2-((tert-butyldimethylsilyl)oxy)-3,4,5-trimethoxybenzaldehyde | 1601474-95-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-((tert-butyldimethylsilyl)oxy)-3,4,5-trimethoxybenzaldehyde
• CAS: 1601474-95-6
• 化学式: C₁₆H₂₆O₅Si
• 分子量: 326.465
• InChiKey: OOBSELZHVQGIRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.91
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-((tert-butyldimethylsilyl)oxy)-3,4,5-trimethoxybenzaldehyde 在 重铬酸吡啶 、 碘 、 magnesium 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 17.0h， 生成 (2-(tert-butyldimethylsilyloxy)-3,4,5-trimethoxyphenyl)(3-(tert-butyldimethylsilyloxy)-4-methoxyphenyl)methanone
  参考文献：
  名称：

  Antimitotic and vascular disrupting agents: 2-Hydroxy-3,4,5-trimethoxybenzophenones

  摘要：

  2-Hydroxy-3,4,5-trimethoxybenzophenones (8-16) manifest pseudo-ring formation involving intramolecular hydrogen bonding of the 2-OH and the carbonyl group. Among the synthetic products described in this report, (3-hydroxy-4-methoxyphenyl)(2-hydroxy-3,4,5-trimethoxyphenyl)-methanone (14) and (3-amino-4-methoxyphenyl)(2-hydroxy-3,4,5-trimethoxy-phenyl)methanone (16) exhibit significant antiproliferative activity against KB cells with IC50 values of 11.1 and 11.3 nM, respectively. These two compounds also displayed tubulin affinity comparable to that of combretastatin A-4. In studies with human umbilical vein endothelial cells, compounds 14 and 16 revealed concentration-dependent vascular-disrupting properties. The results support the rationale of the pseudo-ring concept and suggest further investigation of A-ring modification in these benzophenones. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.02.061
• 作为产物：
  描述：

  2,3,4-三甲氧基苯甲醛 在 乌洛托品 、 硫酸 、 双氧水 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 10.5h， 生成 2-((tert-butyldimethylsilyl)oxy)-3,4,5-trimethoxybenzaldehyde
  参考文献：
  名称：

  Antimitotic and vascular disrupting agents: 2-Hydroxy-3,4,5-trimethoxybenzophenones

  摘要：

  2-Hydroxy-3,4,5-trimethoxybenzophenones (8-16) manifest pseudo-ring formation involving intramolecular hydrogen bonding of the 2-OH and the carbonyl group. Among the synthetic products described in this report, (3-hydroxy-4-methoxyphenyl)(2-hydroxy-3,4,5-trimethoxyphenyl)-methanone (14) and (3-amino-4-methoxyphenyl)(2-hydroxy-3,4,5-trimethoxy-phenyl)methanone (16) exhibit significant antiproliferative activity against KB cells with IC50 values of 11.1 and 11.3 nM, respectively. These two compounds also displayed tubulin affinity comparable to that of combretastatin A-4. In studies with human umbilical vein endothelial cells, compounds 14 and 16 revealed concentration-dependent vascular-disrupting properties. The results support the rationale of the pseudo-ring concept and suggest further investigation of A-ring modification in these benzophenones. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.02.061