
  描述：

  5-S-cysteinyldopa 在 sodium tetrahydroborate 、 双氧水 、 peroxidase 作用下， 以31%的产率得到7-(2-氨基-3-羟基-3-氧代丙基)-5-羟基-3,4-二氢-2H-1,4-苯并噻嗪-3-羧酸
  参考文献：
  名称：

  Characterisation of 1,4-benzothiazine intermediates in the oxidative conversion of 5-S-cysteinyldopa to pheomelanins

  摘要：

  Under biologically relevant conditions, oxidation of 5-S-cysteinyldopa (1) to pheomelanins proceeds through the formation of the 1,4-benothiazine 7 along with the 3-carboxy analogue 6 in much smaller amounts, as evidenced by isolation of the reduced forms 5 and 4 and by deuterium labelling experiments.

  DOI：

  10.1016/s0040-4039(00)73434-4

文献信息

• Costantini Claudio, Testa Gennaro, Crescenzi Orlando, dIschia Marco, Tetrahedron Lett, 35 (1994) N 20, S 3365-3366
  作者：Costantini Claudio, Testa Gennaro, Crescenzi Orlando, dIschia Marco

  DOI：——

  日期：——
• A new benzothiazole derivative by degradation of pheomelanins with alkaline hydrogen peroxide
  作者：Alessandra Napolitano、M. Rosaria Vincensi、Marco d'Ischia、Giuseppe Prota

  DOI：10.1016/s0040-4039(96)01483-9

  日期：1996.9

  Oxidation of natural and synthetic pheomelanins with alkaline H2O2 at room temperature led to the formation of a major product (up to 25% yield w/w) which was identified as the novel 2-carboxy-4-hydroxy-6-(2-amino-2-carboxyethyl)benzothiazole (6). Copyright (C) 1996 Published by Elsevier Science Ltd
• Photochemical ring contraction of dihydro-1,4-benzothiazines
  作者：Claudio Costantini、Gennaro Testa、Orlando Crescenzi、Marco d'Ischia

  DOI：10.1016/s0040-4039(00)76909-7

  日期：1994.5

  The pheomelanin precursor 1a and the related dihydro-1,4-benzothiazines 1b–f undergo ring contraction upon irradiation with pyrex-filtered UV light to give 2-methylbenzothiazoles 2a–f in good yields.

  苯丙氨酸前体1a和相关的二氢-1,4-苯并噻嗪1b-f在用耐热玻璃过滤的紫外线照射下会发生环收缩，从而以高收率得到2-甲基苯并噻唑2a-f。
• Characterisation of 1,4-benzothiazine intermediates in the oxidative conversion of 5-S-cysteinyldopa to pheomelanins
  作者：Alessandra Napolitano、Claudio Costantini、Orlando Crescenzi、Giuseppe Prota

  DOI：10.1016/s0040-4039(00)73434-4

  日期：1994.8

  Under biologically relevant conditions, oxidation of 5-S-cysteinyldopa (1) to pheomelanins proceeds through the formation of the 1,4-benothiazine 7 along with the 3-carboxy analogue 6 in much smaller amounts, as evidenced by isolation of the reduced forms 5 and 4 and by deuterium labelling experiments.