2,2,2-Trichloroethyl 5-Bromo-2,6-dimethoxy-3-pivaloylbenzoate | 148460-86-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮
• 英文名称: 2,2,2-Trichloroethyl 5-Bromo-2,6-dimethoxy-3-pivaloylbenzoate
• 英文别名: 2,2,2-trichloroethyl 3-bromo-5-(2,2-dimethylpropanoyloxy)-2,6-dimethoxybenzoate
• CAS: 148460-86-0
• 化学式: C₁₆H₁₈BrCl₃O₆
• 分子量: 492.578
• InChiKey: KSYSWKXJVXTTHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.94
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2,2,2-Trichloroethyl 5-Bromo-2,6-dimethoxy-3-pivaloylbenzoate 在 氯化亚砜 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 锌 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 5.0h， 生成
  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：

  2,2,2-Trichloroethyl 3-Acetoxy-2,6-dimethoxybenzoate 在 盐酸 、 溴 作用下， 以 氯仿 、 丙酮 、 三氟乙酸 为溶剂， 反应 26.5h， 生成 2,2,2-Trichloroethyl 5-Bromo-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