5,6,7-trimethoxy-4-phenyl-2H-chromen-2-one | 111584-38-4

• 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: 5,6,7-trimethoxy-4-phenyl-2H-chromen-2-one
• 英文别名: 4-phenyl-5,6,7-trimethoxycoumarin；5,6,7-trimethoxy-4-phenylcoumarin；5,6,7-trimethoxy-4-phenyl-coumarin；5,6,7-Trimethoxy-4-phenyl-cumarin；4-phenyl-5,6,7-trimethoxy coumarin；5,6,7-Trimethoxy-4-phenylchromen-2-one
• CAS: 111584-38-4
• 化学式: C₁₈H₁₆O₅
• 分子量: 312.322
• InChiKey: YIMYZIOJBXYINI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5,6,7-trimethoxy-4-phenyl-2H-chromen-2-one 在 sodium hydroxide 、 mercury(II) oxide 作用下， 生成 4,5,6-trimethoxy-3-phenyl-benzofuran-2-carboxylic acid
  参考文献：
  名称：

  Ahluwalia et al., Proceedings - Indian Academy of Sciences, Section A, 1959, # 49, p. 104,107

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4,5-三甲氧基苯酚 在 palladium diacetate 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 5,6,7-trimethoxy-4-phenyl-2H-chromen-2-one
  参考文献：
  名称：

  New Method for Preparation of Coumarins and Quinolinones via Pd-Catalyzed Intramolecular Hydroarylation of C−C Triple Bonds

  摘要：

  A new and general method has been developed for preparation of coumarins and quinolinones by intramolecular hydroarylation of alkynes. Various aryl alkynoates and alkynanilides undergo fast intramolecular reaction at room temperature in the presence of a catalytic amount of Pd(OAc)(2) in a mixed solvent containing trifluoroacetic acid (TFA), affording coumarins and quinolinones in moderate to excellent yields with more than 1000 turnover numbers (TON) to Pd. The methodology proved to tolerate a number of functional groups such as Br and CHO. On the basis of isotope experiments, a possible mechanism involving ethynyl chelation-assisted electrophilic metalation of aromatic C-H bonds by in-situ generated cationic Pd(II) species has been discussed. Also the involvement of vinylcationic species has been suggested.

  DOI：

  10.1021/jo000861q

文献信息

• Pd^II-Catalyzed Reaction of Phenols with Propiolic Esters. A Single-Step Synthesis of Coumarins
  作者：Tsugio Kitamura、Kiyomi Yamamoto、Masashi Kotani、Juzo Oyamada、Chengguo Jia、Yuzo Fujiwara

  DOI：10.1246/bcsj.76.1889

  日期：2003.10

  The intermolecular reaction of phenols with propiolic esters in TFA in the presence of a Pd(OAc)2 catalyst, affording coumarin derivatives, is described. An exclusive formation of 5,6,7-trimethoxy-...

  描述了在 Pd(OAc)2 催化剂存在下，苯酚与丙炔酸酯在 TFA 中的分子间反应，得到香豆素衍生物。5,6,7-三甲氧基-...
• Process for performing an isolated Pd(II)-mediated oxidation reaction
  申请人：Moeller D. Kevin

  公开号：US20060205959A1

  公开（公告）日：2006-09-14

  There is disclosed a process for performing an isolated Pd(II) mediated oxidation reaction electrochemically. The inventive process is performed on an electrode array device having a plurality of separately addressable electrodes. Preferably, the Pd(II) mediated oxidation is a Wacker reaction. Specifically, there is disclosed a process for conducting an isolated Pd(II) mediated oxidation on a plurality of electrodes, comprising providing an electrode array device having a plurality of electrodes with a conductive electrode surface and a matrix or coating material over the electrodes surfaces; providing a solution bathing the electrode array matrix or coating material and electrode surfaces, wherein the solution comprises a transition metal species and a confining agent; and biasing one or a plurality of electrodes (“selected electrode or electrodes”) with a voltage or current to regenerate the transition metal species required for the isolated Pd(II) mediated oxidation, whereby the confining agent limits diffusion of the transition metal species to a volume surrounding each selected electrode surface.

  所披露的是一种用电化学方法进行隔离的Pd(II)催化的氧化反应的过程。该发明过程是在具有多个独立寻址电极的电极阵列设备上进行的。优选地，Pd(II)催化的氧化是一种Wacker反应。具体来说，所披露的是一种在多个电极上进行的隔离Pd(II)催化的氧化过程，包括提供一个具有多个电极的电极阵列设备，电极具有导电电极表面和覆盖在电极表面的基质或涂层材料；提供一个溶液来浸泡电极阵列基质或涂层材料和电极表面，其中该溶液包含过渡金属物种和限制剂；以及偏置一个或多个电极（“选定电极或电极”）以电压或电流再生进行隔离Pd(II)催化的氧化所需的过渡金属物种，从而限制剂限制了过渡金属物种向包围每个选定电极表面的体积内的扩散。
• Direct Synthesis of Coumarins by Pd(II)-Catalyzed Reaction of Alkoxyphenols and Alkynoates
  作者：Juzo Oyamada、Chengguo Jia、Yuzo Fujiwara、Tsugio Kitamura

  DOI：10.1246/cl.2002.380

  日期：2002.3

  Reaction of alkoxyphenols and alkynoates in the presence of a catalytic amount of Pd(OAc)2 in trifluoroacetic acid at room temperature gave coumarin derivatives in high yields. This procedure provides a convenient method for direct synthesis of coumarin derivatives under very mild conditions.

  在催化量的 Pd(OAc) 2 在三氟乙酸中的存在下，烷氧基苯酚和炔酸酯在室温下反应以高产率得到香豆素衍生物。该程序为在非常温和的条件下直接合成香豆素衍生物提供了一种方便的方法。
• Donnelly, Dervilla M.X.; Busteed, Roslynn; Kenny, Peter M., Heterocycles, 1989, vol. 28, # 1, p. 411 - 419
  作者：Donnelly, Dervilla M.X.、Busteed, Roslynn、Kenny, Peter M.、Polonsky, Judith、Finet, Jean-Pierre、Prange, Thierry

  DOI：——

  日期：——
• US7507837B2
  申请人：——

  公开号：US7507837B2

  公开（公告）日：2009-03-24