5-methoxy-7-methyl-2H-chromen-2-one

• 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-methoxy-7-methyl-2H-chromen-2-one
• 英文别名: 5-Methoxy-7-methylchromen-2-one
• 化学式: C₁₁H₁₀O₃
• 分子量: 190.199
• InChiKey: BOHHLJIRIHJLGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-methoxy-7-methyl-2H-chromen-2-one 以20%的产率得到
  参考文献：
  名称：

  AHLUWALIA V. K.; DHINGRA S.; KAPUS K., INDIAN J. CHEM., 1979, B18, NO 1, 79-80

  摘要：

  DOI：
• 作为产物：
  描述：

  (5-methoxy-7-methyl-2-oxochromen-4-yl) 4-methylbenzenesulfonate 生成 5-methoxy-7-methyl-2H-chromen-2-one
  参考文献：
  名称：

  AHLUWALIA V. K.; DHINGRA S.; KAPUS K., INDIAN J. CHEM., 1979, B18, NO 1, 79-80

  摘要：

  DOI：

文献信息

• Experimental and Computational Investigations of the Reactions between α,β‐Unsaturated Lactones and 1,3‐Dienes by Cooperative Lewis Acid/Brønsted Acid Catalysis
  作者：Anja Weber、Martin Breugst、Jörg Pietruszka

  DOI：10.1002/ange.202008365

  日期：2020.10.12

  AbstractThe reactions of α,β‐unsaturated δ‐lactones with activated dienes such as 1,3‐dimethoxy‐1‐[(trimethylsilyl)oxy]‐1,3‐butadiene (Brassard's diene) are barely known in literature and show high potential for the synthesis of isocoumarin moieties. An in‐depth investigation of this reaction proved a stepwise mechanism via the vinylogous Michael‐products. Subsequent cyclisation and oxidation by LHMDS

  摘要α,β-不饱和δ-内酯与活化二烯如1,3-二甲氧基-1-[(三甲基硅基)氧基]-1,3-丁二烯（布拉萨二烯）的反应在文献中鲜为人知，并且显示出很高的潜力异香豆素部分的合成。对该反应的深入研究证明了通过插烯迈克尔产物的逐步机制。随后通过 LHMDS 和 DDQ 进行环化和氧化，通过三个步骤分别提供了六种 Mellein 衍生物 (30-84%) 和四种当归碱衍生物 (40-78%)。DFT 计算提供了对反应机理的深入了解并支持逐步反应理论。
• POLYMERIZABLE LIQUID CRYSTAL COMPOSITION, POLARIZED LIGHT-EMITTING COATING MATERIAL, NOVEL NAPHTHOLACTAM DERIVATIVE NOVEL COUMARIN DERIVATIVE, NOVEL NILE RED DERIVATIVE, AND NOVEL ANTHRACENE DERIVATIVE
  申请人：Kubota Yusuke

  公开号：US20130334461A1

  公开（公告）日：2013-12-19

  Provided are a polymerizable liquid crystal composition, a coating material, a medium, and a polarizing device each produced using a polymerizable liquid crystal compound and a colorant and each capable of producing polarized light suitable for polarizing devices, and also a novel naphtholactam derivative, a novel coumarin derivative, a novel Nile Red derivative, and a novel anthracene derivative each suitable for use as the colorant. Specifically provided are a polymerizable liquid crystal composition containing (A) at least one liquid crystal compound having a polymerizable functional group, (B) at least one colorant, and (C) a polymerization initiator, and a novel naphtholactam derivative of formula (IV′), a novel coumarin derivative of formula (VI′), a novel Nile Red derivative of formula (VII′), and a novel anthracene derivative of formula (VIII′) each suitable for use as the colorant (B).

  提供了一种可聚合的液晶组合物、涂料材料、介质和极化装置，每种都使用了聚合液晶化合物和颜料，并且能够产生适合于极化装置的偏振光，还提供了一种新型萘内酰胺衍生物、一种新型香豆素衍生物、一种新型尼罗红衍生物和一种新型蒽衍生物，每种都适用于用作颜料。具体提供了一种聚合液晶组合物，包含（A）至少一种具有聚合功能基团的液晶化合物，（B）至少一种颜料，和（C）聚合引发剂，以及一种适用于用作颜料（B）的新型萘内酰胺衍生物（IV′）, 一种新型香豆素衍生物（VI′）, 一种新型尼罗红衍生物（VII′）和一种新型蒽衍生物（VIII′）。
• Valorisation of phenols to coumarins through one-pot palladium-catalysed double C–H functionalizations
  作者：Giulia Brufani、Federica Valentini、Flavio Sabatelli、Benedetta Di Erasmo、Anastasiia M. Afanasenko、Chao-Jun Li、Luigi Vaccaro

  DOI：10.1039/d2gc03579k

  日期：——

  chemical production. Among the transformation of phenols, C–H functionalization is limited to a few examples with homogeneous metal-based catalysts. Herein, a robust one-pot approach for constructing C8 alkyl substituted coumarins starting from simple phenols through the palladium-catalysed double C–H functionalizations is presented. In such a combined protocol, a Pd/C was used as a heterogeneous catalyst

  酚类通过步骤和原子效率协议对于向可持续化学品生产的过渡非常重要。在酚类的转化中，C-H 官能化仅限于使用均相金属基催化剂的少数例子。本文提出了一种稳健的一锅法，用于从简单的酚类开始通过钯催化的双 C-H 官能化构建 C8 烷基取代的香豆素。在这样的组合方案中，Pd/C 首次用作非均相催化剂。所开发的方法能够使用潜在的生物质衍生酚以良好的分离产量合成结构多样的香豆素，包括天然产物。
• A New Palladium-Catalyzed Addition:  A Mild Method for the Synthesis of Coumarins
  作者：Barry M. Trost、F. Dean Toste

  DOI：10.1021/ja961107i

  日期：1996.1.1
• Atom Economy. Palladium-Catalyzed Formation of Coumarins by Addition of Phenols and Alkynoates via a Net C−H Insertion
  作者：Barry M. Trost、F. Dean Toste、Kevin Greenman

  DOI：10.1021/ja0286573

  日期：2003.4.1

  A strategy to achieve ortho substitution of phenols initiated by an ortho-palladation to create coumarins was examined. Indeed, treatment of alkynoates with electron-rich phenols in the presence of a palladium catalyst and an acid does generate coumarins. The scope of the reaction with respect to the phenol and the alkynoates is defined. With unsymmetrical aromatic substrates, generally good regioselectivity that reflects the HOMO coefficients can be observed. In the course of these studies, numerous important naturally occurring coumarins have been synthesized, including fraxinol methyl ether, ayapin, herniarin, xanthoxyletin, and alloxanthoxyletin. The fact that a Pd(0) is the precatalyst rather than a Pd(+2) species and that an acid that reduces Pd(+2) salts, formic acid, functions better than other carboxylic acids raises doubts about the initial working hypothesis. A novel mechanism involving a palladium phenoxide formed from a hydridopalladium carboxylate and phenol is invoked to rationalize the results.