6-methyl-4-p-tolyl-2H-chromen-2-one | 93696-64-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: 6-methyl-4-p-tolyl-2H-chromen-2-one
• 英文别名: 6-Methyl-4-(4-methylphenyl)chromen-2-one
• CAS: 93696-64-1
• 化学式: C₁₇H₁₄O₂
• 分子量: 250.297
• InChiKey: OZKPLUHPLLQGEG-UHFFFAOYSA-N

物化性质

• 熔点：
  74-76 °C
• 沸点：
  416.0±24.0 °C(Predicted)
• 密度：
  1.181±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  (4-methylphenyl) 2,3-dibromo-3-(4-methylphenyl)propanoate 在 硫酸 、 三乙胺 作用下， 以 氯仿 为溶剂， 反应 0.5h， 生成 6-methyl-4-p-tolyl-2H-chromen-2-one
  参考文献：
  名称：

  Natarajan, M.; Manimaran, T.; Ramakrishnan, V. T., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1984, vol. 23, # 6, p. 529 - 534

  摘要：

  DOI：

文献信息

• Palladium catalyzed Heck-arylation/cyclization cascade: An environmentally benign and efficient synthesis of 4-arylcoumarins in water
  作者：Junmin Chen、Wei Liu、Liandi Zhou、Yongli Zhao

  DOI：10.1016/j.tetlet.2018.05.032

  日期：2018.6

  An environmentally benign and efficient approach for the synthesis of 4-arylcoumarins from ortho-hydroxy cinnamate ester derivatives with aryl iodides was developed in water under aerobic conditions. This transformation proceeds through a palladium catalyzed Heck-arylation/cyclization cascade reaction. The present protocol features a wide substrate scope and readily available starting materials to

  在水中好氧条件下，开发了一种环境友好，有效的方法，由邻羟基肉桂酸酯衍生物与芳基碘化物合成4-芳基香豆素。该转化通过钯催化的Heck-芳基化/环化级联反应进行。本方案具有广泛的底物范围和容易获得的起始材料，以高至优异的产率提供所需的产物。
• Palladium-catalyzed Suzuki–Miyaura couplings of potassium aryl trifluoroborates with 4-tosyloxycoumarins or 4-tosyloxyquinolin-2(1H)-one
  作者：Jie Wu、Liang Zhang、Hong-Guang Xia

  DOI：10.1016/j.tetlet.2006.01.020

  日期：2006.3

  Pd(PPh3)4 catalyzed Suzuki–Miyaura cross-coupling reactions of 4-tosyloxycoumarins or 4-tosyloxyquinolin-2(1H)-one with various potassium aryl trifluoroborates afforded the corresponding 4-substituted coumarins or 4-substituted quinolin-2(1H)-ones in good to excellent yield.

  Pd（PPh 3）4催化4-甲苯磺酰香豆素或4-甲苯磺酰喹啉-2（1 H）-之一与各种芳基三氟硼酸钾盐的Suzuki-Miyaura交叉偶联反应，得到相应的4-取代香豆素或4-取代喹啉-2（ 1 H）-良至优异的收率。
• A Convenient Solid-Phase Synthesis of Coumarins by TMSOTf-Catalyzed Intramolecular Seleno-Arylation of Tethered Alkenes
  作者：E. Tang、Wen Li、Zhangyong Gao

  DOI：10.1055/s-0031-1290618

  日期：2012.4

  performed using polystyrene-supported succinimidyl selenide as the selenium source. This catalytic process provides an efficient method for the regioselective synthesis of dihydrocoumarins possessing a seleno functionality, followed by syn elimination of selenoxides to provide coumarins in good yields and purities. Suzuki cross-coupling reaction of the resin-bound bromodihydrocoumarin was also performed

