3-hydroxy-7,9-dimethoxy-1-methyl-6H-benzo[c]chromen-6-one | 62827-47-8

• 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: 3-hydroxy-7,9-dimethoxy-1-methyl-6H-benzo[c]chromen-6-one
• 英文别名: alternariol 2,4-dimethyl ether；alternariol dimethyl ether；alternariol-7,9-dimethyl ether；ADME；3-hydroxy-7,9-dimethoxy-1-methyl-benzo[c]chromen-6-one；3-Hydroxy-7,9-dimethoxy-1-methyl-benzo[c]chromen-6-on；Alternariol 2,4-dimethyl ether；3-hydroxy-7,9-dimethoxy-1-methylbenzo[c]chromen-6-one
• CAS: 62827-47-8
• 化学式: C₁₆H₁₄O₅
• 分子量: 286.284
• InChiKey: YLWPIKMCIOUJLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-hydroxy-7,9-dimethoxy-1-methyl-6H-benzo[c]chromen-6-one 在 咪唑 、 水 、 三溴化硼 、 potassium hydroxide 、 silver(l) oxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 66.0h， 生成 3-O-β-D-glucopyranosyl-7-hydroxy-9-methoxy-1-methyl-6H-dibenzo[b,d]pyran-6-one
  参考文献：
  名称：

  Total synthesis of masked Alternaria mycotoxins—sulfates and glucosides of alternariol (AOH) and alternariol-9-methyl ether (AME)

  摘要：

  The synthesis of different protected alternariol derivatives using intramolecular cyclization of iodoresorcylic acid phenyl esters by palladium-catalyzed C-H activation as key step is presented. Furthermore, chemical sulfation and glucosylation were applied for the preparation of conjugated Alternaria mycotoxins. These compounds are suspected to be formed during metabolism in contaminated plants. Therefore, all synthetic conjugates prepared within this work serve as reference materials for further studies in the fields of bioanalytics and toxicology of mycotoxins. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.10.008
• 作为产物：
  描述：

  2-iodo-4,6-dimethoxybenzoic acid 在 4-二甲氨基吡啶 、 palladium diacetate 、 potassium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基乙酰胺 为溶剂， 反应 24.75h， 生成 3-hydroxy-7,9-dimethoxy-1-methyl-6H-benzo[c]chromen-6-one
  参考文献：
  名称：

  Total synthesis of masked Alternaria mycotoxins—sulfates and glucosides of alternariol (AOH) and alternariol-9-methyl ether (AME)

  摘要：

  The synthesis of different protected alternariol derivatives using intramolecular cyclization of iodoresorcylic acid phenyl esters by palladium-catalyzed C-H activation as key step is presented. Furthermore, chemical sulfation and glucosylation were applied for the preparation of conjugated Alternaria mycotoxins. These compounds are suspected to be formed during metabolism in contaminated plants. Therefore, all synthetic conjugates prepared within this work serve as reference materials for further studies in the fields of bioanalytics and toxicology of mycotoxins. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.10.008

文献信息

• Leeper, Finian J.; Staunton, James, Journal of the Chemical Society. Perkin transactions I, 1984, # 5, p. 1053 - 1059
  作者：Leeper, Finian J.、Staunton, James

  DOI：——

  日期：——
• Raistrick et al., Biochemical Journal, 1953, vol. 55, p. 421,432
  作者：Raistrick et al.

  DOI：——

  日期：——