(E)-3-styryl-2H-chromen-2-one | 125155-08-0

• 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: (E)-3-styryl-2H-chromen-2-one
• 英文别名: Styrylcoumarin；3-[(E)-2-phenylethenyl]chromen-2-one
• CAS: 125155-08-0
• 化学式: C₁₇H₁₂O₂
• 分子量: 248.281
• InChiKey: GCSOCTSZKCXCOF-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-(2-hydroxy-2-phenylethyl)-2H-chromen-2-one 在 对甲苯磺酸 作用下， 以 溶剂黄146 为溶剂， 反应 24.0h， 以91%的产率得到(E)-3-styryl-2H-chromen-2-one
  参考文献：
  名称：

  Synthesis and photoinduced fluorescence of 3-(2-hetarylethenyl)chromen-2-ones

  摘要：

  3-(2-Hetarylethenyl)chromen-2-ones were synthesized for the first time, following two different schemes, and their spectral and photochemical properties were studied. The title compounds were found to undergo both reversible and irreversible photoinduced transformations which are accompanied by considerable change of the fluorescence pattern.

  DOI：

  10.1134/s1070428008040210

文献信息

• Bulky Selenium Ligand Stabilized <i>Trans</i> ‐Palladium Dichloride Complexes as Catalyst for Silver‐Free Decarboxylative Coupling of Coumarin‐3‐Carboxylic Acids
  作者：Neha Meena、Sunil Kumar、Vikki N. Shinde、S. Rajagopala Reddy、Himanshi、Nattamai Bhuvanesh、Anil Kumar、Hemant Joshi

  DOI：10.1002/asia.202101199

  日期：2022.2

  chlorine atom through Cl−Pd−Cl rotor. The coalescence of proton signals at elevated temperatures shows selenium inversion in the molecular rotors. The molecular rotors showed excellent efficiency as catalyst for decarboxylative Heck-coupling reaction.

  已经合成了三种新的分子转子复合物，其中 Cl-Pd-Cl 转子辐条连接到 Se-Pd-Se 轴上。分子转子显示氯原子通过 Cl-Pd-Cl 转子的旋转。高温下质子信号的合并表明分子转子中的硒反转。分子转子作为脱羧Heck偶联反应的催化剂表现出优异的效率。
• A transition-metal-free fast track to flavones and 3-arylcoumarins
  作者：Mostafa Golshani、Mehdi Khoobi、Nafiseh Jalalimanesh、Farnaz Jafarpour、Alireza Ariafard

  DOI：10.1039/c7cc02107k

  日期：——

  The procedure consists of a sequence of some reactions including an arylation/decarboxylation cascade and proceeds well in aqueous media to afford biologically interesting flavones and 3-arylcoumarins. This method exhibited excellent selectivity and functional group tolerance under mild conditions. The reaction also showed perfect efficacy for the preparation of styryl coumarins.

  使用K 2 S 2 O 8，实现了色农酮与芳基硼酸的高度区域选择性和无过渡金属的一锅芳基化反应。该程序由一系列反应组成，包括芳基化/脱羧级联，并在水性介质中进行得很好，从而提供了生物学上令人感兴趣的黄酮和3-芳基香豆素。该方法在温和条件下显示出极好的选择性和官能团耐受性。该反应还显示出制备苯乙烯基香豆素的完美功效。
• [EN] LATENT ACIDS AND THEIR USE<br/>[FR] ACIDES LATENTS ET LEUR UTILISATION
  申请人：BASF SE

  公开号：WO2016124493A1

  公开（公告）日：2016-08-11

  Compounds of the formula (I) and (IA) wherein X is -O(CO)-; R1 is C1-C12haloalkyl or C6-C10haloaryl; R2 is located in position 7 of the coumarinyl ring and is OR8; R2a, R2b and R2C independently of each other are hydrogen; R3 is C1-C8haloalkyl or C1-C8haloalkyl; R4 is hydrogen; and R8 is C1-C6alkyI; are suitable as photosensitive acid donors in the preparation of photoresist compositions such as used for example in the preparation of spacers, insulating layers, interlayer dielectric films, insulation layers, planarization layers, protecting layers, overcoat layers, banks for electroluminescence displays and liquid crystal displays (LCD).

  化合物的化学式（I）和（IA），其中X为-O(CO)-；R1为C1-C12卤代烷基或C6-C10卤代芳基；R2位于香豆素环的第7位，为OR8；R2a、R2b和R2C彼此独立地为氢；R3为C1-C8卤代烷基或C1-C8卤代烷基；R4为氢；R8为C1-C6烷基，适用于作为感光酸给体，用于制备光刻胶组合物，例如用于制备间隔层、绝缘层、层间介质膜、绝缘层、平坦化层、保护层、覆盖层、电致发光显示器和液晶显示器（LCD）的制备。
• 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。
• Palladium-Catalyzed Cross-Coupling Reaction of Diazo Compounds and Vinyl Boronic Acids: An Approach to 1,3-Diene Compounds
  作者：Yamu Xia、Ying Xia、Zhen Liu、Yan Zhang、Jianbo Wang

  DOI：10.1021/jo5012703

  日期：2014.8.15

  A palladium-catalyzed oxidative cross-coupling of vinyl boronic acids and cyclic α-diazocarbonyl compounds has been reported. The reaction constitutes an efficient method for the synthesis of 1,3-diene compounds bearing a ring structure. Mechanistically, the reaction involves migratory insertion of palladium carbene as the key step.

  已经报道了钯催化的乙烯基硼酸和环状α-重氮羰基化合物的氧化交叉偶联。该反应构成合成具有环结构的1，3-二烯化合物的有效方法。从机理上讲，该反应涉及钯卡宾的迁移插入是关键步骤。