5-methoxycoumarin-3-carboxylic acid | 81017-29-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 5-methoxycoumarin-3-carboxylic acid
• 英文别名: 5-methoxy-3-coumarincarboxylic acid；5-methoxy-2-oxo-2H-chromen-3-carboxylic acid；5-methoxy-2-oxo-2H-1-benzopyran-3-carboxylic acid；5-methoxy-2-oxochromene-3-carboxylic acid
• CAS: 81017-29-0
• 化学式: C₁₁H₈O₅
• 分子量: 220.182
• InChiKey: WWMUWCJDRURRHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-methoxycoumarin-3-carboxylic acid 在 sodium hydrogensulfite 、 硫酸 作用下， 以 水 为溶剂， 反应 1.0h， 生成 5-甲氧基香豆素
  参考文献：
  名称：

  Synthesis and SAR studies of mono O-prenylated coumarins as potent 15-lipoxygenase inhibitors

  摘要：

  All of the mono isopentenyloxy, -geranyloxy and -farnesyloxy derivatives of coumarin were synthesized and their inhibitory potency against soybean 15-lipoxygenase (SLO) and human 15-lipoxygenase-1 (HLO-1) were determined. Amongst the synthetic analogs, 5-farnesyloxycoumarin showed the most potent inhibitory activity against SLO (IC50 = 0.8 mu M) while 6-farnesyloxycoumarin was the strongest HLO-1 inhibitor (IC50 = 1.3 mu M). The IC50 variations of the farnesyl derivatives for HLO-1 (1.3 to similar to 75 mu M) were much higher than that observed for SLO (0.8-5.8 mu M). SAR studies showed that hydrogen bonding, CH/pi, anion-pi and S-O=C interactions with Fe-III-OH, Leu408, Glu357 and Met419 were the distinct intermolecular interactions which can lead to important role of the coumarin substitution site in HLO-1 inhibitory potency, respectively. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.09.006
• 作为产物：
  描述：

  2,6-二甲氧基苯甲醛 在 硫酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 5-methoxycoumarin-3-carboxylic acid
  参考文献：
  名称：

  Armstrong, Veronica; Soto, Oriana; Valderrama, Jaime A., Synthetic Communications, 1988, vol. 18, # 7, p. 717 - 726

  摘要：

  DOI：

文献信息

• Palladium-Catalyzed Decarboxylative Cross-Coupling Reactions: A Route for Regioselective Functionalization of Coumarins
  作者：Farnaz Jafarpour、Samaneh Zarei、Mina Barzegar Amiri Olia、Nafiseh Jalalimanesh、Soraya Rahiminejadan

  DOI：10.1021/jo302778d

  日期：2013.4.5

  A straightforward, regioselective, and step-economical ligand-free palladium-catalyzed decarboxylative functionalization of coumarin-3-carboxylic acids is devised. This protocol is compatible with a wide variety of electron-donating and -withdrawing substituents and allows for construction of various biologically important π-electron extended coumarins.

  设计了一种直接的，区域选择性的，经济的，无配体的，香豆素-3-羧酸无钯催化的脱羧功能化方法。该方案与各种各样的供电子和撤电子取代基兼容，并允许构建各种生物学上重要的π电子扩展香豆素。
• Rapid Synthesis of Novel and Known Coumarin-3-carboxylic Acids Using Stannous Chloride Dihydrate under Solvent-Free Conditions
  作者：Bahador Karami、Mahnaz Farahi、Saeed Khodabakhshi

  DOI：10.1002/hlca.201100342

  日期：2012.3

  Various coumarin‐3‐carboxylic acid (=2‐oxo‐2H‐1‐benzopyran‐3‐carboxylic acid; CcaH) derivatives have been synthesized in good yields using catalytic amounts of SnCl2⋅2 H2O under solvent‐free conditions. This inexpensive, nontoxic, and readily available catalytic system (10 mol‐%) efficiently catalyzes the Knoevenagel condensation and intramolecular cyclization of various 2‐hydroxybenzaldehydes or acetophenones

  各种香豆素-3-羧酸（= 2-氧代-2- ħ -1-苯并吡喃-3-羧酸; CcaH）衍生物已在使用的SnCl催化量的良好的产率合成了2 ⋅2ħ 2 o在无溶剂条件下。这种廉价，无毒且易于获得的催化体系（10 mol％）可有效地催化Knoevenagel缩合反应以及用Meldrum酸催化各种2-羟基苯甲醛或苯乙酮的分子内环化反应。高产品收率，使用廉价且安全的催化剂以及无溶剂条件显示了经济和环境优势。
• Synthesis of 7-(furan-2-yl)-7,8,10,10a-tetrahydro-6H-benzo[c]-chromen-6,9(6aH)-diones
  作者：E. E. Shults、S. P. Bondarenko、M. M. Shakirov、I. Yu. Bagryanskaya、G. A. Tolstikov

  DOI：10.1134/s1070428010110187

  日期：2010.11

  Methods of synthesis were developed for 7-(furan-2-yl)-substituted 7,8,10,10a-tetrahydrobenzo[c] chromen-6,9-diones by regioselective [4+2]-cycloaddition of coumarin-3-carboxylic acids to 2-(3-trimethylsiloxybuta- 1,3-dien-1-yl)furans. The [4+2]-cycloaddition was efficiently catalyzed with L-proline.

  通过对香豆素-3-的区域选择性[4 + 2] -环加成反应，开发了7-（呋喃-2-基）取代的7,8,10,10a-四氢苯并[ c ] chromen -6,9-二酮的合成方法。羧酸生成2-（3-三甲基甲硅烷氧基丁-1,3-二烯-1-基）呋喃。L-脯氨酸有效地催化了[4 + 2]-环加成反应。
• NHC-Catalyzed Chemo- and Enantioselective Reaction between Aldehydes and Enals for Access to Axially Chiral Arylaldehydes
  作者：Zhiguo Zheng、Qian Liu、Xiaolin Peng、Zhichao Jin、Jian Wu

  DOI：10.1021/acs.orglett.3c04189

  日期：2024.2.2

  A chiral carbene-catalyzed chemo- and enantioselective reaction with racemic biaryl aldehydes and α-bromoenals is developed for access to axially chiral 2-arylbenzaldehydes through atroposelective dynamic kinetic resolution (DKR) processes. This atroposelective DKR strategy can tolerate a broad scope of substrates with diverse functionalities. The axially chiral 2-aryl benzaldehyde products generally

  开发了一种手性卡宾催化的与外消旋联芳醛和 α-溴烯醛的化学和对映选择性反应，用于通过对映选择性动态动力学拆分 (DKR) 过程获得轴向手性 2-芳基苯甲醛。这种肌细胞选择性 DKR 策略可以耐受具有不同功能的广泛底物。轴向手性2-芳基苯甲醛产物通常具有中等至良好的产率和对映选择性。当前方法提供的轴向手性分子可通过简单的变换而变化，以提供具有优异光学纯度的轴向手性功能分子。
• Synthesis of Coumarin-3-O-acylisoureas by Different Carbodiimides
  作者：Leonardo Bonsignore、Filippo Cottiglia、Silvio M. Lavagna、Giuseppe Loy、Daniela Secci

  DOI：10.3987/com-98-s(h)18

  日期：——

  The synthesis and isolation of some O-acylisourea derivatives are described. The reaction between coumarin-3-carboxylic acids and diisopropyl- and di-tert-butyl-carbodiimides leads only to coumarin-isourea derivatives except for two reactions which lead, as by-products, also to coumarin-urea derivatives.