1,1-bis(hydroperoxy)-3,3,5-trimethylcyclohexane | 1140969-63-6

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机含氧阴离子化合物
• 英文名称: 1,1-bis(hydroperoxy)-3,3,5-trimethylcyclohexane
• 英文别名: 1,1-dihydroperoxy-3,3,5-trimethylcyclohexane
• CAS: 1140969-63-6
• 化学式: C₉H₁₈O₄
• 分子量: 190.24
• InChiKey: ILPQFTYKKKDZMD-UHFFFAOYSA-N

物化性质

• 熔点：
  56-57.5 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  306.8±12.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,1-bis(hydroperoxy)-3,3,5-trimethylcyclohexane 在 硫酸 、 水 、 双氧水 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 3,3,5-三甲基环己酮
  参考文献：
  名称：

  A new property of geminal bishydroperoxides: Hydrolysis with the removal of hydroperoxide groups to form a ketone

  摘要：

  A new property of geminal bishydroperoxide was discovered: the ability to hydrolyze in acid medium in the presence of hydrogen peroxide with the formation of ketones. The most resistant to hydrolysis are the cyclic C(6)-bishydroperoxydes: at room temperature within one day they are practically not hydrolyzed; less stable is bishydroperoxycycloheptane (C(7)): in a day its one fifth part is hydrolyzed. Bishydroperoxydes with the cycles of C(8) and C(12) for the same time hydrolyzed to 80 and 90% respectively. Of the two linear bishydroperoxydes, 2,2-dihydroperoxydecane, with sterically unhindered center, is more resistant to hydrolysis than 6,6-dihydroperoxyundecane.

  DOI：

  10.1134/s1070363210080165

文献信息

• Nature Chooses Rings: Synthesis of Silicon-Containing Macrocyclic Peroxides
  作者：Ashot V. Arzumanyan、Roman A. Novikov、Alexander O. Terent’ev、Maxim M. Platonov、Valentin G. Lakhtin、Dmitry E. Arkhipov、Alexander A. Korlyukov、Vladimir V. Chernyshev、Andrew N. Fitch、Alexander T. Zdvizhkov、Igor B. Krylov、Yury V. Tomilov、Gennady I. Nikishin

  DOI：10.1021/om500095x

  日期：2014.5.12

  The reactions of 1,2-bis(dimethylchlorosilyl)ethane (1), 1,2-bis(dimethylchlorosilyl)ethene (6), and 1,2-bis(dimethylchlorosilyl)ethyne (7) with gem-bis-(hydroperoxides) 2a-h and 1,1'-bis( hydroperoxy)bis-(cycloalkyl)peroxides 4a-c were found to proceed in an unusual way. Thus, the reactions do not give the expected polymeric peroxides; instead, they produce cyclic silicon-containing peroxides containing 2, 4, or 6 silicon atoms in the ring: 9- (3a-h), 12- (5a-c), 18- (8, 12), 24- (9, 10), 27- (13), and 36-membered (11) compounds. The size of the rings produced in the reactions increases in the series 1,2-bis(dimethylchlorosilyl)ethane < 1,2-bis(dimethylchlorosilyl)ethene < 1,2-bis(dimethylchlorosilyl)ethyne. The resulting 9- and 12-membered cyclic peroxides are stable under ambient conditions. These compounds were isolated by chromatography and characterized by H-1, C-13, and Si-29 NMR spectroscopy, X-ray diffraction, elemental analysis, and high-resolution mass spectrometry. The yields vary from 77 to 95%. Structures of the larger-size rings (18-, 24-, 27-, and 36-membered peroxides) were confirmed by H-1, C-13, and Si-29 NMR spectroscopy using 2D (COSY, HSQC, and HMBC), 2D DOSY H-1, 3D H-1-Si-29 HMBC-DOSY NMR experiments, and elemental analysis.
• US9595630B2
  申请人：——

  公开号：US9595630B2

  公开（公告）日：2017-03-14