2-amino-4-bromo-3-(3-methylbut-2-enyl)benzoic acid | 1335418-67-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-amino-4-bromo-3-(3-methylbut-2-enyl)benzoic acid
• CAS: 1335418-67-1
• 化学式: C₁₂H₁₄BrNO₂
• 分子量: 284.153
• InChiKey: GWDLJTGQPCGYSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-甲基-3-丁烯-2-醇 、 2-氨基-4-溴苯甲酸 在 palladium diacetate 、 sodium 3-(diphenylphosphanyl)benzenesulfonate 作用下， 以 水 为溶剂， 反应 48.0h， 以76%的产率得到4-bromo-2-(3-methylbut-2-enylamino)benzoic acid
  参考文献：
  名称：

  Palladium-Catalyzed Mono-N-allylation of Unprotected Anthranilic Acids with Allylic Alcohols in Aqueous Media

  摘要：

  Palladium-catalyzed N-allylation of anthranilic acids 1a-j with allyl alcohol 2a in the presence of Pd(OAc)(2), sodium diphenylphosphinobenzene-3-sulfonate (TPPMS) in THF-H2O at room temperature gave only mono-N-allylated anthranilic acids 3a-j in good yields (70-98%). The reactions of 4-bromoanthranilic acid 1i with 2-methyl-3-buten-2-ol 2b showed complete chemoselectivity in N-allylation (neutral conditions) and C-vinylation (basic conditions). In our catalytic system, the keys to success are use of an unprotected anthranilic acid as a starting material and the presence of water in the reaction medium. The carboxyl group of anthranilic acid and water may play important roles for the smooth generation of the pi-allyl palladium species by activation of the hydroxyl group of the allylic alcohol.

  DOI：

  10.1021/jo201691e

文献信息

• Palladium-Catalyzed Mono-<i>N</i>-allylation of Unprotected Anthranilic Acids with Allylic Alcohols in Aqueous Media
  作者：Hidemasa Hikawa、Yuusaku Yokoyama

  DOI：10.1021/jo201691e

  日期：2011.10.21

  Palladium-catalyzed N-allylation of anthranilic acids 1a-j with allyl alcohol 2a in the presence of Pd(OAc)(2), sodium diphenylphosphinobenzene-3-sulfonate (TPPMS) in THF-H2O at room temperature gave only mono-N-allylated anthranilic acids 3a-j in good yields (70-98%). The reactions of 4-bromoanthranilic acid 1i with 2-methyl-3-buten-2-ol 2b showed complete chemoselectivity in N-allylation (neutral conditions) and C-vinylation (basic conditions). In our catalytic system, the keys to success are use of an unprotected anthranilic acid as a starting material and the presence of water in the reaction medium. The carboxyl group of anthranilic acid and water may play important roles for the smooth generation of the pi-allyl palladium species by activation of the hydroxyl group of the allylic alcohol.