rac-tert-butyl 2-(hydroxybenzyl)thiazole-4-carboxylate | 1380359-06-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: rac-tert-butyl 2-(hydroxybenzyl)thiazole-4-carboxylate
• CAS: 1380359-06-7
• 化学式: C₁₅H₁₇NO₃S
• 分子量: 291.371
• InChiKey: ASSYDFAHYGDIMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.18
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  59.42
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  rac-tert-butyl 2-(hydroxybenzyl)thiazole-4-carboxylate 、 乙酰氯 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以90%的产率得到rac-tert-butyl 2-(acetoxy(phenyl)methyl)thiazole-4-carboxylate
  参考文献：
  名称：

  Chemoenzymatic synthesis of highly enantiomerically enriched secondary alcohols with a thiazolic core

  摘要：

  Stereoselective preparative enzymatic acylation and hydrolysis/methanolysis of various C-substituted rac-thiazol-2-yl-methanols were achieved for the preparation of enantiopure or enantiomerically enriched, naturally occurring 2-hydroxymethylthiazoles. The absolute configurations of the resulting secondary alcohols were determined by a detailed H-1 NMR study of Mosher's derivatives. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.03.014
• 作为产物：
  描述：

  2-溴噻唑-4-甲酸叔丁酯 、 苯甲醛 在 lithium chloro-isopropyl-magnesium chloride 、 水 、 氯化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.92h， 以74%的产率得到rac-tert-butyl 2-(hydroxybenzyl)thiazole-4-carboxylate
  参考文献：
  名称：

  Chemoenzymatic synthesis of highly enantiomerically enriched secondary alcohols with a thiazolic core

  摘要：

  Stereoselective preparative enzymatic acylation and hydrolysis/methanolysis of various C-substituted rac-thiazol-2-yl-methanols were achieved for the preparation of enantiopure or enantiomerically enriched, naturally occurring 2-hydroxymethylthiazoles. The absolute configurations of the resulting secondary alcohols were determined by a detailed H-1 NMR study of Mosher's derivatives. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.03.014