5-{Hydroxy-[2-(3,4,5-trimethoxy-phenyl)-thiophen-3-yl]-methyl}-2-methoxy-phenol | 371778-74-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5-{Hydroxy-[2-(3,4,5-trimethoxy-phenyl)-thiophen-3-yl]-methyl}-2-methoxy-phenol
• 英文别名: 5-[hydroxy-[2-(3,4,5-trimethoxyphenyl)thiophen-3-yl]methyl]-2-methoxyphenol
• CAS: 371778-74-4
• 化学式: C₂₁H₂₂O₆S
• 分子量: 402.468
• InChiKey: GPRXMZJLDTWHDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-{Hydroxy-[2-(3,4,5-trimethoxy-phenyl)-thiophen-3-yl]-methyl}-2-methoxy-phenol 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 生成 (3-Hydroxy-4-methoxy-phenyl)-[2-(3,4,5-trimethoxy-phenyl)-thiophen-3-yl]-methanone
  参考文献：
  名称：

  The synthesis and tubulin binding activity of thiophene-based analogues of combretastatin A-4

  摘要：

  A number of analogues of combretastatin A-4 (1), containing a thiophene ring interposed between the two phenyl groups, have been prepared. The synthesis of these compounds employed. a combination of palladium-mediated coupling and iodocyclization techniques. The thiophene compounds 11, 14, 18, and 19 also represent non-benzofused analogues of some recently described tubulin binding benzo[b]thiophenes 3 5. The most active thiophene compounds identified in this study were 11, 14, and 18. Overall they are less active than I but exhibit comparable activity to the most active of the benzo[b]thiophenes 3 5. A structure-activity relationship or these compounds is considered. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00436-x
• 作为产物：
  描述：

  5-碘-1,2,3-三甲氧基苯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 碘 、 叔丁基锂 、 potassium carbonate 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 5-{Hydroxy-[2-(3,4,5-trimethoxy-phenyl)-thiophen-3-yl]-methyl}-2-methoxy-phenol
  参考文献：
  名称：

  The synthesis and tubulin binding activity of thiophene-based analogues of combretastatin A-4

  摘要：

  A number of analogues of combretastatin A-4 (1), containing a thiophene ring interposed between the two phenyl groups, have been prepared. The synthesis of these compounds employed. a combination of palladium-mediated coupling and iodocyclization techniques. The thiophene compounds 11, 14, 18, and 19 also represent non-benzofused analogues of some recently described tubulin binding benzo[b]thiophenes 3 5. The most active thiophene compounds identified in this study were 11, 14, and 18. Overall they are less active than I but exhibit comparable activity to the most active of the benzo[b]thiophenes 3 5. A structure-activity relationship or these compounds is considered. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00436-x

文献信息

• The synthesis and tubulin binding activity of thiophene-based analogues of combretastatin A-4
  作者：Bernard L Flynn、Guy P Flynn、Ernest Hamel、M.Katherine Jung

  DOI：10.1016/s0960-894x(01)00436-x

  日期：2001.9

  A number of analogues of combretastatin A-4 (1), containing a thiophene ring interposed between the two phenyl groups, have been prepared. The synthesis of these compounds employed. a combination of palladium-mediated coupling and iodocyclization techniques. The thiophene compounds 11, 14, 18, and 19 also represent non-benzofused analogues of some recently described tubulin binding benzo[b]thiophenes 3 5. The most active thiophene compounds identified in this study were 11, 14, and 18. Overall they are less active than I but exhibit comparable activity to the most active of the benzo[b]thiophenes 3 5. A structure-activity relationship or these compounds is considered. (C) 2001 Elsevier Science Ltd. All rights reserved.