3-(2,2,6,6-tetramethylpiperidino)benzoic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 3-(2,2,6,6-tetramethylpiperidino)benzoic acid
• 英文别名: 3-(2,2,6,6-Tetramethylpiperidin-1-yl)benzoic acid
• 化学式: C₁₆H₂₃NO₂
• 分子量: 261.364
• InChiKey: DALLQUSKEHXMJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  碘甲烷 、 间溴苯甲酸 、 2,2,6,6-tetramethylpiperidinyl-lithium 以 四氢呋喃 为溶剂， 反应 1.0h， 以44%的产率得到3-溴-2-甲基苯甲酸
  参考文献：
  名称：

  ortho-Metalation of Unprotected 3-Bromo and 3-Chlorobenzoic Acids with Hindered Lithium Dialkylamides

  摘要：

  Upon treatment of 3-chloro/bromobenzoic acids with hindered lithium dialkylamides (LDA or LTMP) at -50 degreesC, lithium 3-chloroibromo-2-lithiobenzoates are generated. These dianions can be trapped as such to afford after electrophilic quenching a variety of simple 2-substituted-3-chlorolbromobenzoic acids. The 3-bromo-2-lithiobenzoate is less stable than the corresponding 3-chloro derivative and partly eliminates lithium bromide, thus setting free lithium 2,3- and 3,4-dehydrobenzoates that can be intercepted in situ with the hindered base.

  DOI：

  10.1021/jo026514t

文献信息

• <i>ortho-</i>Metalation of Unprotected 3-Bromo and 3-Chlorobenzoic Acids with Hindered Lithium Dialkylamides
  作者：Frédéric Gohier、Jacques Mortier

  DOI：10.1021/jo026514t

  日期：2003.3.1

  Upon treatment of 3-chloro/bromobenzoic acids with hindered lithium dialkylamides (LDA or LTMP) at -50 degreesC, lithium 3-chloroibromo-2-lithiobenzoates are generated. These dianions can be trapped as such to afford after electrophilic quenching a variety of simple 2-substituted-3-chlorolbromobenzoic acids. The 3-bromo-2-lithiobenzoate is less stable than the corresponding 3-chloro derivative and partly eliminates lithium bromide, thus setting free lithium 2,3- and 3,4-dehydrobenzoates that can be intercepted in situ with the hindered base.
• The First Regioselective Metalation and Functionalization of Unprotected 4-Halobenzoic Acids
  作者：Frédéric Gohier、Anne-Sophie Castanet、Jacques Mortier

  DOI：10.1021/jo0483365

  日期：2005.2.1

  By treatment with s-BuLi, s-BuLi/TMEDA, or t-BuLi at similar to-78 degreesC, 4-fluoro- and 4-chlorobenzoic acids (1a,b) are metalated preferentially in the position adjacent to the carboxylate. A complete reversal in regioselectivity is observed for 1a when treated with LTMP; a sequential process involving a rapid intraaggregate lithiation through a quasi dianion complex "QUADAC" is postulated to explain the unusual reactivity of Me2S2 and I-2.