karanjic acid | 487-56-9

• 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: karanjic acid
• 英文别名: 4-hydroxy-benzofuran-5-carboxylic acid；4-Hydroxy-benzofuran-5-carbonsaeure；4-Hydroxybenzofuran-5-carboxylic acid；4-hydroxy-1-benzofuran-5-carboxylic acid
• CAS: 487-56-9
• 化学式: C₉H₆O₄
• 分子量: 178.144
• InChiKey: UCRGNGLRQIWOTB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  70.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  karanjic acid 在 sodium hydroxide 、 氯仿 作用下， 生成 4-羟基-5-苯并呋喃甲醛
  参考文献：
  名称：

  Limaye, Rasayanam, 1936, vol. 1, p. 1,14

  摘要：

  DOI：
• 作为产物：
  描述：

  苯并呋喃-4-醇 在 碳酸氢钠 作用下， 生成 karanjic acid
  参考文献：
  名称：

  Limaye, Rasayanam, 1936, vol. 1, p. 1,14

  摘要：

  DOI：

文献信息

• A tautomeric ligand enables directed C‒H hydroxylation with molecular oxygen
  作者：Zhen Li、Zhen Wang、Nikita Chekshin、Shaoqun Qian、Jennifer X. Qiao、Peter T. Cheng、Kap-Sun Yeung、William R. Ewing、Jin-Quan Yu

  DOI：10.1126/science.abg2362

  日期：2021.6.25

  challenging when oxygen is used as the oxidant. Here, we report a palladium complex bearing a bidentate pyridine/pyridone ligand that efficiently catalyzes this reaction at ring positions adjacent to carboxylic acids. Infrared, x-ray, and computational analysis support a possible role of ligand tautomerization from mono-anionic (L,X) to neutral (L,L) coordination in the catalytic cycle of aerobic carbon–hydrogen

  当使用氧气作为氧化剂时，使用过渡金属催化剂对芳基碳氢键进行羟基化已被证明具有挑战性。在这里，我们报告了一种钯配合物，它带有双齿吡啶/吡啶酮配体，可在与羧酸相邻的环位置有效地催化该反应。红外、X 射线和计算分析支持从单阴离子 (L,X) 到中性 (L,L) 配位的配体互变异构在好氧碳氢羟基化反应的催化循环中的可能作用。由杂环决定的传统位点选择性被这种催化剂推翻，从而允许在以前无法接近的位点对药物感兴趣的化合物进行后期修饰。
• Synthetic Studies on the Benzofuran Derivatives. Part I. A New Synthesis of Karanjin
  作者：Yoshiyuki Kawase、Takashi Matsumoto、Kenji Fukui

  DOI：10.1246/bcsj.28.273

  日期：1955.4

  3-methoxyflavone-7,8-furan-α-carboxylic acid (IV) was synthesised in good yield by the method of Tanaka for benzofuran synthesis and was decarboxylated in quinoline with copper powder into karanjin (I).

  以7-羟基-3-甲氧基黄酮-8-醛(II)为原料，采用田中合成苯并呋喃的方法以良好收率合成3-甲氧基黄酮-7,8-呋喃-α-羧酸(IV)并脱羧将喹啉与铜粉制成卡兰金（Ⅰ）。
• [EN] A TAUTOMERIC LIGAND ENABLES BIOMIMETIC C-H HYDROXYLATION WITH MOLECULAR OXYGEN<br/>[FR] LIGAND TAUTOMÈRE PERMETTANT UNE HYDROXYLATION C-H BIOMIMÉTIQUE AVEC DE L'OXYGÈNE MOLÉCULAIRE
  申请人：SCRIPPS RESEARCH INST

  公开号：WO2022125736A1

  公开（公告）日：2022-06-16

  Disclosed herein is a process for making a compound of formula (2) by (hetero)aromatic C-H hydroxylation of a compound of formula (1): catalyzed by palladium(II) and a bidentate ligand in the presence of O2. The process is useful for instance, in the late-stage modification of medicinally important heterocycles.

  本文公开了一种通过(杂)芳基C-H羟基化化合物的公式(1)制备公式(2)的过程：在氧气存在下，钯(II)和双齿配体催化。该过程在药物重要杂环的后期修饰中非常有用。
• Synthesis of novel benzofuran isoxazolines as protein tyrosine phosphatase 1B inhibitors
  作者：Ghufran Ahmad、Pushpesh K. Mishra、Prasoon Gupta、Prem P. Yadav、Priti Tiwari、Akhilesh K. Tamrakar、Arvind K. Srivastava、Rakesh Maurya

  DOI：10.1016/j.bmcl.2006.01.062

  日期：2006.4

  PTPases are considered to be involved in the etiology of diabetes mellitus and neural diseases, such as Alzheimer's disease and Parkinson's disease. Therefore, PTPase inhibitors should be useful tools to Study the role of PTPases in these diseases and other biological phenomena, and which can be developed into chemotherapeutic agents. In the present study, we have synthesized novel benzofuran isoxazolines 13-21 via 1,3-dipolar cycloaddition reaction using karanjin (1) and kanjone (2), isolated from Pongamia pinnata fruits. All the synthesized compounds were evaluated against PTPase enzyme. Compounds 19 and 20 displayed significant inhibitory activity with IC50 values 76 and 81 mu M, respectively. (C) 2006 Published by Elsevier Ltd.
• Seshadri; Venkateswarlu, Proceedings - Indian Academy of Sciences, Section A, 1941, # 13, p. 404,407
  作者：Seshadri、Venkateswarlu

  DOI：——

  日期：——