2,2,2-Trichloroethyl 3-Acetyl-2,6-dimethoxybenzoate | 148460-82-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2,2-Trichloroethyl 3-Acetyl-2,6-dimethoxybenzoate
• CAS: 148460-82-6
• 化学式: C₁₃H₁₃Cl₃O₅
• 分子量: 355.602
• InChiKey: IWMGGALXDLKLPY-UHFFFAOYSA-N

物化性质

• 沸点：
  495.8±45.0 °C(Predicted)
• 密度：
  1.380±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.43
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2,2,2-Trichloroethyl 3-Acetyl-2,6-dimethoxybenzoate 在 盐酸 、 对甲苯磺酸 、 间氯过氧苯甲酸 作用下， 以 氯仿 、 丙酮 、 三氟乙酸 为溶剂， 反应 46.0h， 生成 2,2,2-Trichloroethyl 2,6-Dimethoxy-3-pivaloylbenzoate
  参考文献：
  名称：

  Pivaloyl-directed regioselective syntheses of 2,3,6-trioxygenated benzamides: phenolic metabolites of remoxipride

  摘要：

  The regioselective syntheses of (S)-5-bromo-2,6-dimethoxy-N-[(1-ethyl-2-pyrrolidinyl)methyl]-3-hydroxybenzamide (2) and (S)-5-bromo-N-[(1-ethyl-2-pyrrolidinyl)methyl]-3-hydroxy-6-methoxy-salicylamide (3) from 2,6-dimethoxybenzoic acid and 4-methoxycatechol are described. The latter compound was protected and ortho-lithiated to introduce the carboxyl function in a regioselective manner. Regiocontrol in bromination and demethylation was achieved by introduction of a bulky pivaloyl group. This strategy also enabled the use of a common intermediate as an alternative synthesis of the catechol 3.

  DOI：

  10.1021/jo00065a015
• 作为产物：
  描述：

  2,6-二甲氧基苯甲酸 在 氯化亚砜 、 N,N-二甲基甲酰胺 、 三氟乙酸酐 作用下， 反应 24.0h， 生成 2,2,2-Trichloroethyl 3-Acetyl-2,6-dimethoxybenzoate
  参考文献：
  名称：

  Pivaloyl-directed regioselective syntheses of 2,3,6-trioxygenated benzamides: phenolic metabolites of remoxipride

  摘要：

  The regioselective syntheses of (S)-5-bromo-2,6-dimethoxy-N-[(1-ethyl-2-pyrrolidinyl)methyl]-3-hydroxybenzamide (2) and (S)-5-bromo-N-[(1-ethyl-2-pyrrolidinyl)methyl]-3-hydroxy-6-methoxy-salicylamide (3) from 2,6-dimethoxybenzoic acid and 4-methoxycatechol are described. The latter compound was protected and ortho-lithiated to introduce the carboxyl function in a regioselective manner. Regiocontrol in bromination and demethylation was achieved by introduction of a bulky pivaloyl group. This strategy also enabled the use of a common intermediate as an alternative synthesis of the catechol 3.

  DOI：

  10.1021/jo00065a015