trans-2-phenyl-5-carbomethoxy-1,3-dioxane | 190191-57-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: trans-2-phenyl-5-carbomethoxy-1,3-dioxane
• CAS: 190191-57-2
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: RQRGSADJJZHWAO-UMSPYCQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.52
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  trans-2-phenyl-5-carbomethoxy-1,3-dioxane 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以94.8%的产率得到trans-(6-phenyl-[1,5]-dioxane-3-yl)methanol
  参考文献：
  名称：

  Conformational Analysis of 5-Substituted 1,3-Dioxanes. 7. Effect of Lithium Bromide Addition^,1

  摘要：

  The position of equilibria, established by means of BF3, between diastereomeric cis- and trans-5-substituted-2-phenyl-1,3-dioxanes, in solvents THF and CHCl3, and in the presence of 0, 1, and 10 equiv of LiBr has been determined. The observed Delta G degrees values show that the addition of salt to the reaction medium influences the position of equilibrium. Lithium bromide effects on the conformational behavior are discussed in terms of lithium ion complexation events that lead to increased stability of the axial isomers when the substituent at C(5) is CO2H, CO2CH3, CONHCH3, and CH2OH. By contrast, disruption of the intramolecular hydrogen bond present in the axial 5-acetamido derivative (cis-9 substituent equal to NHCOCH3) modifies the preference for the axial conformation in salt-free 9 to a net dominance of the equatorial isomer in the presence of LiBr. Interpretation of the experimental observations was based on models that are apparently supported by semiempirical AM1 calculations. The results derived from the present study contribute to our understanding of the processes involved in molecular recognition and may model salt effects in physiological events.

  DOI：

  10.1021/jo9610117
• 作为产物：
  描述：

  2-phenyl-5,5-dicarbethoxy-1,3-dioxane 在 氢氧化钾 、 三乙胺 、 silver(l) oxide 作用下， 以 乙醇 为溶剂， 反应 1.67h， 生成 trans-2-phenyl-5-carbomethoxy-1,3-dioxane
  参考文献：
  名称：

  Conformational Analysis of 5-Substituted 1,3-Dioxanes. 7. Effect of Lithium Bromide Addition^,1

  摘要：

  The position of equilibria, established by means of BF3, between diastereomeric cis- and trans-5-substituted-2-phenyl-1,3-dioxanes, in solvents THF and CHCl3, and in the presence of 0, 1, and 10 equiv of LiBr has been determined. The observed Delta G degrees values show that the addition of salt to the reaction medium influences the position of equilibrium. Lithium bromide effects on the conformational behavior are discussed in terms of lithium ion complexation events that lead to increased stability of the axial isomers when the substituent at C(5) is CO2H, CO2CH3, CONHCH3, and CH2OH. By contrast, disruption of the intramolecular hydrogen bond present in the axial 5-acetamido derivative (cis-9 substituent equal to NHCOCH3) modifies the preference for the axial conformation in salt-free 9 to a net dominance of the equatorial isomer in the presence of LiBr. Interpretation of the experimental observations was based on models that are apparently supported by semiempirical AM1 calculations. The results derived from the present study contribute to our understanding of the processes involved in molecular recognition and may model salt effects in physiological events.

  DOI：

  10.1021/jo9610117