2,3,8,9-tetramethoxy-6H-benzo[c]chromen-6-one | 958235-82-0

• 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: 2,3,8,9-tetramethoxy-6H-benzo[c]chromen-6-one
• 英文别名: 2,3,8,9-tetramethoxydibenzo[b,d]pyran-6-one；2,3,8,9-Tetramethoxybenzo[c]chromen-6-one
• CAS: 958235-82-0
• 化学式: C₁₇H₁₆O₆
• 分子量: 316.31
• InChiKey: ATBPWDORMZDQML-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3,8,9-tetramethoxy-6H-benzo[c]chromen-6-one 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 生成 2,3,8,9-tetrahydroxybenzo[c]chromen-6-one
  参考文献：
  名称：

  鞣花酸衍生物的DNA回旋酶抑制活性。

  摘要：

  发现鞣花酸以与萘啶酸大致相同的效力抑制大肠杆菌DNA促旋酶超螺旋。合成了鞣花酸的三环类似物，其羟基的数量和位置以及它们被卤素取代的程度都不同。讨论了这些类似物的生物学活性。

  DOI：

  10.1016/s0960-894x(97)10197-4
• 作为产物：
  描述：

  3,4-二甲氧基苯酚 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium acetate 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基乙酰胺 为溶剂， 生成 2,3,8,9-tetramethoxy-6H-benzo[c]chromen-6-one
  参考文献：
  名称：

  鞣花酸衍生物的DNA回旋酶抑制活性。

  摘要：

  发现鞣花酸以与萘啶酸大致相同的效力抑制大肠杆菌DNA促旋酶超螺旋。合成了鞣花酸的三环类似物，其羟基的数量和位置以及它们被卤素取代的程度都不同。讨论了这些类似物的生物学活性。

  DOI：

  10.1016/s0960-894x(97)10197-4

文献信息

• Cu(I)-mediated lactone formation in subcritical water: a benign synthesis of benzopyranones and urolithins A–C
  作者：Prattya Nealmongkol、Kassrin Tangdenpaisal、Somkid Sitthimonchai、Somsak Ruchirawat、Nopporn Thasana

  DOI：10.1016/j.tet.2013.08.045

  日期：2013.11

  Benzopyranones were successfully synthesized using Cu(I)-mediated C-O bond formation in subcritical water. A number of benzopyranone derivatives including polymethoxy benzopyranones, benzopyranopyridones, cbromenoindolones, and furochromenones were synthesized in satisfactory yield. This methodology was further applied to synthesize the intestinal microbial metabolites, urolithins A, B, and C, which were found to exhibit potent antioxidant activity. (C) 2013 Elsevier Ltd. All rights reserved.
• Copper(I)-Mediated and Microwave-Assisted C_aryl−O_carboxylic Coupling:  Synthesis of Benzopyranones and Isolamellarin Alkaloids
  作者：Nopporn Thasana、Rattana Worayuthakarn、Phithakpong Kradanrat、Elliot Hohn、Lauren Young、Somsak Ruchirawat

  DOI：10.1021/jo701599g

  日期：2007.11.1

  [Graphics]A simple and highly effective C-O-carboxylic coupling reaction catalyzed by copper(l) salts has been developed to synthesize benzopyranones. The reaction of various 2-halobiarylcarboxylic acids was examined using microwave irradiation. A new class of pyrroloisoquinoline alkaloid, isolamellarin, was synthesized based on the annulation of dihydroisoquinoline with aryl pyruvates under basic condition and Cu-mediated/MW-assisted C-O-carboxylic lactonization.
• 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.