N-Methyl-N,N-dioctyloctan-1-aminium nitrite | 96323-56-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-Methyl-N,N-dioctyloctan-1-aminium nitrite
• 英文别名: methyl(trioctyl)azanium;nitrite
• CAS: 96323-56-7
• 化学式: C₂₅H₅₄N*NO₂
• 分子量: 414.716
• InChiKey: ITZPMRKGPCVYKI-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  8.77
• 重原子数：
  29
• 可旋转键数：
  21
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  52.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-Methyl-N,N-dioctyloctan-1-aminium nitrite 、 在 二氧化氮 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 CoNO₆₃P₂W₁₇^(8-)*8C₂₅H₅₄N⁽¹⁺⁾
  参考文献：
  名称：

  Aerobic Carbon–Carbon Bond Cleavage of Alkenes to Aldehydes Catalyzed by First-Row Transition-Metal-Substituted Polyoxometalates in the Presence of Nitrogen Dioxide

  摘要：

  A new aerobic carbon carbon-bond cleavage reaction of linear di-substituted alkenes, to yield the corresponding aldehydes/ketones in high selectivity under mild reaction conditions, is described using copper(II)substituted polyoxometalates, such as {alpha(2)-Cu(L)P2W17O61}(8-) or {[(Cu-(L)](2)WZn(ZnW9O34)(2)}(12-), as catalysts, where L = NO2. A biorenewable-based substrate, methyl oleate, gave methyl 8-formyloctanoate and nonanal in >90% yield. Interestingly, cylcoalkenes yield the corresponding epoxides as products. These catalysts either can be prepared by pretreatment of the aqua-coordinated polyoxometalates (L = H2O) with NO2 or are formed in situ when the reactions are carried with nitroalkanes (for example, nitroethane) as solvents or cosolvents. Nitroethane was shown to release NO2 under reaction conditions. P-31 NMR shows that the Cu-NO2-substituted polyoxometalates act as oxygen donors to the C-C double bond, yielding a Cu-NO product that is reoxidized to Cu-NO2 under reaction conditions to complete a catalytic cycle. Stoichiometric reactions and kinetic measurements using {alpha(2)-Co(NO2)P2W17O61}(8-) as oxidant and trans-stilbene derivatives as substrates point toward a reaction mechanism for C-C bond cleavage involving two molecules of {alpha(2)-Co(NO2)P2W17O61}(8-) and one molecule of trans-stilbene that is sufficiently stable at room temperature to be observed by P-31 NMR.

  DOI：

  10.1021/ja502846h

文献信息

• Aerobic Carbon–Carbon Bond Cleavage of Alkenes to Aldehydes Catalyzed by First-Row Transition-Metal-Substituted Polyoxometalates in the Presence of Nitrogen Dioxide
  作者：Amir Rubinstein、Pablo Jiménez-Lozanao、Jorge J. Carbó、Josep M. Poblet、Ronny Neumann

  DOI：10.1021/ja502846h

  日期：2014.8.6

  A new aerobic carbon carbon-bond cleavage reaction of linear di-substituted alkenes, to yield the corresponding aldehydes/ketones in high selectivity under mild reaction conditions, is described using copper(II)substituted polyoxometalates, such as alpha(2)-Cu(L)P2W17O61}(8-) or [(Cu-(L)](2)WZn(ZnW9O34)(2)}(12-), as catalysts, where L = NO2. A biorenewable-based substrate, methyl oleate, gave methyl 8-formyloctanoate and nonanal in >90% yield. Interestingly, cylcoalkenes yield the corresponding epoxides as products. These catalysts either can be prepared by pretreatment of the aqua-coordinated polyoxometalates (L = H2O) with NO2 or are formed in situ when the reactions are carried with nitroalkanes (for example, nitroethane) as solvents or cosolvents. Nitroethane was shown to release NO2 under reaction conditions. P-31 NMR shows that the Cu-NO2-substituted polyoxometalates act as oxygen donors to the C-C double bond, yielding a Cu-NO product that is reoxidized to Cu-NO2 under reaction conditions to complete a catalytic cycle. Stoichiometric reactions and kinetic measurements using alpha(2)-Co(NO2)P2W17O61}(8-) as oxidant and trans-stilbene derivatives as substrates point toward a reaction mechanism for C-C bond cleavage involving two molecules of alpha(2)-Co(NO2)P2W17O61}(8-) and one molecule of trans-stilbene that is sufficiently stable at room temperature to be observed by P-31 NMR.