dilactone of α,α'-dihydroxy-α,α'-dimethyladipic acid | 5760-70-3

• 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: dilactone of α,α'-dihydroxy-α,α'-dimethyladipic acid
• 英文别名: dilactone of α,α'-dioxy-α,α'-dimethyladipic acid；1,4-dimethyl-2,5-dioxa-bicyclo[2.2.2]octane-3,6-dione；1,4-Dimethyl-2,5-dioxa-bicyclo[2.2.2]octan-3,6-dion；1,4-Dimethyl-2,5-dioxabicyclo[2.2.2]octane-3,6-dione
• CAS: 5760-70-3
• 化学式: C₈H₁₀O₄
• 分子量: 170.165
• InChiKey: SGYLPSNSCHSPDU-UHFFFAOYSA-N

物化性质

• 沸点：
  299.5±15.0 °C(Predicted)
• 密度：
  1.334±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  dilactone of α,α'-dihydroxy-α,α'-dimethyladipic acid 在 水 作用下， 反应 2.5h， 以66%的产率得到d,l-α,α'-dihydroxy-α,α'-dimethyladipic acid
  参考文献：
  名称：

  Autoassembly of cage structures

  摘要：

  The d,l-(1a) and meso-forms (1b) of alpha,alpha'-dihydroxy-alpha,alpha'-dimethyladipic acid, dilactone (3), diiminodilactone (4), and lactonolactam (5) were obtained by the reaction of acetonylacetone with KCN and HCl. The transformations of 1 to the esters 2, dilactone 3 to 1a, and diiminodilactone 4 to dilactone 3 were studied. It was shown that 3 can be readily obtained from 1a by thermolysis, acid catalysis, and DCC action as well as by acid catalyzed cyclization of 2a, while dilactone 3 can be obtained from 1b and 2b in negligible yield only under drastic conditions, obviously, due to the partial epimirization of the meso-forms. The mild thermolysis of 1b leads to trans-lactonoacid (6), from which the ester 7 has been obtained. The effective acid catalyzed cyclization of amides 8 and 9 to 3, lactamoamide 12 to 5, and amide 14 to model lactone 13 was found. The NMR spectra of the products were studied, and a H-1 NMR test was suggested for identification of d,l- and meso-forms 1 and 2. The stereochemistry of monolactones 6, 7, 9, 10a, 10b, 11 and dilactone 3 was established. The differences in the chemical behavior of alpha,alpha'-dihydroxyglutaric and adipic acids were explained by the significant reduction of the non-bonded interactions to the substituents in the corresponding monolactones during the transfer from 1,3- to 1,4-substituted systems.

  DOI：

  10.1007/bf00699832
• 作为产物：
  描述：

  1,4-dimethyl-2,5-dioxabicyclo[2.2.2]octane-3,6-diimine 在 盐酸 作用下， 以 乙醚 为溶剂， 反应 240.0h， 以90%的产率得到dilactone of α,α'-dihydroxy-α,α'-dimethyladipic acid
  参考文献：
  名称：

  Autoassembly of cage structures

  摘要：

  The d,l-(1a) and meso-forms (1b) of alpha,alpha'-dihydroxy-alpha,alpha'-dimethyladipic acid, dilactone (3), diiminodilactone (4), and lactonolactam (5) were obtained by the reaction of acetonylacetone with KCN and HCl. The transformations of 1 to the esters 2, dilactone 3 to 1a, and diiminodilactone 4 to dilactone 3 were studied. It was shown that 3 can be readily obtained from 1a by thermolysis, acid catalysis, and DCC action as well as by acid catalyzed cyclization of 2a, while dilactone 3 can be obtained from 1b and 2b in negligible yield only under drastic conditions, obviously, due to the partial epimirization of the meso-forms. The mild thermolysis of 1b leads to trans-lactonoacid (6), from which the ester 7 has been obtained. The effective acid catalyzed cyclization of amides 8 and 9 to 3, lactamoamide 12 to 5, and amide 14 to model lactone 13 was found. The NMR spectra of the products were studied, and a H-1 NMR test was suggested for identification of d,l- and meso-forms 1 and 2. The stereochemistry of monolactones 6, 7, 9, 10a, 10b, 11 and dilactone 3 was established. The differences in the chemical behavior of alpha,alpha'-dihydroxyglutaric and adipic acids were explained by the significant reduction of the non-bonded interactions to the substituents in the corresponding monolactones during the transfer from 1,3- to 1,4-substituted systems.

  DOI：

  10.1007/bf00699832

文献信息

• Oligomers of aziridines and N-?-aziridinoethylamides
  作者：R. G. Kostyanovskii、V. P. Leshchinskaya、R. K. Alekperov、G. K. Kadorkina、L. L. Shustova、Yu. I. �l'natanov、G. L. Gromova、A. �. Aliev、I. I. Chervin

  DOI：10.1007/bf00959886

  日期：1988.11
• Kostyanovskii, R. G.; El'natanov, Yu. I.; Leshchinskaya, V. P., Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, 1986, vol. 35, # 11, p. 2420 - 2421
  作者：Kostyanovskii, R. G.、El'natanov, Yu. I.、Leshchinskaya, V. P.、Chervin, I. I.

  DOI：——

  日期：——
• Fittig, Justus Liebigs Annalen der Chemie, 1907, vol. 353, p. 57
  作者：Fittig

  DOI：——

  日期：——
• Fittig; Lentz, Justus Liebigs Annalen der Chemie, 1907, vol. 353, p. 52
  作者：Fittig、Lentz

  DOI：——

  日期：——
• KOSTYANOVSKIJ, R. G.;LESHCHINSKAYA, V. P.;ALEKPEROV, R. K.;KADORKINA, G. +, IZV. AN CCCP. CEP. XIM.,(1988) N1, S. 2566-2575
  作者：KOSTYANOVSKIJ, R. G.、LESHCHINSKAYA, V. P.、ALEKPEROV, R. K.、KADORKINA, G. +

  DOI：——

  日期：——