4-(phenylmethyl)coumarin | 118793-50-3

• 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: 4-(phenylmethyl)coumarin
• 英文别名: 4-Benzyl-chromen-2-one；4-benzylchromen-2-one
• CAS: 118793-50-3
• 化学式: C₁₆H₁₂O₂
• 分子量: 236.27
• InChiKey: SDOWTSBECIDMNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  香豆素-3-羧酸乙酯 在 palladium on activated charcoal 盐酸 、 sodium hydroxide 、 magnesium 、 copper(I) bromide 作用下， 以 二苯醚 为溶剂， 反应 42.0h， 生成 4-(phenylmethyl)coumarin
  参考文献：
  名称：

  Patra, Amarendra; Misra, Swapan K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1988, vol. 27, # 1-12, p. 272 - 273

  摘要：

  DOI：

文献信息

• Handy Protocols using Vinyl Nosylates in Suzuki-Miyaura Cross-Coupling Reactions
  作者：Anna Dikova、Nicolas P. Cheval、Aurélien Blanc、Jean-Marc Weibel、Patrick Pale

  DOI：10.1002/adsc.201500682

  日期：2015.12.14

  Vinyl nosylates derived from 1,3-dicarbonyl compounds could be engaged in Suzuki–Myaura cross coupling reactions with aryl-, vinyl- and methylboronic acids or trifluoborate derivatives at room temperature in the presence of 2 mol% of [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) [PdCl2(dppf)]. One-pot procedures have been set up for practical and efficient nosylation–cross-coupling reactions

  在室温下，在存在2 mol％[1,1'-bis]的情况下，可以将衍生自1,3-二羰基化合物的乙烯基Nosylates与芳基，乙烯基和甲基硼酸或三氟硼酸酯衍生物进行Suzuki-Myaura交叉偶联反应（二苯基膦基）二茂铁]二氯钯（II）[PdCl 2（dppf）]。已经建立了一锅法，以进行实用，有效的烷基化-交叉偶联反应。作为便宜的新型假卤化物，壬基磺酸盐可提供非常稳定的化合物，并且在Suzuki-Myaura交叉偶联反应中非常有效（21个实例，占44-99％）。
• [Pd(PPh3)2(saccharinate)2]—general catalyst for Suzuki–Miyaura, Negishi cross-coupling and C–H bond functionalization of coumaryl and pyrone substrates
  作者：Parin Shah、M. Dolores Santana、Joaquín García、J. Luis Serrano、Minal Naik、Suhas Pednekar、Anant R. Kapdi

  DOI：10.1016/j.tet.2012.12.030

  日期：2013.2

  The potential of complex [Pd(PPh3)(2)(saccharinate)(2)] 1 in catalyzing Suzuki-Miyaura cross-coupling of 4-halo and 4-bromomethyl coumaryl and pyrone substrates with different aryl boronic acids has been explored. Excellent yields of the desired products are obtained in competitive reaction time and under relatively mild conditions. Negishi cross-coupling of 4-coumaryl tosylate with aryl and allcylzinc reagents has also been performed with good yields of the cross-coupled products obtained in most cases. Intramolecular C-H bond functionalization of coumaryl ethers also furnished very high yields of synthetically attractive tetracyclic ring systems exhibiting the potential of I as a powerful catalyst in synthetically important reactions. (C) 2012 Elsevier Ltd. All rights reserved.
• Nickel-Catalyzed Cross-Couplings of 4-Diethylphosphonooxycoumarins with Organozinc Reagents:  An Efficient New Methodology for the Synthesis of 4-Substituted Coumarins
  作者：Jie Wu、Zhen Yang

  DOI：10.1021/jo010452+

  日期：2001.11.1
• PATRA, AMARENDRA;MISRA, SWAPAN K., INDIAN J. CHEM. B., 27,(1988) N 3, C. 272-273
  作者：PATRA, AMARENDRA、MISRA, SWAPAN K.

  DOI：——

  日期：——
• IMIDIZED POLYMERS CONTAINING LUMINESCENT GROUPS AND METHOD FOR OBTAINING THEM
  申请人：ENI S.p.A.

  公开号：EP2358765A1

  公开（公告）日：2011-08-24