3-(diallylamino)benzoic acid

• 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: 3-(diallylamino)benzoic acid
• 英文别名: 3-diallylamino-benzoic acid；3-Diallylamino-benzoesaeure；3-[Bis(prop-2-enyl)amino]benzoic acid
• 化学式: C₁₃H₁₅NO₂
• 分子量: 217.268
• InChiKey: ISKIXWDGNMWTLR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.15
• 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：

  间氨基苯甲酸 、 烯丙醇 在 palladium diacetate 、 sodium 3-(diphenylphosphanyl)benzenesulfonate 作用下， 以 四氢呋喃 、 水 为溶剂， 以62%的产率得到3-(diallylamino)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

• Aminobenzoic Acid Derivatives
  申请人：Ivancic Danielle N.

  公开号：US20130281336A1

  公开（公告）日：2013-10-24

  This invention relates to N-alkylated anthranilic acid derivative and their use in lubricants, such as engine oils, as TBN boosters. The invention particularly relates to compositions that deliver an ash-free base to a lubricant in the form of a basic amine additive, without adversely impacting seal compatibility and/or degradation, and methods thereof.

  本发明涉及N-烷基化蒽酸衍生物及其在润滑剂中的应用，例如在发动机油中作为TBN增强剂。本发明特别涉及以基础胺添加剂的形式向润滑剂提供无灰基础的组合物，而不会对密封兼容性和/或降解产生不利影响，以及相关方法。
• Aminobenzoic acid derivatives
  申请人：The Lubrizol Corporation

  公开号：US10059900B2

  公开（公告）日：2018-08-28

  This invention relates to N-alkylated anthranilic acid derivative and their use in lubricants, such as engine oils, as TBN boosters. The invention particularly relates to compositions that deliver an ash-free base to a lubricant in the form of a basic amine additive, without adversely impacting seal compatibility and/or degradation, and methods thereof.

  本发明涉及 N-烷基蒽酸衍生物及其在润滑油（如发动机油）中作为 TBN 增效剂的用途。本发明尤其涉及能以碱性胺添加剂的形式向润滑油提供无灰碱而不会对密封件兼容性和/或降解产生不利影响的组合物及其方法。
• Griess, Chemische Berichte, 1872, vol. 5, p. 1038,1041
  作者：Griess

  DOI：——

  日期：——
• AMINOBENZOIC ACID DERIVATIVES
  申请人：The Lubrizol Corporation

  公开号：EP2619293A1

  公开（公告）日：2013-07-31
• Lubricating Composition With Improved TBN Retention
  申请人：Galic Raguz Mary

  公开号：US20140187458A1

  公开（公告）日：2014-07-03

  The invention provides a lubricating composition containing a diarylamine, an aminobenzene and an oil of lubricating viscosity. The invention further relates to the use of the lubricating composition in an internal combustion engine. The invention further relates to the use of the lubricating composition to improve TBN retention.