2-phenyl-5,5-dicarboxy-1,3-dioxane | 190191-49-2

• 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: 2-phenyl-5,5-dicarboxy-1,3-dioxane
• 英文别名: 2-Phenyl-1,3-dioxane-5,5-dicarboxylic acid
• CAS: 190191-49-2
• 化学式: C₁₂H₁₂O₆
• 分子量: 252.224
• InChiKey: PJKGFVMNPJUCFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-phenyl-5,5-dicarboxy-1,3-dioxane 在 三乙胺 、 silver(l) oxide 作用下， 反应 0.67h， 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
• 作为产物：
  描述：

  2-phenyl-5,5-dicarbethoxy-1,3-dioxane 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以40.4%的产率得到2-phenyl-5,5-dicarboxy-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

文献信息

• Synthesis, cannabinoid receptor activity, and enzymatic stability of reversed amide derivatives of arachidonoyl ethanolamide
  作者：Teija Parkkari、Juha R. Savinainen、Katri H. Raitio、Susanna M. Saario、Laura Matilainen、Tuomas Sirviö、Jarmo T. Laitinen、Tapio Nevalainen、Riku Niemi、Tomi Järvinen

  DOI：10.1016/j.bmc.2006.03.051

  日期：2006.8

  Retroanandamide (2f) and its 10 analogues (la-e, 2a-e) were synthesized and evaluated for the cannabinoid receptor activation by a [S-35]GTP gamma S binding assay using rat cerebellar membranes, and Chinese hamster ovary cell membranes expressing human CB2 receptors. The primary goal of the study was to develop cannabinoid receptor agonists having improved enzymatic stability compared to endogenous N-arachidonoyl ethanolamide (AEA). Furthermore, by reversing the amide bond of AEA, the formation of arachidonic acid would be prevented. Finally, an effect of the carbonyl carbon position on the cannabinoid receptor activity was explored by synthesizing retroanandamide analogues having different chain lengths (la-e, C-19; 2a-f, C-20). All the synthesized compounds, except 2c, behaved as partial agonists for the both cannabinoid receptors. In rat brain homogenate, the reversed amides possessed significantly higher stability against FAAH induced degradation than AEA. Therefore, the reversed amide analogues of AEA may serve as enzymatically stable structural basis for the drug design based on the endogenous cannabinoids. (c) 2006 Elsevier Ltd. All rights reserved.
• 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.