8-methyl-6H-benzofuro[3,2-c]chromen-6-one | 352029-20-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 8-methyl-6H-benzofuro[3,2-c]chromen-6-one
• 英文别名: 8-Methyl-[1]benzofuro[3,2-c]chromen-6-one；8-methyl-[1]benzofuro[3,2-c]chromen-6-one
• CAS: 352029-20-0
• 化学式: C₁₆H₁₀O₃
• 分子量: 250.254
• InChiKey: QOJWVYKURKFQGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-(4-methylphenoxy)-2H-chromene-2-one 在 palladium diacetate 、 silver(l) oxide 、 sodium t-butanolate 作用下， 反应 16.0h， 以72%的产率得到8-methyl-6H-benzofuro[3,2-c]chromen-6-one
  参考文献：
  名称：

  通过双重C–H活化环化4-苯氧基-2-香豆素和2-吡喃酮

  摘要：

  通过两次C–H活化进行的芳基–杂芳基偶联是一种有力的转化，可避免安装活化基团。据报道，特权生物支架，2-香豆素和2-吡喃酮具有双重C–H活化作用。尽管这些分子框架化学性质丰富，但收率还是很高的。在吡喃酮上获得了极好的区域选择性。该方法可通过三个步骤应用于氟美阿帕林C的合成。进行了同位素效应实验，并提出了机理。

  DOI：

  10.1021/acs.orglett.6b00751

文献信息

• Copper-mediated synthesis of coumestans via C(sp 2 )-H functionalization: Protective group free route to coumestrol and 4′- O -methylcoumestrol
  作者：Mayuri M. Naik、Vijayendra P. Kamat、Santosh G. Tilve

  DOI：10.1016/j.tet.2017.07.057

  日期：2017.9

  A simple and efficient two step synthesis of coumestans is described. The key reaction in the synthesis is the use of easily available Cu(OAc)2 for CH functionalization of 3-(2-hydroxyphenyl)coumarin to give coumestan ring system via formal oxidative cyclization. This approach provided a short protective group free route to naturally occurring coumestrol and 4′-O-methylcoumestrol.

  描述了一种简单高效的香豆素两步合成法。合成中的关键反应是使用易得的Cu（OAc）2将3-（2-羟苯基）香豆素进行C H官能化，以通过正式的氧化环化反应生成Coumestan环系统。该方法为天然存在的香豆雌酚和4'- O-甲基香豆雌酚提供了一条简短的无保护基团的途径。
• One-pot two-step synthesis of 3-iodo-4-aryloxy coumarins and their Pd/C-catalyzed annulation to coumestans
  作者：Niranjan Panda、Irshad Mattan

  DOI：10.1039/c7ra12419h

  日期：——

  efficient protocol for the synthesis of various coumestans from the intramolecular annulation of 3-iodo-4-aryloxy coumarins through C–H activation has been developed. When 3-iodo-4-aryloxy coumarins were treated with 10% Pd/C (0.3 mol% Pd) in the presence of sodium acetate, the corresponding coumestans were produced in good to excellent yield. Reusability of the palladium catalyst was investigated in

  已经开发了一种通过 C-H 活化从 3-iodo-4-aryloxy 香豆素的分子内环化合成各种香豆素的有效方案。当在乙酸钠存在下用 10% Pd/C (0.3 mol% Pd) 处理 3-iodo-4-aryloxy 香豆素时，相应的香豆素以良好的产率产生。在多达三个连续循环中研究了钯催化剂的可重复使用性，发现反应的产率几乎没有改变。顺序碘化和O4-羟基香豆素的α-芳基化产生3-碘-4-芳氧基香豆素也可以在一锅两步法中以高产率从芳基碘化物开始。发现新戊酸是后一种方法生产 3-碘-4-苯氧基香豆素的最有效添加剂。带有给电子基团和吸电子基团的不同官能团也对反应条件具有耐受性。
• Palladium(II)-Catalyzed C–H Bond Activation/C–C and C–O Bond Formation Reaction Cascade: Direct Synthesis of Coumestans
  作者：Kashmiri Neog、Ashwini Borah、Pranjal Gogoi

  DOI：10.1021/acs.joc.6b01966

  日期：2016.12.2

  A palladium catalyzed cascade reaction of 4-hydroxycoumarins and in situ generated arynes has been developed for the direct synthesis of coumestans. This cascade strategy proceeds via C–H bond activation/C–O and C–C bond formations in a single reaction vessel. This methodology affords moderate to good yields of coumestans and is tolerant of a variety of functional groups including halide. The methodology

  已经开发了钯催化的4-羟基香豆素和原位生成的芳烃的级联反应，用于直接合成co烯。这种级联策略通过单个反应容器中的C–H键活化/ C–O和C–C键形成来进行。该方法提供了中等至良好的co香烯收率，并且耐受包括卤化物在内的多种官能团。该方法学应用于天然产物氟苯丙胺C的合成。
• Efficient synthesis of coumarin-based tetra and pentacyclic rings using phospha-palladacycles
  作者：Anant R. Kapdi、Amruta Karbelkar、Minal Naik、Suhas Pednekar、Christian Fischer、Carola Schulzke、Moniek Tromp

  DOI：10.1039/c3ra43821j

  日期：——

  Palladacycle 4 has proved to be an efficient catalyst for the intramolecular C–H bond functionalization of coumaryl and pyronyl ethers leading to the synthesis of tri, tetra and pentacyclic compounds, some of which were characterized by X-ray analysis. A microwave-assisted one-pot procedure for obtaining the tetracyclic rings from 4-chlorocoumarin has also been carried out. Mechanistic studies were carried out using GC, UV-Vis and ESI MS.

  Palladacycle 4 已被证明是香豆基醚和吡喃基醚分子内 C-H 键官能化的有效催化剂，可合成三环、四环和五环化合物，其中一些化合物通过 X 射线分析进行了表征。还进行了微波辅助一锅法从 4-氯香豆素获得四环。使用 GC、UV-Vis 和 ESI MS 进行了机理研究。
• [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.