2,3-dimethoxy-6H-benzo[c]chromen-6-one | 108012-00-6

• 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: 2,3-dimethoxy-6H-benzo[c]chromen-6-one
• 英文别名: 2,3-Dimethoxybenzo[c]chromen-6-one；2,3-dimethoxybenzo[c]chromen-6-one
• CAS: 108012-00-6
• 化学式: C₁₅H₁₂O₄
• 分子量: 256.258
• InChiKey: FIIAAZLCQUMWOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3,4-二甲氧基苯酚 在 palladium on activated charcoal 、 硫酸 作用下， 生成 2,3-dimethoxy-6H-benzo[c]chromen-6-one
  参考文献：
  名称：

  Cavill et al., Journal of the Chemical Society, 1958, p. 1544,1548

  摘要：

  DOI：

文献信息

• Efficient One-Pot Synthesis of Dibenzopyranones via a Decarboxylative Cross-Coupling and Lactonization Sequence
  作者：Jiaying Luo、Youling Lu、Saiwen Liu、Jing Liu、Guo-Jun Deng

  DOI：10.1002/adsc.201100338

  日期：2011.10

  A highly selective palladium bis(acetoacetonate)/copper(I) chloride [Pd(acac)2/CuCl] catalytic system for the preparation of dibenzopyranones has been developed. Tandem decarboxylative coupling and lactonization can be realized in one pot using commercially available starting materials. The reaction proceeded well for a range of different substrates.

  已经开发了用于制备二苯并吡喃酮的高选择性双（乙酰丙酮丙酮）钯/氯化铜[Pd（acac）2 / CuCl]催化体系。串联脱羧偶联和内酯化可以使用市场上可买到的原料在一锅中实现。对于一系列不同的底物，反应进行得很好。
• Cu-Catalyzed Mild C(sp²)–H Functionalization Assisted by Carboxylic Acids en Route to Hydroxylated Arenes
  作者：Joan Gallardo-Donaire、Ruben Martin

  DOI：10.1021/ja4047894

  日期：2013.6.26

  A formal Cu-catalyzed C(sp(2))-H hydroxylation assisted by benzoic acids is described. The procedure is characterized by its mild reaction conditions and wide substrate scope utilizing simple and cheap Cu catalysts, thus becoming a user-friendly and operationally simple protocol for C(sp(2))-H hydroxylation.
• Cavill et al., Journal of the Chemical Society, 1958, p. 1544,1548
  作者：Cavill et al.

  DOI：——

  日期：——
• Beugelmans, Rene; Bois-Choussy, Michele; Chastanet, Jacqueline, Heterocycles, 1993, vol. 36, # 12, p. 2723 - 2732
  作者：Beugelmans, Rene、Bois-Choussy, Michele、Chastanet, Jacqueline、Gleuher, Martine Le、Zhu, Jieping

  DOI：——

  日期：——
• Synthesis of benzo[c]chromen-6-ones via novel cyclic aryl–Pd(II)–ester enolate intermediates
  作者：Stephen R. Taylor、Alison T. Ung、Stephen G. Pyne

  DOI：10.1016/j.tet.2007.08.080

  日期：2007.11

  The examination of the palladium catalysed arylation reactions of mono-iodo derivatives of the phenyl and benzyl esters of benzoic acid, phenylacetic acid and dehydrocinnamic acid has resulted in the formation of benzo[ c] chromen-6-ones, unexpected cinnamate and succinate products and diphenyl dimers. Many of these products can be rationalised as arising from novel cyclic ArPd(II)-enolate intermediates, formed by intramolecular C-H activation by ArPd( II). Crown Copyright (c) 2007 Published by Elsevier Ltd. All rights reserved.