2-<3-(methoxymethoxy)phenyl>-1,3-dioxane | 81245-35-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-<3-(methoxymethoxy)phenyl>-1,3-dioxane
• 英文别名: 2-[3-(Methoxymethoxy)phenyl]-1,3-dioxane
• CAS: 81245-35-4
• 化学式: C₁₂H₁₆O₄
• 分子量: 224.257
• InChiKey: GZUOPMLGAZPOQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-<3-(methoxymethoxy)phenyl>-1,3-dioxane 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 环己烷 为溶剂， 反应 0.5h， 生成 1-<<2-(1,3-dioxanyl)-6-(methoxymethoxy)phenyl>hydroxymethyl>-2,6-bis(methoxymethoxy)-4-<<(tert-butyldimethylsilyl)oxy>methyl>benzene
  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-乙酰氧基苯甲醛 在 sodium hydroxide 、 2-甲基苯磺酸 、 sodium hydride 作用下， 反应 4.58h， 生成 2-<3-(methoxymethoxy)phenyl>-1,3-dioxane
  参考文献：
  名称：

  Regioselective metallations of (methoxymethoxy)arenes

  摘要：

  DOI：

  10.1016/s0040-4020(01)91921-0

文献信息

• Synthesis and pharmacological evaluation of 1-(aminomethyl)-3,4-dihydro-5-hydroxy-1H-2-benzopyrans as dopamine D1 selective ligands
  作者：Michael R. Michaelides、Robert Schoenleber、Sheela Thomas、Diane M. Yamamoto、Donald R. Britton、Robert MacKenzie、John W. Kebabian

  DOI：10.1021/jm00114a002

  日期：1991.10

  A series of 3-substituted 1-(aminomethyl)-3,4-dihydro-5-hydroxy-1H-2- benzopyrans were prepared as potential D1 selective antagonists. The compounds were evaluated for their affinity and selectivity for the D1 receptor as well as for their functional antagonism of D1-mediated pharmacological events. The compounds show potent D1 antagonist properties in vitro. The optimum nitrogen substitution was found

  制备了一系列3-取代的1-（氨基甲基）-3，4-二氢-5-羟基-1H-2-苯并吡喃，作为潜在的D1选择性拮抗剂。评价化合物对D1受体的亲和力和选择性，以及对D1介导的药理作用的功能拮抗作用。这些化合物在体外显示出有效的D1拮抗剂特性。发现最佳的氮取代是伯胺，并且观察到的在6-位取代的效力的顺序是OH大于Br大于H大于OMe。还对体内的两种代表性化合物（6-甲基和6-溴类似物）的多巴胺能活性进行了评估。有趣的是，两种化合物均表现为有效的体内激动剂。
• Studies towards the total synthesis of mumbaistatin: synthesis of highly substituted benzophenone and anthraquinone building blocks
  作者：Florian Kaiser、Lothar Schwink、Janna Velder、Hans-Günther Schmalz

  DOI：10.1016/s0040-4020(03)00427-7

  日期：2003.4

  Model compounds and building blocks for a planned total synthesis of the highly potent glucose-6-phosphate (G6P) translocase inhibitor mumbaistatin (1) and structural analogs were elaborated: compound 1 represents a lead structure in the development of potential new antidiabetic drugs. With the model substrate 20 it was demonstrated that highly functionalized, tetra-ortho-substituted benzophenones can be prepared by nucleophilic addition of an aryllithium-building block to a benzaldehyde followed by oxidation. For compound 37, a potential precursor of the anthraquinone part of mumbaistatin, various approaches via aryne/phthalide annulations were developed and evaluated. The required functionalized arenes were prepared exploiting, among others, regioselective bromination and ortho-lithiation reactions. Coupling reactions of the anthracene-carbaldehyde 44 derived from 37 with various metalated arenes proved to be unexpectedly difficult and failed so far. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Regioselective metalation reactions of some substituted (methoxymethoxy)arenes
  作者：Mark R. Winkle、Robert C. Ronald

  DOI：10.1021/jo00132a022

  日期：1982.5
• WINKLE, M. R.;RONALD, R. C., J. ORG. CHEM., 1982, 47, N 11, 2101-2108
  作者：WINKLE, M. R.、RONALD, R. C.

  DOI：——

  日期：——
• RONALD, R. C.;WINKLE, M. R., TETRAHEDRON, 1983, 39, N 12, 2031-2042
  作者：RONALD, R. C.、WINKLE, M. R.

  DOI：——

  日期：——