(2R,5S)-2,5-Dihydroxy-2,5-dimethyl-hexanedioic acid dimethyl ester | 108967-70-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2R,5S)-2,5-Dihydroxy-2,5-dimethyl-hexanedioic acid dimethyl ester
• CAS: 108967-70-0
• 化学式: C₁₀H₁₈O₆
• 分子量: 234.249
• InChiKey: HOQLNLLSAILAMG-AOOOYVTPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.39
• 重原子数：
  16.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  93.06
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2R,5S)-2,5-Dihydroxy-2,5-dimethyl-hexanedioic acid dimethyl ester 在 对甲苯磺酸 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 26.0h， 生成
  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：

  2,5-己二酮 、 alkaline earth salt of/the/ methylsulfuric acid 在 盐酸 作用下， 以 甲醇 、 乙醚 为溶剂， 生成 (2R,5S)-2,5-Dihydroxy-2,5-dimethyl-hexanedioic acid dimethyl ester
  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

• 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：——