3,5-bis(benzyloxy)-4-<2-(benzyloxy)-6-(1,3-dioxanyl)benzoyl>benzoic acid | 159425-58-8

• 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: 3,5-bis(benzyloxy)-4-<2-(benzyloxy)-6-(1,3-dioxanyl)benzoyl>benzoic acid
• 英文别名: 4-[2-(1,3-Dioxan-2-yl)-6-phenylmethoxybenzoyl]-3,5-bis(phenylmethoxy)benzoic acid
• CAS: 159425-58-8
• 化学式: C₃₉H₃₄O₈
• 分子量: 630.694
• InChiKey: MJBLSQQWTKCAFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  47
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3,5-bis(benzyloxy)-4-<2-(benzyloxy)-6-(1,3-dioxanyl)benzoyl>benzoic acid 在 对甲苯磺酸 作用下， 以 水 、 丙酮 为溶剂， 反应 2.0h， 以90%的产率得到4-<2-(formyl)-6-(benzyloxy)benzoyl>-3,5-bis(benzyloxy)benzoic acid
  参考文献：
  名称：

  Two Practical Syntheses of Sterically Congested Benzophenones

  摘要：

  Two efficient syntheses of the sterically congested tetraortho-substituted benzophenone portion of balanol 1 (a potent PKC inhibitor) in a protected form are described. Ortho lithiation reactions are employed for the preparation of the required 1,2,3-trisubstituted aryl aldehydes (11 and 26) and for their subsequent coupling reactions (with 6 and 23, respectively). The resulting carbinol intermediates [12, 27 and 35 (from cross coupling of 11 and 23)] were then manipulated to the corresponding benzophenonecarboxylic acids 2, 31, and 39, respectively. This chemistry is amenable to large scale synthesis, and multigram quantities of final products have been prepared.

  DOI：

  10.1021/jo00101a032
• 作为产物：
  描述：

  2-<2-formyl-3-(benzyloxy)phenyl>-1,3-dioxane 在 manganese(IV) oxide 、 sodium hydroxide 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 0.17h， 生成 3,5-bis(benzyloxy)-4-<2-(benzyloxy)-6-(1,3-dioxanyl)benzoyl>benzoic acid
  参考文献：
  名称：

  Two Practical Syntheses of Sterically Congested Benzophenones

  摘要：

  Two efficient syntheses of the sterically congested tetraortho-substituted benzophenone portion of balanol 1 (a potent PKC inhibitor) in a protected form are described. Ortho lithiation reactions are employed for the preparation of the required 1,2,3-trisubstituted aryl aldehydes (11 and 26) and for their subsequent coupling reactions (with 6 and 23, respectively). The resulting carbinol intermediates [12, 27 and 35 (from cross coupling of 11 and 23)] were then manipulated to the corresponding benzophenonecarboxylic acids 2, 31, and 39, respectively. This chemistry is amenable to large scale synthesis, and multigram quantities of final products have been prepared.

  DOI：

  10.1021/jo00101a032