2-(cinnamylamino)benzoic acid | 99753-82-9

• 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-(cinnamylamino)benzoic acid
• 英文别名: 2-[[(E)-3-phenylprop-2-enyl]amino]benzoic acid
• CAS: 99753-82-9
• 化学式: C₁₆H₁₅NO₂
• 分子量: 253.301
• InChiKey: VYSKLRHHFYJESB-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  肉桂醇 、 邻氨基苯甲酸 在 palladium diacetate 、 sodium 3-(diphenylphosphanyl)benzenesulfonate 作用下， 以 水 为溶剂， 以100%的产率得到2-(cinnamylamino)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

• Encapsulation of bulky fragrance molecules
  申请人：Takasago International Corporation

  公开号：EP1894603B1

  公开（公告）日：2014-11-19
• Non-aldehyde cinnamon flavor and delivery systems therefor
  申请人：Cadbury Adams USA LLC

  公开号：EP1967080B1

  公开（公告）日：2010-06-02
• MANUFACTURING METHOD OF 2-HYDROXY-5-PHENYLALKYLAMINOBENZOIC ACID DERIVATIVES AND THEIR SALTS
  申请人：Neurotech Pharmaceuticals Co., Ltd.

  公开号：EP2215050A2

  公开（公告）日：2010-08-11
• US4185115A
  申请人：——

  公开号：US4185115A

  公开（公告）日：1980-01-22
• [EN] MANUFACTURING METHOD OF 2-HYDROXY-5-PHENYLALKYLAMINOBENZOIC ACID DERIVATIVES AND THEIR SALTS<br/>[FR] PROCÉDÉ DE PRODUCTION DE DÉRIVÉS D'ACIDE 2-HYDROXY-5-PHÉNYLALKYLAMINOBENZOÏQUE ET LEUR SELS
  申请人：NEUROTECH CO LTD

  公开号：WO2009064084A2

  公开（公告）日：2009-05-22

  The present invention provides an efficient method for mass-producing 2-hydroxy-5- ( substituted)phenylalkylaminobenzoic acid derivative represented by the specific Chemical formula or its salt, particularly 2-hydroxy-5-[ 2-( 4- trif luoromethylphenyl)ethylamino] benzoic acid or its salt.