coumalic acid benzyl ester | 61752-10-1

• 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: coumalic acid benzyl ester
• 英文别名: 6-oxo-6H-pyran-3-carboxylic acid benzyl ester；6-Oxo-6H-pyran-3-carbonsaeure-benzylester；Cumalinsaeurebenzylester；Benzyl 6-oxopyran-3-carboxylate
• CAS: 61752-10-1
• 化学式: C₁₃H₁₀O₄
• 分子量: 230.22
• InChiKey: VMJBTCOZXQSHLC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  coumalic acid benzyl ester 在 劳森试剂 作用下， 以 苯 为溶剂， 以41 %的产率得到C₁₃H₁₀O₂S₂
  参考文献：
  名称：

  Controllable Cycloadditions between 2H-(Thio)pyran-2-(thi)ones and Strained Alkynes: A Click-and-Release Strategy for COS/H₂S Generation

  摘要：

  DOI：

  10.1021/acs.orglett.2c02819
• 作为产物：
  描述：

  香豆酸 、 苯甲醇 在 APTS 作用下， 反应 15.0h， 生成 coumalic acid benzyl ester
  参考文献：
  名称：

  Acaricidal Activity of Tonka Bean Extracts. Synthesis and Structure−Activity Relationships of Bioactive Derivatives

  摘要：

  The acaricidal effects of tonka bean, Dipterix odorata, extracts were investigated on Dermatophagoides pteronyssinus, the European house dust mite, and compared with benzyl benzoate as a standard acaricidal compound. A cyclohexane extract was the most effective, with an EC50 = 0.075 g/m(2) after a 24 h period, as compared with benzyl benzoate (0.025 g/m(2)). Bioassay-guided fractionation of this extract led to the isolation of coumarin (1). Pharmacomodulation of this compound led us to test 20 analogues (2-21), which were either synthesized or purchased.

  DOI：

  10.1021/np020563j

文献信息

• Enantioselective Synthesis of Chiral Medium-Sized Cyclic Compounds via Tandem Cycloaddition/Cope Rearrangement Strategy
  作者：Xing Gao、Miaoren Xia、Chunhao Yuan、Leijie Zhou、Wei Sun、Cheng Li、Bo Wu、Dongyu Zhu、Cheng Zhang、Bing Zheng、Dongqi Wang、Hongchao Guo

  DOI：10.1021/acscatal.8b04590

  日期：2019.3.1

  tandem [3 + 2] cycloaddition/Cope rearrangement reaction of vinylethylene carbonates (VECs) with coumalates or pyrones. Under mild conditions, palladium-catalyzed asymmetric tandem reaction of various substituted VECs and coumalates or pyrones proceeds smoothly to produce the corresponding medium-sized heterocyclic compounds in high yields with very high enantioselectivities. Moreover, the reaction on the

  九元含环双环[5.2.2]四氢氧代己酮骨架是通过碳酸乙烯亚乙酯（VECs）与香豆酸酯或吡喃酮的串联[3 + 2]环加成/ Cope重排反应而对映选择性地构建的。在温和的条件下，各种取代的VEC和香豆酸盐或吡喃酮的钯催化不对称串联反应可顺利进行，从而以高收率和很高的对映选择性生产相应的中型杂环化合物。而且，在克规模的反应和产物的进一步多样化转化是可行的。通过控制实验和DFT计算研究了反应机理，结果表明反应是通过串联[3 + 2]环加成/ Cope重排途径进行的，而不是通过[5 + 4]环加成途径进行的。
• Iridium-catalyzed enantioselective olefinic C(sp²)–H allylic alkylation
  作者：Rahul Sarkar、Santanu Mukherjee

  DOI：10.1039/d0sc06208a

  日期：——

  The first iridium-catalyzed enantioselective olefinic C(sp2)–H allylic alkylation is developed in cooperation with Lewis base catalysis. This reaction, catalyzed by cinchonidine and an in situ generated cyclometalated Ir(I)/phosphoramidite complex, makes use of the latent enolate character of an α,β-unsaturated carbonyl compound, namely coumalate ester, to introduce an allyl group at its α-position

  第一个铱催化的对映选择性烯属 C(sp 2 )–H 烯丙基烷基化是与路易斯碱催化合作开发的。该反应由辛可尼定和原位生成的环金属化 Ir()/亚磷酰胺络合物催化，利用 α,β-不饱和羰基化合物（即香豆酸酯）的潜在烯醇化特性，在其 α 位引入烯丙基以支链选择性方式，产率中等至良好，具有良好至优异的对映选择性（高达 98 : 2 er）。
• TRPM8 ANTAGONISTS AND THEIR USE IN TREATMENTS
  申请人：Biswas Kaustav

  公开号：US20130157996A1

  公开（公告）日：2013-06-20

  Compounds of Formula I are useful as antagonists of TRPM8. Such compounds are useful in treating a number of TRPM8 mediated disorders and conditions and may be used to prepare medicaments and pharmaceutical compositions useful for treating such disorders and conditions. Examples of such disorders include, but are not limited to, migraines and neuropathic pain. Compounds of Formula I have the following structure: where the definitions of the variables are provided herein.

  公式I的化合物可用作TRPM8的拮抗剂。这些化合物在治疗许多TRPM8介导的疾病和病症方面非常有用，并可用于制备用于治疗此类疾病和病症的药物和制剂。此类疾病的示例包括但不限于偏头痛和神经病性疼痛。公式I的化合物具有以下结构：其中变量的定义在此提供。
• TRPM8 antagonists and their use in treatments
  申请人：Chen Jian J.

  公开号：US08710043B2

  公开（公告）日：2014-04-29

  Compounds of Formula I are useful as antagonists of TRPM8. Such compounds are useful in treating a number of TRPM8 mediated disorders and conditions and may be used to prepare medicaments and pharmaceutical compositions useful for treating such disorders and conditions. Examples of such disorders include, but are not limited to, migraines and neuropathic pain. Compounds of Formula I have the following structure: where the definitions of the variables are provided herein.

  式I的化合物可作为TRPM8拮抗剂使用。这些化合物可用于治疗多种TRPM8介导的疾病和症状，并可用于制备治疗此类疾病和症状的药物和制剂。这些疾病的例子包括但不限于偏头痛和神经病性疼痛。式I的化合物具有以下结构：其中变量的定义在此提供。
• Synthesis of (E)‐Enaminoesters by a 1,6‐Addition/Fragmentation Cascade Involving Coumalic Acid Esters and Secondary Amines
  作者：Tania Xavier、Sylvie Condon、Christophe Pichon、Erwan Le Gall、Marc Presset

  DOI：10.1002/ejoc.202400435

  日期：2024.8.19

  Biomass-based coumalates were found to be renewable surrogates for fossil-fuel-based propiolates for the stereoselective synthesis of (E)-enaminoesters. Insight into the reaction mechanism is provided. The process is thought to involve an original uncatalyzed 1,6-addition/fragmentation cascade involving secondary amines.

  人们发现基于生物质的香豆酸盐是基于化石燃料的丙炔酸盐的可再生替代品，用于立体选择性合成(E)-烯胺酯。提供了对反应机制的深入了解。该过程被认为涉及涉及仲胺的原始未催化 1,6-加成/断裂级联。