2-octyl nitrate | 7214-64-4

• 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: 2-octyl nitrate
• 英文别名: 2-Octylnitrat；octan-2-yl nitrate
• CAS: 7214-64-4
• 化学式: C₈H₁₇NO₃
• 分子量: 175.228
• InChiKey: QCOKASLKYUXYJH-UHFFFAOYSA-N

物化性质

• 保留指数：
  1150;1150

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-octyl nitrate 、 4-甲基环己酮 生成 (+/-)-4-methyl-2-nitro-cyclohexanone; potassium-salt
  参考文献：
  名称：

  Asymmetric Syntheses. II. The Action of Optically Active Nitrates on Cyclic Ketones

  摘要：

  DOI：

  10.1021/ja01329a050
• 作为产物：
  描述：

  正辛烷 在 硝酸 、 五氧化二氮 作用下， 生成 2-octyl nitrate
  参考文献：
  名称：

  Oxidation of n-Octane with White Fuming Nitric Acid¹

  摘要：

  DOI：

  10.1021/jo01097a023

文献信息

• Mercury-assisted solvolyses of alkyl halides
  作者：A. McKillop、M.E. Ford

  DOI：10.1016/s0040-4020(01)97118-2

  日期：1974.1

  wide variety of alkyl halides with mercury(I) and/or (II) nitrate in 1,2-dimethoxyethane, mercury(II) acetate in acetic acid, aqueous mercury(II) perchlorate, and mercury(II) perchlorate in alcohol solvents have been investigated; as a result, simple high yield procedures for the conversion of alkyl halides into the corresponding nitrate esters, acetate esters, alcohols and ethers have been developed.

  各种烷基卤与1,2-二甲氧基乙烷中的硝酸汞（I）和/或硝酸盐（II），乙酸中的乙酸汞（II）在乙酸中，高氯酸汞（II）和高氯酸汞（II）的反应在酒精溶剂中已被研究；结果，已经开发了用于将烷基卤化物转化为相应的硝酸酯，乙酸酯，醇和醚的简单的高收率方法。
• Electroorganic Chemistry; 145:¹Coupling Reaction of an Olefin with a Radical NO₃ ^·Generated by Anodic Oxidation of NO₃ ^-
  作者：Tatsuya Shono、Mayuree Chuankamnerdkarn、Hirofumi Maekawa、Manabu Ishifune、Shigenori Kashimura

  DOI：10.1055/s-1994-25594

  日期：——

  When NO- 3 is electrochemically oxidized in the presence of a variety of terminal and 1,2-disubstituted olefins 1 in a mixed solvent system (MeCN: H2O: Et2O = 10: 2:1), a radical NO3 is generated from NO- 3 and nitrate esters 3 are formed by a new coupling reaction of the olefin with the radical. The products 3 can be further transformed into the corresponding alcohols 4 and alkyl iodides 5. Under the same reaction conditions, 1,1-di- and 1,1,2-trisubstituted olefins 6 do not give nitrate esters but afford oxazoline derivatives 7. (1S,5S)-(-)-ß-Pinene (13) is diastereoselectively transformed into (1S,2R,5S)-(-)-myrtanol (14) by this technique.

  当在混合溶剂系统（MeCN:H2O:Et2O = 10:2:1）中，NO-3在存在多种末端和1,2-二取代烯烃1的情况下进行电化学氧化时，NO-3会生成自由基NO3，并且通过烯烃与该自由基的新偶联反应形成硝酸酯3。产物3可以进一步转化为相应的醇4和烷基碘5。在相同的反应条件下，1,1-二取代和1,1,2-三取代烯烃6不产生硝酸酯，而是生成恶唑啉衍生物7。通过这种技术，(1S,5S)-(-)-β-蒎烯（13）可以立体选择性地转化为(1S,2R,5S)-(-)-杨梅醇（14）。
• Inversion of configuration of alcohols through nucleophilic displacement promoted by nitrate ions.
  作者：Gianfranco Cainelli、Francesco Manescalchi、Giorgio Martelli、Mauro Panunzio、Laura Plessi

  DOI：10.1016/s0040-4039(00)98300-x

  日期：1985.1

  Inversion of configuration of hydroxy functionalities in biologically significant structures has been performed under mild conditions through nucleophilic displacement by nitrate ion.

  在温和的条件下，通过硝酸根离子的亲核取代，已经完成了生物学上重要结构中羟基官能团构型的转化。
• Convenient Preparation of Alkyl Nitrates Free of Nitrites with Potassium Nitrate and Boron Trifluoride Hydrate
  作者：George A. Olah、Qi Wang、Xing-ya Li、G. K. Surya Prakash

  DOI：10.1055/s-1993-25830

  日期：——

  Primary and secondary alkyl nitrates free of nitrites were conveniently prepared by treating the corresponding alcohols with potassium nitrate and boron trifluoride 1.25 hydrate. This procedure was also successful for the preparation of 1-adamantyl nitrate.

  不含亚硝酸盐的一级和二级烷基硝酸酯可通过方便地将相应醇与硝酸钾和氟硼酸钾水合物（1.25水合物）反应来制备。此方法同样成功用于制备硝酸金刚烷。
• Preparation of Alkyl Nitrates, Nitrites, and Thiocyanates from Alcohols Utilizing Trichloroisocyanuric Acid with Triphenylphosphine
  作者：Gene A. Hiegel、Jeremiah Nguyen、Yan Zhou

  DOI：10.1081/scc-200025580

  日期：2004.1.1

  Abstract Alcohols in acetonitrile are converted into alkyl nitrates, nitrites, or thiocyanates by the action of triphenylphosphine and trichloroisocyanuric acid along with silver nitrate, silver nitrite, or sodium thiocyanate, respectively.

  摘要 乙腈中的醇在三苯基膦和三氯异氰尿酸与硝酸银、亚硝酸银或硫氰酸钠的作用下分别转化为硝酸烷基酯、亚硝酸盐或硫氰酸盐。