(1S,5R,7R)-1,5,7-Trimethyl-2,4-dioxo-3-oxa-bicyclo[3.3.1]nonane-7-carbonyl chloride | 185394-19-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (1S,5R,7R)-1,5,7-Trimethyl-2,4-dioxo-3-oxa-bicyclo[3.3.1]nonane-7-carbonyl chloride
• CAS: 185394-19-8
• 化学式: C₁₂H₁₅ClO₄
• 分子量: 258.702
• InChiKey: RVDPWKJXDHVWGO-CNDDSTCGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.04
• 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：
  60.44
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1S,5R,7R)-1,5,7-Trimethyl-2,4-dioxo-3-oxa-bicyclo[3.3.1]nonane-7-carbonyl chloride 以35%的产率得到
  参考文献：
  名称：

  KEMP, D. S.;PETRAKIS, K. S., J. ORG. CHEM., 1981, 46, N 25, 5140-5143

  摘要：

  DOI：
• 作为产物：
  描述：

  cis,cis-1,3,5-trimethylcyclohexane-1,3,5-tricarboxylic acid 在 氯化亚砜 作用下， 反应 3.0h， 以64%的产率得到(1S,5R,7R)-1,5,7-Trimethyl-2,4-dioxo-3-oxa-bicyclo[3.3.1]nonane-7-carbonyl chloride
  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

文献信息

• Modification of Kemp’s Triacid to Produce New Ligands Showing Efficient Alkaline Earth Metal Ion Transport with Structure Dependent Selectivity
  作者：Bruce W. Baldwin、Takuji Hirose、Zhen-He Wang、Tadafumi Uchimaru、Ari Yliniemelä

  DOI：10.1246/cl.1996.415

  日期：1996.6

  The calcium/barium selectivity ratio for efficient competitive transport among alkaline earth metal ions was controlled by structural isomerism and side chain linker changes in new lipophilic mono-substituted Kemp’s diacid ionophores.

  碱土金属离子之间有效竞争性运输的钙/钡选择性比受新型亲脂性单取代肯普二酸离子载体的结构异构和侧链接头变化的控制。
• 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.
• MENGER, F. M.;LADIKA, M., J. AMER. CHEM. SOC., 110,(1988) N 20, C. 6794-6796
  作者：MENGER, F. M.、LADIKA, M.

  DOI：——

  日期：——