(1R,5S,7s)-1,5,7-trimethyl-2,4-dioxo-3-oxabicyclo[3.3.1]nonane-7-carboxylic acid | 118537-27-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1R,5S,7s)-1,5,7-trimethyl-2,4-dioxo-3-oxabicyclo[3.3.1]nonane-7-carboxylic acid
• CAS: 118537-27-2
• 化学式: C₁₂H₁₆O₅
• 分子量: 240.256
• InChiKey: WPTPSEBASGWCNK-CNDDSTCGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.36
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  80.67
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1R,5S,7s)-1,5,7-trimethyl-2,4-dioxo-3-oxabicyclo[3.3.1]nonane-7-carboxylic acid 在 4-二甲氨基吡啶 、 氯化亚砜 、 氨 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 14.0h， 生成 (1R,5S,7S)-1,5,7-Trimethyl-2,4-dioxo-3-aza-bicyclo[3.3.1]nonane-7-carboxylic acid anthracen-2-ylamide
  参考文献：
  名称：

  Molecular recognition with convergent functional groups. VI. Synthetic and structural studies with a model receptor for nucleic acid components

  摘要：

  DOI：

  10.1021/ja00185a044
• 作为产物：
  描述：

  TRIMETHYL CIS,CIS-1,3,5-CYCLOHEXANETRICARBOXYLATE 在 对甲苯磺酸 作用下， 以 xylene 为溶剂， 反应 12.0h， 生成 (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：

  Molecular recognition with convergent functional groups. VI. Synthetic and structural studies with a model receptor for nucleic acid components

  摘要：

  DOI：

  10.1021/ja00185a044

文献信息

• Intramolecular Acylolysis of Amide Derivatives of Kemp's Triacid: Strain Effects and Reaction Rates
  作者：Timothy P. Curran、Christopher W. Borysenko、Susan M. Abelleira、Renee J. Messier

  DOI：10.1021/jo00092a006

  日期：1994.7

  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.