  使用聚苯乙烯负载的琥珀酰亚胺亚硒酸酯作为硒源，进行TMSOTf催化的链状烯烃分子内硒基芳基化反应。该催化方法为区域选择性合成具有硒代功能的二氢香豆素提供了一种有效的方法，随后同步消除亚硒酸盐以提供高收率和纯度的香豆素。还进行了树脂结合的溴代二氢香豆素的Suzuki交叉偶联反应，并且通过随后裂解硒连接基获得联苯香豆素。 硒-环化-TMSOTf-香豆素-固相合成-碳-碳键形成-催化
• Pd-catalyzed chemo-selective mono-arylations and bis-arylations of functionalized 4-chlorocoumarins with triarylbismuths as threefold arylating reagents
  作者：Maddali L.N. Rao、Abhijeet Kumar

  DOI：10.1016/j.tet.2014.07.059

  日期：2014.9

  4-chlorocoumarins were studied under palladium catalysis using triarylbismuths as threefold arylating reagents. The high reactivity of 4-chlorocoumarins was demonstrated delivering mono- and bis-arylation products in a chemo-selective manner. The reaction conditions employed are simple, robust and the threefold coupling reactivity of triarylbismuth reagents was witnessed with good to high yields in 2–4 h conditions

  在钯催化下，使用三芳基铋作为三重芳基化试剂，研究了不同取代的4-氯香豆素的交叉偶联反应。证明了4-氯香豆素的高反应性以化学选择性方式递送单芳基化和双芳基化产物。所采用的反应条件简单，稳定，并且在2-4小时的条件下，三芳基铋试剂的三重偶联反应性得到了良好的证明。在合成一些天然存在的新黄酮（3.27 – 3.30）中探索了该方法的实用性。另外，4-芳基香豆素3.1产物是制备（R）-托特罗定的有用前体。
• Heck and oxidative boron Heck reactions employing Pd(II) supported amphiphilized polyethyleneimine‐functionalized MCM‐41 (MCM‐41@aPEI‐Pd) as an efficient and recyclable nanocatalyst
  作者：Seyed Farshad Motevalizadeh、Masoumeh Alipour、Fatemeh Ashori、Alireza Samzadeh‐Kermani、Hosein Hamadi、Mohammad Reza Ganjali、Hamideh Aghahosseini、Ali Ramazani、Mehdi Khoobi、Elham Gholibegloo

  DOI：10.1002/aoc.4123

  日期：2018.3

  MCM‐41@PEI‐dodecane and the resulted MCM‐41@aPEI‐Pd nanocatalyst was characterized by FT‐IR, TEM, ICP‐AES and XPS. Our designed nanocatalyst with a distinguished core‐shell structure and Pd2+ ions as catalytic centers was explored as an efficient and recyclable catalyst for Heck and oxidative boron Heck coupling reactions. In Heck coupling reaction, the catalytic activity of MCM‐41@aPEI‐Pd in the presence of triethylamine

  基于MCM-41与聚乙烯亚胺（PEI）的共价表面官能化，基于[3-（2,3-环氧丙氧基）丙基]三甲氧基硅烷（EPO）作为交联剂，开发了一种新型纳米催化剂。然后将MCM-41表面的胺官能团与碘十二烷共轭，使催化剂具有两亲性质。钯（II）最终被固定在MCM-41 @ PEI-十二烷上，并通过FT-IR，TEM，ICP-AES和XPS对所得的MCM-41 @ aPEI-Pd纳米催化剂进行了表征。我们设计的纳米催化剂具有出色的核壳结构和Pd 2+离子作为催化中心被研究为Heck和氧化硼Heck偶联反应的一种有效且可回收的催化剂。在Heck偶联反应中，以三乙胺为碱的MCM-41 @ aPEI-Pd的催化活性导致很高的收率和选择性。同时，在香豆素的C-4区域选择性芳基化中，通过直接C-H活化研究了MCM-41 @ aPEI-Pd作为第一种半均相钯催化剂，对不同的官能团获得了中等至优异的收率。浸出试验表明，MCM-41