2-(1,3-Dioxan-2-yl)-6-(methoxymethoxy)benzaldehyde | 159425-41-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(1,3-Dioxan-2-yl)-6-(methoxymethoxy)benzaldehyde
• CAS: 159425-41-9
• 化学式: C₁₃H₁₆O₅
• 分子量: 252.267
• InChiKey: INPZISBLBFAIED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(1,3-Dioxan-2-yl)-6-(methoxymethoxy)benzaldehyde 在 manganese(IV) oxide 、 正丁基锂 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 17.0h， 生成 3,5-bis(methoxymethoxy)-4-<2-(methoxymethoxy)-6-(1,3-dioxanyl)benzoyl>benzyl alcohol
  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-(3-hydroxyphenyl)-1,3-dioxane 在 正丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 正己烷 、 环己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 2-(1,3-Dioxan-2-yl)-6-(methoxymethoxy)benzaldehyde
  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, All Stereoisomers, TheirN-Tosyl Analogues, and Fully Protected Ophiocordin: An Easy Route to Hexahydroazepine Cores from Garner Aldehydes
  作者：Ajay Kumar Srivastava、Gautam Panda

  DOI：10.1002/chem.200701991

  日期：2008.5.19

  (-)-balanol and all of its stereoisomers starting from easily available Garner aldehydes are described. Diastereoselective Grignard reactions on Garner aldehydes and ring-closing metatheses are the key steps for the construction of hexahydroazepine subunits. The benzophenone subunits were constructed through coupling of suitably functionalized aromatic aldehyde and bromo components. The synthetic route

  描述了从容易获得的加纳醛开始的（-）-巴拉醇及其所有立体异构体的总合成。加纳醛和闭环易位的非对映选择性格氏反应是构建六氢氮杂亚基亚基的关键步骤。二苯甲酮亚基通过适当官能化的芳族醛和溴组分的偶联而构建。合成途径构成了方便且可扩展的反应序列，以产生所有的巴拉诺尔立体异构体。进一步探索了该方法用于合成Balanol和完全保护的ophiocordin的N-甲苯磺酰基类似物的方法。
• 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
• US5583221A
  申请人：——

  公开号：US5583221A

  公开（公告）日：1996-12-10