trans-2-phenyl-1,3-dioxan-5-ol acetate | 4141-24-6

• 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-1,3-dioxan-5-ol acetate
• 英文别名: trans-5-Acetoxy-2-phenyl-[1,3]dioxan
• CAS: 4141-24-6
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: FFRKSRUKTZVJJG-HAQNSBGRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.66
• 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-1,3-dioxan-5-ol acetate 在 甲醇 、 sodium methylate 作用下， 生成 trans-2-Phenyl-1,3-dioxan-5-ol
  参考文献：
  名称：

  Verkade; van Roon, Recueil des Travaux Chimiques des Pays-Bas, 1942, vol. 61, p. 831,840

  摘要：

  DOI：
• 作为产物：
  描述：

  5-amino-5-hydroxymethyl-2-phenyl-1,3-dioxane 在 sodium periodate 、 lithium diisopropyl amide 作用下， 以 甲醇 、 水 为溶剂， 反应 0.83h， 生成 trans-2-phenyl-1,3-dioxan-5-ol acetate
  参考文献：
  名称：

  Majewski, Marek; Gleave, D. Mark; Nowak, Pawel, Canadian Journal of Chemistry, 1995, vol. 73, # 10, p. 1616 - 1626

  摘要：

  DOI：

文献信息

• Baggett et al., Journal of the Chemical Society, 1960, p. 2574
  作者：Baggett et al.

  DOI：——

  日期：——
• Conformational Analysis of 5-Substituted 1,3-Dioxanes. 7. Effect of Lithium Bromide Addition^,¹
  作者：Eusebio Juaristi、Francisco Díaz、Geiser Cuéllar、Hugo A. Jiménez-Vázquez

  DOI：10.1021/jo9610117

  日期：1997.6.13

  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.
• Dobinson et al., Journal of the Chemical Society, 1961, p. 2338,2342
  作者：Dobinson et al.

  DOI：——

  日期：——
• Baggett et al., Chemistry and industry, 1958, p. 1229
  作者：Baggett et al.

  DOI：——

  日期：——