3-carboxymethyl-2-methylbenzoxazol-3-ium bromide | 144189-77-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-carboxymethyl-2-methylbenzoxazol-3-ium bromide
• 英文别名: 3-(Carboxymethyl)-2-methyl-1,3-benzoxazol-3-ium bromide；2-(2-methyl-1,3-benzoxazol-3-ium-3-yl)acetic acid;bromide
• CAS: 144189-77-5
• 化学式: Br*C₁₀H₁₀NO₃
• 分子量: 272.098
• InChiKey: IMARPUCJBKHMNW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.88
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  54.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-carboxymethyl-2-methylbenzoxazol-3-ium bromide 以 氘代二甲亚砜 为溶剂， 反应 4.0h， 生成 (2-hydroxy-2-methylbenzoxazol-3-yl)acetic acid
  参考文献：
  名称：

  NMR spectroscopy study of 2-methylbenzoxazolium salts hydroxylation in DMSO-d6 solution

  摘要：

  2-Methylbenzoxazolium salts showed an unexpected transformation at room temperature, promoted by residual water present in dimethyl sulfoxide. This transformation was followed up inside of an NMR sample tube using DMSO-d(6) as solvent, in a series of representative quaternary ammonium salts with carboxymethyl, ethyl, pentyl and decyl N-alkyl chains, resulting in an exclusive product. The corresponding benzothiazolium and benzoselenazolium salts presented a si similar behavior after heating at a temperature of 50 degrees C with the addition of one drop of D2O for the first of these two salts. This reaction could play a very important role in explaining certain secondary reactions occurring in the preparation of compounds where these salts are precursors, classically in cyanine dye synthesis. Four new benzoxazolols were characterized by NMR spectroscopy and HR FAB-MS. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.07.091
• 作为产物：
  描述：

  2-甲基苯并唑 、 溴乙酸乙酯 在 四丁基碘化铵 、 氢溴酸 作用下， 以 甲苯 为溶剂， 反应 1.0h， 生成 3-carboxymethyl-2-methylbenzoxazol-3-ium bromide
  参考文献：
  名称：

  Westphal Reaction in Solid-Phase

  摘要：

  [GRAPHIC]A library of cycloimonium salts has been prepared through Westphal reaction in solid-phase. By reaction of solid-support-bound azolium or azinium acetates 2, 1,2-diketones 4, and base, cycloimonium salts 5 were synthesized in good to high yield and purities.

  DOI：

  10.1021/ol035417z

文献信息

• Westphal Reaction in Solid-Phase
  作者：Francisca Delgado、M. Lourdes Linares、Ramón Alajarín、Juan J. Vaquero、Julio Alvarez-Builla

  DOI：10.1021/ol035417z

  日期：2003.10.1

  [GRAPHIC]A library of cycloimonium salts has been prepared through Westphal reaction in solid-phase. By reaction of solid-support-bound azolium or azinium acetates 2, 1,2-diketones 4, and base, cycloimonium salts 5 were synthesized in good to high yield and purities.
• NMR spectroscopy study of 2-methylbenzoxazolium salts hydroxylation in DMSO-d6 solution
  作者：Ricardo Santos、Luís M. Fernandes、Renato F. Boto、Rogério Simões、Paulo Almeida

  DOI：10.1016/j.tetlet.2006.07.091

  日期：2006.9

  2-Methylbenzoxazolium salts showed an unexpected transformation at room temperature, promoted by residual water present in dimethyl sulfoxide. This transformation was followed up inside of an NMR sample tube using DMSO-d(6) as solvent, in a series of representative quaternary ammonium salts with carboxymethyl, ethyl, pentyl and decyl N-alkyl chains, resulting in an exclusive product. The corresponding benzothiazolium and benzoselenazolium salts presented a si similar behavior after heating at a temperature of 50 degrees C with the addition of one drop of D2O for the first of these two salts. This reaction could play a very important role in explaining certain secondary reactions occurring in the preparation of compounds where these salts are precursors, classically in cyanine dye synthesis. Four new benzoxazolols were characterized by NMR spectroscopy and HR FAB-MS. (c) 2006 Elsevier Ltd. All rights reserved.