methyl 3-(2-oxo-2H-chromen-3-yl)propanoate | 920525-50-4

• 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: methyl 3-(2-oxo-2H-chromen-3-yl)propanoate
• 英文别名: Methyl 3-(2-oxo-2H-1-benzopyran-3-yl)propanoate；methyl 3-(2-oxochromen-3-yl)propanoate
• CAS: 920525-50-4
• 化学式: C₁₃H₁₂O₄
• 分子量: 232.236
• InChiKey: BVSPRKZMMRGVKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 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：

  methyl 3-(2-oxo-2H-chromen-3-yl)propanoate 在 potassium hydroxylamine 作用下， 以 甲醇 为溶剂， 生成 N-hydroxy-3-(2-oxo-2H-chromene-3-yl)-propionamide
  参考文献：
  名称：

  Chromen-based TNF-α converting enzyme (TACE) inhibitors: Design, synthesis, and biological evaluation

  摘要：

  A series of coumarin types MMP inhibitors were designed based on gelastatin hydroxamates (1) and evaluated for TACE, cellular TNF-alpha, and NO inhibitory activities. Among them, compounds 9b had potent inhibitory activities in enzymatic and cellular assays and good selectivity to MMP-2 and MMP-9. Further investigation of 9b will be carried out for its efficacy in RA animal model system. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.09.014
• 作为产物：
  描述：

  2-formylphenyl methyl glutarate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以37%的产率得到methyl 3-(2-oxo-2H-chromen-3-yl)propanoate
  参考文献：
  名称：

  WO2007/8037

  摘要：

  公开号：

文献信息

• Visible-Light-Driven Alkyne Hydro-/Carbocarboxylation Using CO₂via Iridium/Cobalt Dual Catalysis for Divergent Heterocycle Synthesis
  作者：Jing Hou、Aloysius Ee、Wei Feng、Jin-Hui Xu、Yu Zhao、Jie Wu

  DOI：10.1021/jacs.8b01561

  日期：2018.4.18

  We present herein the first visible-light-driven hydrocarboxylation as well as carbocarboxylation of alkynes using CO2 via an iridium/cobalt dual catalysis. Such transformations provide access to various pharmaceutically important heterocycles in a one-pot procedure from readily available alkynes. Coumarins, 2-quinolones, and 2-benzoxepinones were directly accessed through a one-pot alkyne hydrocarboxylation/alkene

  我们在此展示了第一个可见光驱动的烃羧化以及通过铱/钴双催化使用 CO2 的炔烃的羧化。这种转化提供了通过一锅法从容易获得的炔烃获得各种药学上重要的杂环的途径。通过一锅炔烃加氢羧化/烯烃异构化/环化序列直接获得香豆素、2-喹诺酮和 2-苯并氧杂环酮，其中 Ir 光催化剂起到双重作用，促进炔烃加氢羧化中的单电子转移和随后的能量转移烯烃异构化。此外，前所未有的钴羧化/酰基迁移级联使炔双官能化能够高效引入γ-羟基丁烯内酯。
• A Cascade Reaction Actuated by Nucleophilic Heterocyclic Carbene Catalyzed Intramolecular Addition of Enals via Homoenolate to α,β-Unsaturated Esters: Efficient Synthesis of Coumarin Derivatives
  作者：C. R. Sinu、D. V. M. Padmaja、U. P. Ranjini、K. C. Seetha Lakshmi、Eringathodi Suresh、Vijay Nair

  DOI：10.1021/ol303091m

  日期：2013.1.4

  A nucleophilic heterocyclic carbene mediated intramolecular homoenolate reaction strategy for the efficient synthesis of 4-alkyl substituted coumarins is described.

  描述了有效合成4-烷基取代的香豆素的亲核杂环卡宾介导的分子内均烯酸酯反应策略。
• Prostaglandin reductase inhibitors
  申请人：Lin Rong-Hwa

  公开号：US20090124688A1

  公开（公告）日：2009-05-14

  A method of inhibiting 15-keto prostaglandin-Δ 13 -reductase 2 by contacting 15-keto prostaglandin-Δ 13 -reductase 2 with an aryl compound of Formula (I), (II), (III), or (IV) shown herein. Also disclosed are methods of treating peroxisome proliferators-activated receptor related diseases and lowering blood glucose levels by administering to a subject in need thereof an effective amount of such an aryl compound.

  本发明涉及一种通过将公式（I），（II），（III）或（IV）的芳基化合物与15-酮前列腺素-Δ13-还原酶2接触来抑制15-酮前列腺素-Δ13-还原酶2的方法。本发明还公开了通过向需要的受试者施用有效量的这种芳基化合物来治疗过氧化物酶体增殖物活化受体相关疾病和降低血糖水平的方法。
• Photosynthesis of 3-Alkylated Coumarins from Carboxylic Acids Catalyzed by a Na₂S-Based Electron Donor–Acceptor Complex
  作者：Hai-Yang Song、Mei-Yi Liu、Jing Huang、Dan Wang、Jun Jiang、Jin-Yang Chen、Tian-Bao Yang、Wei-Min He

  DOI：10.1021/acs.joc.2c02679

  日期：2023.2.17

  strategy to synthesize various 3-alkylated coumarins from easily available coumarins and naturally abundant carboxylic acids under photocatalyst-, oxidant-, and additive-free and mild conditions is reported. Using Na2S as the catalytic electron donor, a series of primary, secondary, and tertiary carbon radicals can be efficiently generated, and the EDA complex can be regenerated without an alkaline additive

  报道了一种简单实用的电子供体-受体 (EDA) 策略，可在无光催化剂、氧化剂和添加剂的温和条件下，从易得的香豆素和天然丰富的羧酸中合成各种 3-烷基化香豆素。以Na 2 S为催化电子供体，可高效生成一系列伯、仲、叔碳自由基，无需碱性添加剂即可再生EDA络合物。
• WO2007/8037
  申请人：——

  公开号：——

  公开（公告）日：——