2-<2-bromo-3-(benzyloxy)phenyl>-1,3-dioxane | 159425-38-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-<2-bromo-3-(benzyloxy)phenyl>-1,3-dioxane
• 英文别名: 2-[2-(bromo-3-(benzyloxy)phenyl)]-1,3-dioxane；2-[2-Bromo-3-(benzyloxy)phenyl]-1,3-dioxane；2-(2-bromo-3-phenylmethoxyphenyl)-1,3-dioxane
• CAS: 159425-38-4
• 化学式: C₁₇H₁₇BrO₃
• 分子量: 349.224
• InChiKey: BUCQQPRPRDIUBY-UHFFFAOYSA-N

物化性质

• 沸点：
  436.0±45.0 °C(predicted)
• 密度：
  1.376±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-<2-bromo-3-(benzyloxy)phenyl>-1,3-dioxane 在 喹啉 、 manganese(IV) oxide 、 sodium chlorite 、 正丁基锂 、 氨基磺酸 、 potassium carbonate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 乙腈 为溶剂， 反应 27.0h， 生成 4-(6-Benzyloxy-2-(benzyloxycarbonyl)benzoyl)-3,5-dibenzyloxybenzoic 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：

  3-(benzyloxy)-2-bromobenzyl alcohol 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 对甲苯磺酸 、 sodium bromide 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 4.5h， 生成 2-<2-bromo-3-(benzyloxy)phenyl>-1,3-dioxane
  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

文献信息

• Substituted fused and bridged bicyclic compounds as therapeutic agents
  申请人：Eli Lilly and Company

  公开号：US05583221A1

  公开（公告）日：1996-12-10

  Compounds having the formula ##STR1## methods for using such compounds to inhibit protein kinase C in animals, including man are useful as inhibitors of protein kinase C. Also disclosed are pharmaceutical compositions including such compounds and compounds having the formula.

  化合物的分子式为##STR1##的化合物，使用这种化合物的方法可以抑制动物中的蛋白激酶C，包括人类，这些化合物是蛋白激酶C的抑制剂。还披露了包括这些化合物和分子式的药物组合物。
• Synthesis and Protein Kinase Inhibitory Activity of Balanol Analogues with Modified Benzophenone Subunits
  作者：John W. Lampe、Christopher K. Biggers、Jean M. Defauw、Robert J. Foglesong、Steven E. Hall、Julia M. Heerding、Sean P. Hollinshead、Hong Hu、Philip F. Hughes、G. Erik Jagdmann、Mary George Johnson、Yen-Shi Lai、Christopher T. Lowden、Michael P. Lynch、José S. Mendoza、Marcia M. Murphy、Joseph W. Wilson、Lawrence M. Ballas、Kiyomi Carter、James W. Darges、Jefferson E. Davis、Frederick R. Hubbard、Mark L. Stamper

  DOI：10.1021/jm020018f

  日期：2002.6.1

  A series of analogues of the protein kinase C (PKC) inhibitory natural product balanol which bear modified benzophenone subunits are described. The analogues were designed with the goal of uncovering structure - activity features that could be used in the development of PKC inhibitors with a reduced polar character compared to balanol itself. The results of these studies suggest that most of the benzophenone features found in the natural product are important for obtaining potent PKC inhibitory compounds. However, several modifications were found to lead to selective inhibitors of the related enzyme protein kinase A (PKA), and several specific modifications to the polar structural elements of the benzophenone were found to provide potent PKC inhibitors. In particular, it was found that replacement of the benzophenone carboxylate with bioisosteric equivalents could lead to potent analogues. Further, a tolerance for lipophilic substituents on the terminal benzophenone ring was uncovered. These results are discussed in light of recently available structural information for PKA.
• SUBSTITUTED FUSED AND BRIDGED BICYCLIC COMPOUNDS AS THERAPEUTIC AGENTS
  申请人：ELI LILLY AND COMPANY

  公开号：EP0758312B1

  公开（公告）日：1999-12-22
• EP0758312A4
  申请人：——

  公开号：EP0758312A4

  公开（公告）日：1997-09-10
• US5432198A
  申请人：——

  公开号：US5432198A

  公开（公告）日：1995-07-11