methyl 2,5-dimethyl-t-5-benzyl-1,3-dioxane-r-2-carboxylate | 1160168-19-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 2,5-dimethyl-t-5-benzyl-1,3-dioxane-r-2-carboxylate
• CAS: 1160168-19-3
• 化学式: C₁₅H₂₀O₄
• 分子量: 264.321
• InChiKey: RBLAWUQQWLBDQH-SHTZXODSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.17
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  丙酮酸甲酯 、 2-benzyl-2-methyl-1,3-propanediol 在 三氟化硼乙醚 作用下， 以 甲苯 为溶剂， 反应 65.0h， 生成 methyl 2,5-dimethyl-t-5-benzyl-1,3-dioxane-r-2-carboxylate 、 methyl 2,5-dimethyl-c-5-benzyl-1,3-dioxane-r-2-carboxylate
  参考文献：
  名称：

  Esters of 2,5-multisubstituted-1,3-dioxane-2-carboxylic acid: their conformational analysis and selective hydrolysis

  摘要：

  The carbomethoxy group at the C2 position of the 25-multisubstituted 1,3-dioxanes prefers the axial conformation rather than the equatorial one due to an anomeric effect. The trans isomers of the 5-monosubstituted Compounds are more selectively hydrolyzed than the cis isomers. Based on the calculated results, hydrolysis to the trans isomers is attributed to the larger carbonyl charges of the trans than those of the cis isomers. The anomeric and homoanomeric effects will explain the axial preference of the carbomethoxy group and selective hydrolysis to the trans isomers. Furthermore, the calculated stability between the cis and trans isomers is in good agreement with the experimental results in the equilibrium state. (C) 2009 Elsevier Ltd. All rights Reserved.

  DOI：

  10.1016/j.tet.2009.02.076