c-5-(N-phenethylcarbamoyl)-1,3,5-trimethyl-r-1,c-3-cyclohexanedicarboxylic acid | 156571-14-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: c-5-(N-phenethylcarbamoyl)-1,3,5-trimethyl-r-1,c-3-cyclohexanedicarboxylic acid
• CAS: 156571-14-1
• 化学式: C₂₀H₂₇NO₅
• 分子量: 361.438
• InChiKey: XDXVBKKJKGEOKL-ACDBMABISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.72
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  103.7
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  c-5-(N-phenethylcarbamoyl)-1,3,5-trimethyl-r-1,c-3-cyclohexanedicarboxylic acid 在 重水 作用下， 以 乙腈 为溶剂， 生成 2-苯乙胺 、 (1R,5S,7s)-1,5,7-trimethyl-2,4-dioxo-3-oxabicyclo[3.3.1]nonane-7-carboxylic acid
  参考文献：
  名称：

  Intramolecular Acylolysis of Amide Derivatives of Kemp's Triacid: Strain Effects and Reaction Rates

  摘要：

  Intramolecular acylolysis of comparable secondary and tertiary amide derivatives of Kemp's triacid, 4, and its cis,trans isomer 5 has been examined. For both triacids, the tertiary amide derivatives undergo acylolysis about 1000 times faster than the corresponding secondary amide. Also, amide derivatives of Kemp's triacid undergo acylolysis about 100 times faster than the corresponding amide derivatives of the cis,trans isomer. Thus, acylolysis rates spanning a range of nearly 10(6) are observed. It is proposed that the large rate difference between secondary and tertiary amides in these molecules results from greater pseudoallylic (pseudo-A(1,3)) strain associated with the tertiary amides. It also is proposed that the slower acylolysis rates observed with amide derivatives of the cis,trans isomer of Kemp's triacid result from greater 1,3-diaxial strain associated with acylolysis of these compounds. The data show that both the structure of the triacid and the structure of the amide have a direct effect on the acylolysis rate. Because previous studies only focused on the structure of the triacid, the proposal that intramolecular acylolysis of amide derivatives of Kemp's triacid is a useful model system for studying enzyme catalysis (Menger, F. M.; Ladika, M. J. Am. Chem. Sec. 1988, 110, 6794. Menger, F. M, Biochemistry 1992, 31, 5368) is reexamined.

  DOI：

  10.1021/jo00092a006
• 作为产物：
  描述：

  KEMP'S TRIACID 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 190.0 ℃ 、1.33 Pa 条件下， 生成 c-5-(N-phenethylcarbamoyl)-1,3,5-trimethyl-r-1,c-3-cyclohexanedicarboxylic acid
  参考文献：
  名称：

  新 Kemp 的二酸衍生物为碱土和过渡金属离子提供有效的传输和可修改的选择性

  摘要：

  1,3,5-三甲基-r-1、c-3、c-5-环己烷三羧酸（肯普三酸）的新衍生物显示出通过氯仿液膜传输碱土金属和过渡金属离子的高效率。坎普三酸或其几何异构体的简单合成为螯合剂提供了金属阳离子的三足结合位点。三足结合位点由 r-1、c-3-双轴羧基和 c-5-酰胺、酯或 C-甲基组成。碱土金属运输变化很大，对 c-5 基团的变化很敏感。对于过渡金属运输，c-5-酰胺二酸具有较高的总运输效率。对于 c-5-酯或 C-甲基二酸，较小的二价阳离子的络合减少，导致对大阳离子的选择性增加。

  DOI：

  10.1246/bcsj.70.1895