methyl 2-methyl-c-5-ethyl-1,3-dioxane-r-2-carboxylate | 928821-49-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-methyl-c-5-ethyl-1,3-dioxane-r-2-carboxylate
• CAS: 928821-49-2
• 化学式: C₉H₁₆O₄
• 分子量: 188.224
• InChiKey: NKXGTCKEZKRUJR-OTSSQURYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.95
• 重原子数：
  13.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl 2-methyl-c-5-ethyl-1,3-dioxane-r-2-carboxylate 在 sodium tetrahydroborate 、 lithium chloride 作用下， 生成
  参考文献：
  名称：

  Conformational analysis and selective hydrolysis of 2,5-disubstituted-1,3-dioxane-2-carboxylic acid esters

  摘要：

  5-Alkyl-2-methyl-2-carbomethoxy-1,3-dioxanes were found to have a cis preferential configuration in the equilibrium state, and the ester hydrolysis rate of the trans-isomers was faster than that of the cis-isomers. Conformational analysis and charge calculation of the carbomethoxy group in both dioxanes elucidated this selectivity. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.12.117
• 作为产物：
  描述：

  乙基丙二酸二乙酯 在 sodium tetrahydroborate 、 三氟化硼乙醚 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醇 、 甲苯 为溶剂， 生成 methyl 2-methyl-c-5-ethyl-1,3-dioxane-r-2-carboxylate
  参考文献：
  名称：

  Conformational analysis and selective hydrolysis of 2,5-disubstituted-1,3-dioxane-2-carboxylic acid esters

  摘要：

  5-Alkyl-2-methyl-2-carbomethoxy-1,3-dioxanes were found to have a cis preferential configuration in the equilibrium state, and the ester hydrolysis rate of the trans-isomers was faster than that of the cis-isomers. Conformational analysis and charge calculation of the carbomethoxy group in both dioxanes elucidated this selectivity. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.12.117

文献信息

• Esters of 2,5-multisubstituted-1,3-dioxane-2-carboxylic acid: their conformational analysis and selective hydrolysis
  作者：Tetsuji Harabe、Takatoshi Matsumoto、Takayuki Shioiri

  DOI：10.1016/j.tet.2009.02.076

  日期：2009.5

  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.