(3-hydroxy-4-methoxyphenyl)(2-hydroxy-3,4,5-trimethoxyphenyl)-methanone | 1601474-87-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3-hydroxy-4-methoxyphenyl)(2-hydroxy-3,4,5-trimethoxyphenyl)-methanone
• 英文别名: (3-Hydroxy-4-methoxyphenyl)-(2-hydroxy-3,4,5-trimethoxyphenyl)methanone；(3-hydroxy-4-methoxyphenyl)-(2-hydroxy-3,4,5-trimethoxyphenyl)methanone
• CAS: 1601474-87-6
• 化学式: C₁₇H₁₈O₇
• 分子量: 334.326
• InChiKey: BFSNTMJJTHEVNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  94.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-hydroxy-3,4,5-trimethoxybenzaldehyde 在 重铬酸吡啶 、 四丁基氟化铵 、 碘 、 magnesium 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 (3-hydroxy-4-methoxyphenyl)(2-hydroxy-3,4,5-trimethoxyphenyl)-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

文献信息

• Rhodium-Catalyzed Directing-Group-Assisted Aldehydic C-H Arylations with Aryl Halides
  作者：Maddali L. N. Rao、Boddu S. Ramakrishna

  DOI：10.1002/ejoc.201700881

  日期：2017.9.15

  A broad scope for the synthesis of 2′‐substituted benzophenones was established involving directing group (OH or NHTs) assisted C–H arylation of aryl aldehydes with aryl halides under rhodium‐catalyzed conditions.

  建立了广泛的合成2'-取代的二苯甲酮的范围，涉及在铑催化的条件下，直接基团（OH或NHTs）辅助芳基醛与芳基卤化物的C–H芳基化。