7-acetyl-6-methoxy-3-methyl-benzo[b]furan-2-carboxylic acid | 855162-64-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 7-acetyl-6-methoxy-3-methyl-benzo[b]furan-2-carboxylic acid
• 英文别名: 7-acetyl-6-methoxy-3-methyl-1-benzofuran-2-carboxylic acid
• CAS: 855162-64-0
• 化学式: C₁₃H₁₂O₅
• 分子量: 248.235
• InChiKey: AABRFRVYVGRSFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  76.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-acetyl-6-methoxy-3-methyl-benzo[b]furan-2-carboxylic acid 生成 1-(6-methoxy-3-methyl-benzofuran-7-yl)-ethanone semicarbazone
  参考文献：
  名称：

  Limaye; Sathe, Rasayanam, 1936, vol. 1, p. 48,54

  摘要：

  DOI：
• 作为产物：
  描述：

  8-acetyl-3-bromo-7-hydroxy-4-methylcoumarin 在 sodium hydroxide 作用下， 生成 7-acetyl-6-methoxy-3-methyl-benzo[b]furan-2-carboxylic acid
  参考文献：
  名称：

  Limaye; Sathe, Rasayanam, 1936, vol. 1, p. 48,54

  摘要：

  DOI：

文献信息

• Derivatives of benzo[b]furan. Part II. Structural studies of derivatives of 2- and 3-benzo[b]furancarboxylic acids
  作者：Aleksandra Drzewiecka、Anna E. Koziol、Tomas Pena Ruiz、Manuel Fernandez Gomez、Marta Struga、Jerzy Kossakowski、Kinga Ostrowska、Tadeusz Lis

  DOI：10.1007/s11224-012-9965-6

  日期：2012.10

  benzo[b]furan system. As indicated by the quantum-chemical calculations, the solid-state conformers for 3 and 4 (3-benzo[b]furancarboxylic acid derivatives) are the most stable ones. In contrast, the solid-state conformers of the 2-benzo[b]furancarboxylic acid derivatives (1, 2) have the energies higher than the lowest energy conformer by 1.23 and 0.69 kcal/mol, respectively. It seems that intermolecular

  合成了 2-和 3-苯并 [b] 呋喃甲酸的选定衍生物，并使用 X 射线晶体学和计算方法研究了它们的结构。一元羧酸（1-3）结晶为由 O-H···O 分子间氢键稳定的二聚体。此外，在 OH 和 C(=O)CH3 基团之间形成分子内氢键，取代芳环 (2-4)。在1-4的晶体结构中，弱C-H···O、C-H···π和C-H···Br相互作用稳定了分子的三维堆积。1的结晶钠络合物具有化学计量[Na+·1A-·1B]·1C，因此，不对称单元包含三个不同的部分1。在该络合物中，Na+阳离子是六配位的，具有强烈扭曲的四方双锥多面体。对于每个分子 1-4，在气相中获得了几种构象异构体。它是通过取代基 [COOR 和/或 C(=O)CH3，其中 R=H，CH3] 相对于刚性苯并 [b] 呋喃系统的旋转来实现的。量子化学计算表明，3 和 4（3-苯并[b]呋喃甲酸衍生物）的固态构象异构体是最稳定的。相比之下
• Synthesis and structural characterization of derivatives of 2- and 3-benzo[b]furan carboxylic acids with potential cytotoxic activity
  作者：Jerzy Kossakowski、Kinga Ostrowska、Elżbieta Hejchman、Irena Wolska

  DOI：10.1016/j.farmac.2005.05.005

  日期：2005.6

  Derivatives of 2- and 3-benzo[b]furancarboxylic acids were prepared and evaluated for their cytotoxic potential in the National Cancer Institute, Bethesda, USA. Six compounds: 7-acetyl-6-hydroxy-3-methyl-2-benzofurancarboxylic acid (2), 6-hydroxy-7-(p-methoxycinnamoyl)-3-methyl-2-benzofurancarboxylic acid (4), 5-bromo-7-hydroxy-6-methoxy-2-benzofurancarboxylic acid methyl ester (6a), 6-acetyl-5-(O-ethyl-2'-diethylamino)-2-methyl-3-benzofurancarboxylic acid methyl ester (1f), 6-(O-ethyl-2'-diethylamino)-7-p-methoxycinnamoyl)-3-methyl-2-benzofurancarboxylic acid methyl ester hydrochloride (4b), 5-bromo-7-(O-ethyl-2'-diethylamino)-6-methoxy-2-benzofurancarboxylic acid methyl ester (6b) showed significant cytotoxic activities against human cancer cell lines. In addition the crystal structures of 7-methoxy-2-benzofurancarboxylic acid methyl ester (7a) has been solved by X-ray structure analysis of single crystals.
• Okazaki, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1939, vol. 59, p. 547,549; dtsch. Ref. S. 190, 192
  作者：Okazaki

  DOI：——

  日期：——
• Two coordination modes around the Cu(II) cations in complexes with benzo[b]furancarboxylic acids
  作者：Aleksandra Drzewiecka、Anna E. Koziol、Marcin T. Klepka、Anna Wolska、Sonia B. Jimenez-Pulido、Tadeusz Lis、Kinga Ostrowska、Marta Struga

  DOI：10.1016/j.cplett.2013.01.011

  日期：2013.2

  Three Cu(II) complexes with derivatives of the benzo[b]furancarboxylic acid have been synthesized and characterized by the elemental and thermal analyses, and IR spectroscopy. The geometry of metal-ligand interaction for all compounds has been described using X-ray absorption spectroscopy and for one of them by X-ray crystallography. Two mononuclear Cu(II) complexes, with 7-acetyl-5-bromo-6-hydroxy-3-methylbenzo[b]furan-2-carboxylic and 6-acetyl-5-hydroxy-2-methylbenzo[b]furan-3-carboxylic acids, exhibit a tetra-fold coordination, CuO4. The Cu(II) cation in crystals with 7-acetyl-6-methoxy-3-methyl-benzo[b]furan-2-carboxylic acid is penta-coordinated; the bridging COO groups and ethanol molecule stabilize the dinuclear center Cu2O10. The powdered form of this complex is based on the Cu2O8 units, indicating the absence of the ethanol molecules. (C) 2013 Elsevier B.V. All rights reserved.
• Limaye; Sathe, Rasayanam, 1936, vol. 1, p. 48,54
  作者：Limaye、Sathe

  DOI：——

  日期：——