cyclohexane-1,2-diol,nitric acid | 32342-28-2

• 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: cyclohexane-1,2-diol,nitric acid
• 英文别名: cis-1,2-bis-nitryloxy-cyclohexane；(+/-)-trans-1,2-bis-nitryloxy-cyclohexane；(+/-)-trans-1,2-Bis-nitryloxy-cyclohexan；trans-Cyclohexandiol-dinitrat
• CAS: 32342-28-2；32342-29-3；110539-10-1
• 化学式: C₆H₁₀N₂O₆
• 分子量: 206.155
• InChiKey: KDDIUDIEWSLRMQ-WDSKDSINSA-N

物化性质

• 沸点：
  286.1±20.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.71
• 重原子数：
  14.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  104.74
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  trans-1,2-cyclohexandiol 在 硝酸 、 溶剂黄146 作用下， 生成 cyclohexane-1,2-diol,nitric acid
  参考文献：
  名称：

  Formation of nitrate esters by the oxidation of alkenes and cyclopropanes with thallium(III) nitrate in pentane

  摘要：

  DOI：

  10.1021/jo00878a035

文献信息

• THE SIGNIFICANCE OF THE "MERCURINIUM ION" IN OXYMERCURATION
  作者：A. G. Brook、George F Wright

  DOI：10.1139/v51-036

  日期：1951.4.1

  The complex formed by mercuric nitrate with cyclohexene seems not to resemble similar argentous, cuprous, and platinous salt complexes, since it is stabilized by nitric acid while they are decomposed by acidic media. Furthermore, the cyclohexene – mercuric nitrate – nitric acid system is not stable as are the others in absence of air but decomposes to yield two equivalents of mercurous salt and one equivalent of formylcyclopentane. One or both of these products are presumed to be the material which earlier workers by implication defined as 1-hydroxy-2-nitratomercuricylohexane. It has now been found that this product could not have been formed under the reaction conditions used by these earlier workers. Finally the solubilization of cyclohexene in aqueous mercuric nitrate, on which the earlier workers based their concept of an alkene-mercurinium ion, does not have its counterpart in the solubilization of cyclohexene in aqueous mercuric acetate, since the rate of solution in the latter case is not faster than the rate of hydroxymercuration. In consequence there is no present evidence that such an ion is involved in oxymercuration of alkenes.

  通过硝酸汞与环己烯形成的复合物似乎与类似的银、铜和铂盐复合物不同，因为它受硝酸稳定，而它们受酸性介质分解。此外，环己烯-硝酸汞-硝酸体系在无空气存在时不稳定，但分解产生两当量的亚汞盐和一个当量的甲基环戊烷。这两种产物中的一种或两种被认为是早期研究人员通过暗示定义为1-羟基-2-硝酸汞环己烷的材料。现在发现在早期研究人员使用的反应条件下不可能形成这种产物。最后，在水合硝酸汞中环己烯的溶解，早期研究人员基于此构想了烯烃-汞离子，但在水合乙酸汞中环己烯的溶解没有类似情况，因为后者的溶解速度不比羟基汞化反应的速度快。因此，目前没有证据表明烯烃的氧汞化中涉及这种离子。
• RELATIVE STABILITIES OF THE ISOMERIC CYCLOHEXANE-1,2,3-TRIOL TRINITRATES AND 1,2-DIOL DINITRATES
  作者：W. R. Christian、C. B. Purves

  DOI：10.1139/v51-107

  日期：1951.11.1

  Of the above trinitrates, the cis-cis-cis and the cis-trans-cis isomers melted at 70° and 88°C, respectively, but the racemic cis-cis-trans form remained as a colorless viscid oil. When dissolved in excess 0.105 N aqueous–alcoholic sodium hydroxide at 20°C, the cis-cis-cis isomer hydrolyzed most rapidly but formed least nitrite, and the solution developed most color. The same isomer evolved the smallest amount of oxides of nitrogen when kept at 106°C., but was more readily detonated by shock than was the cis-trans-cis-trinitrate. The relative reactivities toward alkali and heat of the much more stable cis and tran-cyclo-hexane-1,2-diol dinitrates, which melted at 24° and 18.5°C., respectively, were as described for the trinitrates, but their relative sensitivities to shock were no less. All five compounds were new.

  上述三硝基酯化合物中，顺-顺-顺和顺-反-顺异构体的熔点分别为70°C和88°C，而消旋顺-顺-反形式保持为无色粘稠油。当在20°C时溶解于过量的0.105N水-乙醇氢氧化钠溶液中，顺-顺-顺异构体水解速度最快，但生成的亚硝酸盐最少，溶液颜色最深。当保存在106°C时，同一异构体生成的氮氧化物最少，但受到冲击更容易引起爆炸，而顺-反-顺三硝基酯则不易发生爆炸。熔点分别为24°C和18.5°C的更加稳定的顺和反环己烷-1,2-二醇二硝酸酯，其对碱和热的相对反应性与三硝基酯相同，但它们对冲击的敏感性并未降低。所有五种化合物均为新化合物。
• 524. Sugar nitrates. Part V. Removal of nitrate groups
  作者：K. S. Ennor、John Honeyman

  DOI：10.1039/jr9580002586

  日期：——
• The Action of Lithium Aluminum Hydride on Nitrate and Nitrite Esters
  作者：Louis M. Soffer、Elizabeth W. Parrotta、Jewell Di Domenico

  DOI：10.1021/ja01141a021

  日期：1952.11
• Reactions of Nitrate Esters. III. Evidence for Nitrogen-Oxygen Cleavage in Reductions with Hydrazine and Alkaline Hydrosulfides
  作者：Raymond T. Merrow、Robert W. Van Dolah

  DOI：10.1021/ja01608a065

  日期：1955.2.1