5-(4-Methoxybenzoyl)-brenzschleimsaeuremethylester | 65650-04-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(4-Methoxybenzoyl)-brenzschleimsaeuremethylester
• 英文别名: 5-(4-methoxy-benzoyl)-furan-2-carboxylic acid methyl ester；5-Methoxycarbonyl-2-furyl 4'-methoxylphenyl ketone；5-Methoxycarbonyl-2-furyl 4'-methoxyphenyl ketone；methyl 5-(4-methoxybenzoyl)furan-2-carboxylate
• CAS: 65650-04-6
• 化学式: C₁₄H₁₂O₅
• mdl: MFCD22421290
• 分子量: 260.246
• InChiKey: QLFJXLBWTFBFNJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  65.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(4-Methoxybenzoyl)-brenzschleimsaeuremethylester 在 sodium tetrahydroborate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 1.5h， 生成 5-p-Methoxybenzyl-2-furancarbonsaeure
  参考文献：
  名称：

  Regioselective and Stereoselective Pd-Catalyzed Intramolecular Arylation of Furans: Access to Spirooxindoles and 5H-Furo[2,3-c]quinolin-4-ones

  摘要：

  Herein, we report regio- and stereoselective intramolecular direct arylations of N-(2-bromophenyl)-2-furancarboxamides 1 to produce spirooxindoles 2 and 5H-furo[2,3-c]quinolin-4-ones 3 under different reaction conditions. Specifically, in the presence of Pd(PPh3)(4) as a catalyst, PPh3 as a ligand, and K2CO3 as a base, substrates 1 underwent intramolecular alpha-arylation, possibly via a Heck insertion pathway, to provide 2, with the Zeta-isomer being favored. When the base was t-BuOLi and R-1 was an aryl group, the reaction favored Epsilon-2, possibly via an electrophilic palladation pathway. In contrast, in the presence of PdCl2 as a catalyst, (o-OMePh)(3)P as a ligand, and PivOH as an additive, substrates 1 underwent intramolecular beta-arylation to provide 3, possibly via a concerted metalation-deprotonation process.

  DOI：

  10.1021/acs.joc.6b01774
• 作为产物：
  描述：

  2-糠酸甲酯 、 对甲氧基苯甲酰氯 在 三氯化铁 作用下， 生成 5-(4-Methoxybenzoyl)-brenzschleimsaeuremethylester
  参考文献：
  名称：

  Synthesis of 1-Benzyl-3-(5‘-hydroxymethyl-2‘-furyl)indazole Analogues as Novel Antiplatelet Agents

  摘要：

  1-Benzyl-3-(5'-hydroxymethyl-2'-furyl)indazole (28, YC-1) was selected as the lead compound for systemic structural modification. After screening for antiplatelet activity, SARs of YC-1 analogues were established. Among these potent active derivatives, compounds 29, 30, 31, 44, and 45 functioned as potent activators of sGC and inhibitors of PDE5 with potency comparable to that of YC-1. In addition, compound 58 was found to be a selective and potent inhibitor of protease-activated receptor type 4 (PAR4)-dependent platelet activation.

  DOI：

  10.1021/jm010001h

文献信息

• Molecular Diversity of Tonghaosu: Synthesis of Lactam-Containing Tonghaosu Analogs
  作者：Yu-Lin Wu、Biao-Lin Yin、Zheng-Min Yang、Tai-Shan Hu

  DOI：10.1055/s-2003-41042

  日期：——

  A new type of tonghaosu analogs containing spiroketal and lactam functionality was synthesized from methyl 2-furoate and amino alcohols. The stereoselective control of spiroketal chirality was also explored.

  以 2-糠酸甲酯和氨基醇为原料，合成了一种含有螺酮和内酰胺官能团的新型 tonghaosu 类似物。此外，还探索了螺酮手性的立体选择性控制。
• Method of treating disorders related to protease-activated receptors-induced cell activation
  申请人：——

  公开号：US20020004518A1

  公开（公告）日：2002-01-10

  A method of treating a disorder related to cell activation induced by protease-activated receptors. The method includes administering to a subject in need thereof a compound having a pyrazolyl core; an aryl group, via an via an alkylene linker, bonded to 1-N of the pyrazolyl core; a second aryl group fused at 4-C and 5-C of the pyrazolyl core; and a third aryl group bonded directly to 3-C of the pyrazolyl core.

  一种治疗与蛋白酶激活受体引起的细胞活化相关障碍的方法。该方法包括向需要的受试者施用具有吡唑基核的化合物；通过烷基连接剂与吡唑基核的1-N键合的芳基团；在吡唑基核的4-C和5-C处融合的第二个芳基团；以及直接与吡唑基核的3-C键合的第三个芳基团。
• A Novel Entry to Spirofurooxindoles Involving Tandem Dearomatization of Furan Ring and Intramolecular Friedel- Crafts Reaction
  作者：Biao-Lin Yin、Jin-Qiang Lai、Ze-Ren Zhang、Huan-Feng Jiang

  DOI：10.1002/adsc.201100034

  日期：2011.8

  A copper sulfate pentahydrate-catalyzed intramolecular Friedel–Crafts reaction using an oxocarbenium species derived from a furan ring as the alkylating agent was developed for the first time. By using this protocol, spirofurooxindoles 9 with multi-reactive sites were synthesized simply and concisely. In addition, selective hydrogenation of the endo-cyclic double bond and full hydrogenation of the

  首次开发了使用五水合硫酸铜催化的分子内Friedel-Crafts反应，该反应使用衍生自呋喃环的氧碳鎓类作为烷基化剂。通过使用该协议，具有多个反应位点的螺呋喃氧吲哚9可以简单，简明地合成。此外，选择性加氢内切-环状双键和全氢化内切和外切spirofurooxindoles的-环双键9提供spirofurooxindoles 11和12，分别。
• Treatment of disorder related to low cyclic GMP levels
  申请人：——

  公开号：US20030220385A1

  公开（公告）日：2003-11-27

  Methods of treating a disorder associated with low cGMP levels. The methods include administering to a subject in need thereof an effective amount of a compound having a pyrazolyl core, a first aryl group bonded to 3-C of the pyrazolyl core, and a second aryl group fused at 4-C and 5-C of the pyrazolyl core. Also disclosed are pharmaceutical compositions containing these compounds.

  治疗与低cGMP水平相关的疾病的方法。该方法包括向需要的受试者施用具有吡唑基核、第一芳基基团与吡唑基核的3-C键合，以及第二芳基基团融合在吡唑基核的4-C和5-C处的化合物的有效量。还公开了含有这些化合物的制药组合物。
• Use of pyrazole derivatives for inhibiting thrombin-induced platelet aggregation
  申请人：Yung Shin Pharmeutical Ind. Co., Ltd.

  公开号：EP1166785A1

  公开（公告）日：2002-01-02

  A method of treating a disorder or disease related to thrombin-induced platelet aggregation. The method includes administering to a subject in need thereof a compound having a pyrazolyl core; an aryl group, via an via an alkylene linker, bonded to 1-N of the pyrazolyl core; a second aryl group fused at 4-C and 5-C of the pyrazolyl core; and a third aryl group bonded directly to 3-C of the pyrazolyl core.

  一种治疗与凝血酶诱导的血小板聚集有关的紊乱或疾病的方法。该方法包括向有需要的受试者施用一种化合物，该化合物具有吡唑基核心；通过亚烷基连接体与吡唑基核心的1-N键合的芳基；在吡唑基核心的4-C和5-C处融合的第二芳基；以及直接与吡唑基核心的3-C键合的第三芳基。