2-<2-formyl-3-(benzyloxy)phenyl>-1,3-dioxane | 159425-55-5

• 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-formyl-3-(benzyloxy)phenyl>-1,3-dioxane
• 英文别名: 2-(3-benzyloxy-2-formylphenyl)-1,3-dioxane；2-[2-formyl-3-(benzyloxy)phenyl]-1,3-dioxane；2-(1,3-Dioxan-2-yl)-6-phenylmethoxybenzaldehyde
• CAS: 159425-55-5
• 化学式: C₁₈H₁₈O₄
• 分子量: 298.339
• InChiKey: GXVSSRRDHBDLNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-<2-formyl-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 6.75h， 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-bromobenzaldehyde 在 正丁基锂 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 21.75h， 生成 2-<2-formyl-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

• Total synthesis of balanol, part 2. Completion of the synthesis and investigation of the structure and reactivity of two key heterocyclic intermediates
  作者：David Tanner、Lars Tedenborg、Antonio Almario、Ingrid Pettersson、Ingeborg Csöregh、Nicholas M. Kelly、Pher G. Andersson、Thomas Högberg

  DOI：10.1016/s0040-4020(97)00167-1

  日期：1997.3

  enantioselective total synthesis of the natural product (-)-balanol (1) is described. In addition to benzophenone fragment 8, key intermediates are chiral bicyclic aziridine 3 and the corresponding epoxide 4, both of which undergo highly regio- and stereoselective nucleophilic ring-opening reactions, allowing control of the two stereogenic centres of the target molecule. The structure and reactivity

  描述了天然产物（-）-巴拉诺醇（1）的收敛对映选择性全合成。除二苯甲酮片段8外，关键的中间体是手性双环氮丙啶3和相应的环氧化物4，二者均进行高度区域和立体选择性的亲核开环反应，从而可以控制靶分子的两个立体中心。已经对3和4的结构和反应性进行了详细研究。
• 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.
• BALANOIDS
  申请人：SPHINX PHARMACEUTICALS CORPORATION

  公开号：EP0687249A1

  公开（公告）日：1995-12-20
• 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