1-Nitrooxy-2-hexanol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-Nitrooxy-2-hexanol
• 化学式: C₆H₁₃NO₄
• 分子量: 163.174
• InChiKey: FGVUHVRIXFWTDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.75
• 重原子数：
  11.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  72.6
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  丁基环氧乙烷 在 ammonium cerium(IV) nitrate 、 四丁基硝酸铵 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以40%的产率得到1-Nitrooxy-2-hexanol
  参考文献：
  名称：

  硝酸铈铵：一种温和而有效的试剂，用于将环氧化物转化为β-硝基醇

  摘要：

  单独或在过量硝酸根离子存在下，催化量的Ce（IV）以硝酸铈铵（CAN）的形式在温和条件下能与环氧化物平稳有效地反应，从而以良好或优异的收率生产相应的β-硝基醇。

  DOI：

  10.1016/0040-4020(94)00979-5

文献信息

• Determination of the Hydroxy Nitrate Yields from the Reaction of C₂−C₆ Alkenes with OH in the Presence of NO
  作者：Jason M. O'Brien、Eva Czuba、Donald R. Hastie、Joseph. S. Francisco、Paul B. Shepson

  DOI：10.1021/jp982320z

  日期：1998.11.1

  The yields of hydroxy nitrates from the reaction of selected C(2)-C(6) alkenes with OH in the presence of NO were measured at 296 +/- 3 K in a 9600 L photochemical smog chamber. Hydroxyl radicals were produced from the photolysis of isopropyl nitrite in the presence of NO. The loss of the alkene was followed using gas chromatography. The hydroxy nitrate products were determined using a combination of capillary chromatography and an organic nitrate specific chemiluminescence detector. The yield of hydroxy nitrates was observed to increase with the size of the precursor alkene as follows: ethene (0.86%), propene (1.5%), 1-butene (2.5%), cis-2-butene (3.4%), and 1-hexene (5.5%). Previous studies involving the production of alkyl nitrates from alkanes show a similar trend, but the yields reported here are a factor of 2-3 lower than for the corresponding simple alkylperoxy radical. The impact of a beta-hydroxy group on the nitrate yield is examined using an ab initio molecular orbital study. It indicates that a hydrogen-bonded peroxy nitrite intermediate is formed, which results in a decrease in D(0)(O-O) for the peroxy linkage of about 8 kJ/mol. This would be expected to effectively decrease the organic nitrate yield. The implications of these findings for the organic nitrate path as an atmospheric NO(x) removal mechanism are discussed.
• Ceric ammonium nitrate: A mild and efficient reagent for conversion of epoxides to β-nitrato alcohols
  作者：Nasser Iranpoor、Peyman Salehi

  DOI：10.1016/0040-4020(94)00979-5

  日期：1995.1

  Catalytic amount of Ce(IV) as ceric ammonium nitrate (CAN) alone or in the presence of excess nitrate ion reacts smoothly and efficiently with epoxides under mild conditions to produce the corresponding β-nitrato alcohols in good to excellent yields.

  单独或在过量硝酸根离子存在下，催化量的Ce（IV）以硝酸铈铵（CAN）的形式在温和条件下能与环氧化物平稳有效地反应，从而以良好或优异的收率生产相应的β-硝基醇。