2-硝基-2-己烯 | 6065-17-4

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 中文名称: 2-硝基-2-己烯
• 英文名称: 2-nitrohex-2-ene
• 英文别名: 2-Nitro-hex-2-en；2-Nitro-hex-2-ene
• CAS: 6065-17-4
• 化学式: C₆H₁₁NO₂
• 分子量: 129.159
• InChiKey: IPHWNDSKYDRUFO-UHFFFAOYSA-N

物化性质

• 沸点：
  209.22°C (rough estimate)
• 密度：
  1.0359 (estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2904209090

反应信息

• 作为反应物：
  描述：

  2-硝基-2-己烯 在 sodium hydroxide 、 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 2-nitrohexane
  参考文献：
  名称：

  Reduction of nitroalkenes to nitroalkanes with aqueous sodium borohydride

  摘要：

  DOI：

  10.1021/jo01287a116
• 作为产物：
  描述：

  3-acetoxy-2-nitro-hexane 在 碳酸氢钠 、 苯 作用下， 生成 2-硝基-2-己烯
  参考文献：
  名称：

  Reactions of Diazo Compounds with Nitroölefins. I. The Preparation of Pyrazoles

  摘要：

  DOI：

  10.1021/ja01165a003

文献信息

• Palladium catalyzed synthesis of tertiary allylamines. Utilization of α-nitro olefins as allylic nitro compounds
  作者：Rui Tamura、Koji Hayashi、Yoshiki Kai、Daihei Oda

  DOI：10.1016/s0040-4039(01)81459-3

  日期：1984.1

  Reaction of α-nitro olefins with secondary amines in the presence of palladium(O) catalyst affords allylic amines.

  在钯（O）催化剂存在下，α-硝基烯烃与仲胺的反应得到烯丙基胺。
• Preparation of polyfunctional nitro olefins and nitroalkanes using the copper-zinc reagents RCu(CN)ZnI
  作者：Carole Jubert、Paul Knochel

  DOI：10.1021/jo00046a027

  日期：1992.9

  The addition of the copper-zinc reagents RCu(CN)ZnX to a variety of nitro olefins produces polyfunctional nitroalkanes in high yields. The intermediate zinc or copper nitronates can be directly submitted to a Nef reaction (O3,-78-degrees-C) and converted to polyfunctional ketones in a one-pot procedure. The addition of RCu(CN)ZnX to nitro olefins bearing a leaving group (RSO2, RS) in the beta-position provides pure (E)-nitro olefins in excellent yields. The reaction has been applied for the stereoselective preparation of 1,3-nitrodienes and for a Diels-Alder reaction precursor.
• Nasakin, O. E.; Lukin, P. M.; Zil'berg, S. P., Journal of Organic Chemistry USSR (English Translation), 1988, vol. 24, p. 901 - 908
  作者：Nasakin, O. E.、Lukin, P. M.、Zil'berg, S. P.、Terent'ev, P. B.、Bulai, A. Kh.、et al.

  DOI：——

  日期：——
• Electrochemical Reductive Coupling Reactions of Aliphatic Nitroalkenes.
  作者：Peter Mikesell、Michael Schwaebe、Marcello DiMare、R. Daniel Little、Giuseppe Silvestri、André Tallec、Tatsuya Shono、H. Toftlund

  DOI：10.3891/acta.chem.scand.53-0792

  日期：——

  We describe how to selectively affect either beta-to-beta coupling (electrohydro-dimerization) or coupling between the alpha and beta centers of aliphatic nitroalkenes, the latter in a catalytic process that can be initiated both with and without electrochemistry. Of particular significance is our discovery of conditions that allow electrohydrodimerization to be conducted using aliphatic nitroalkenes bearing acidic protons. Thus, one can affect at will, either a catalytic alpha-to-beta coupling or an electrohydrodimerization using substrates that bear acidic protons, as well as those that do not. We also describe both voltammetric and ESR studies of the simple 1 -nitro-3,3-dimethyl-1-butene, as well as the results of quantum mechanical calculations that shed light upon the nature of radial anions derived from electron deficient olefins. Both calculation and experiment suggest: that the reluctance of these materials to undergo electrohydrodimerization can be correlated with the low electron density on carbon and the corresponding high value on oxygen, of the radical anion.
• Nightingale; Janes, Journal of the American Chemical Society, 1944, vol. 66, p. 353
  作者：Nightingale、Janes

  DOI：——

  日期：——