1,4-dimethyl-2-oxa-3-oxobicyclo<2.2.2>octane | 28886-59-1

• 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: 1,4-dimethyl-2-oxa-3-oxobicyclo<2.2.2>octane
• 英文别名: 1,4-dimethyl-2-oxabicyclo<2.2.2>octan-3-one；1,4-dimethyl-2-oxa-bicyclo[2.2.2]octan-3-one；1,4-Dimethyl-2-oxa-bicyclo[2.2.2]octan-3-on；1,4-Dimethyl-2-oxabicyclo[2.2.2]octan-3-one
• CAS: 28886-59-1
• 化学式: C₉H₁₄O₂
• 分子量: 154.209
• InChiKey: BYUDJWDCBGVIAW-UHFFFAOYSA-N

物化性质

• 熔点：
  40-41 °C(Solv: water (7732-18-5); ethanol (64-17-5))
• 沸点：
  141-142 °C(Press: 25 Torr)
• 密度：
  1.101±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,4-dimethyl-2-oxa-3-oxobicyclo<2.2.2>octane 在 氯化亚砜 作用下， 生成 4-Chloro-1,4-dimethylcyclohexane-1-carboxylic acid
  参考文献：
  名称：

  Ismailov, A. G.; Rustamov, M. A.; Akhmedov, A. A., Journal of Organic Chemistry USSR (English Translation), 1980, p. 64 - 69

  摘要：

  DOI：
• 作为产物：
  描述：

  4-羟基-1-甲基双环[2.2.2]辛烷-2-酮 在 硫酸 作用下， 反应 12.0h， 以70%的产率得到1,4-dimethyl-2-oxa-3-oxobicyclo<2.2.2>octane
  参考文献：
  名称：

  Geivandov, R. Kh.; Shmelev, L. V.; Andronova, N. A., Journal of Organic Chemistry USSR (English Translation), 1982, vol. 18, # 11, p. 2187

  摘要：

  DOI：

文献信息

• The Acid-catalyzed Rearrangement of Cinenic Acid. III.¹ Structure and Synthesis of the Lactonic Product
  作者：Jerrold Meinwald、Ho Chien Hwang

  DOI：10.1021/ja01568a059

  日期：1957.6
• Rustamov, M. A.; Ismailov, A. G.; Akhmedova, R. Sh., Journal of Organic Chemistry USSR (English Translation), 1992, vol. 28, # 2.1, p. 242 - 246
  作者：Rustamov, M. A.、Ismailov, A. G.、Akhmedova, R. Sh.、Salmanov, V. A.、Amirov, Sh. A.

  DOI：——

  日期：——
• Preparative Chromatography with Extreme Productivity: HPLC Preparation of an Isomerically Pure Drug Intermediate on Multikilogram Scale
  作者：Christopher J. Welch、Derek W. Henderson、David M. Tschaen、Ross A. Miller

  DOI：10.1021/op900035y

  日期：2009.5.15

  A highly productive method for HPLC preparation of 7.5 kg of an isomerically pure drug intermediate is described. The method employs an IPA/heptane eluent with a Chromegabond Nitro stationary phase, and affords an unusually large productivity of 5.5 kkd (kilograms of desired product per kilogram of stationary phase per day). Details relating to the development and execution of the separation are provided, and possibilities for further improvements are discussed.
• Autoassembly of cage structures
  作者：R. G. Kostyanovsky、Yu. I. El'natanov

  DOI：10.1007/bf00699832

  日期：1994.4

  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.
• ISMAILOV A. G.; PYCTAMOB M. A.; AXMEDOV A. A., ZH. ORGAN. XIMII, 1980, 16, HO 1, 68-73
  作者：ISMAILOV A. G.、 PYCTAMOB M. A.、 AXMEDOV A. A.

  DOI：——

  日期：——