N-Isopentenylanthranilic acid | 1335418-55-7

• 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: N-Isopentenylanthranilic acid
• 英文别名: 2-(3-methylbut-2-enylamino)benzoic acid
• CAS: 1335418-55-7
• 化学式: C₁₂H₁₅NO₂
• 分子量: 205.257
• InChiKey: QHZUFCCMLISMJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  C₁₃H₁₇NO₂ 在 水 、 potassium hydroxide 作用下， 生成 N-Isopentenylanthranilic acid
  参考文献：
  名称：

  Nelumal A, the active principle from Ligularia nelumbifolia, is a novel farnesoid X receptor agonist

  摘要：

  A series of 29 oxyprenylated and azoprenylated phenylpropanoids were chemically synthesized and tested in transfected cultured HepG2 cells by means of the dual-luciferase assay as farnesoid X receptor (FXR) agonists, using the endogenous ligand chenodeoxycholic acid (CDCA) as reference drug. Among the tested molecules, three compounds, namely auraptene, nelumol A, and nelumal A showed a potency comparable to the endogenous ligand, with the latter natural product having a level of activity slightly superior to CDCA. Nelumal A is thus of interest as a valuable potential novel lead compound in the search for FXR agonists. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.03.057

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.