N-(5-hexenyl)-N-methylhydroxylamine | 35365-16-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(5-hexenyl)-N-methylhydroxylamine
• 英文别名: N-Methyl-N-(5-hexenyl)hydroxylamine；N-hex-5-enyl-N-methyl-hydroxylamine；N-Methyl-N-hexen-(5)-yl-(1)-hydroxylamin；N-Methyl-N-hexen-(5)-yl-hydroxylamin；5-Hexenyl-N-methyl-hydroxylamin；N-hex-5-enyl-N-methylhydroxylamine
• CAS: 35365-16-3
• 化学式: C₇H₁₅NO
• 分子量: 129.202
• InChiKey: BMZWFWIJJRXTJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  9
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(5-hexenyl)-N-methylhydroxylamine 在 溶剂黄146 、 mercury(II) oxide 、 锌 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 cis-N-methyl-2-hydroxymethylcyclopentylamine
  参考文献：
  名称：

  The Addition of Nitrones to Olefins. Fused Bicyclic Isoxazolidines

  摘要：

  DOI：

  10.1021/ja01072a031
• 作为产物：
  描述：

  N-methylazacycloheptane N-oxide 生成 N-(5-hexenyl)-N-methylhydroxylamine
  参考文献：
  名称：

  CIGANEK, ENGELBERT, J. ORG. CHEM., 55,(1990) N0, C. 3007-3009

  摘要：

  DOI：

文献信息

• Configurational and conformational analysis of cyclic amine oxides
  作者：Y. Shvo、E.D. Kaufman

  DOI：10.1016/0040-4020(72)84021-3

  日期：1972.1

  and their configurations assigned. It has been established that the equatorial N-methyl in a piperidine oxide system gives rise to an NMR signal at lower magnetic field than the axial one. The conformational equilibrium of N-methylpiperidine oxide was investigated. The equilibrium constant and the conformational free energy were evaluated.

  通过氧化4-叔丁基-N-甲基哌啶来制备两种立体异构的4-叔丁基-N-甲基哌啶-N-氧化物。它们被分离，表征并分配了它们的配置。已经确定，哌啶氧化物系统中的赤道N-甲基在比轴向磁场低的磁场下产生NMR信号。研究了N-甲基哌啶氧化物的构象平衡。评价了平衡常数和构象自由能。
• Reverse Cope elimination reactions. 1. Mechanism and scope
  作者：Engelbert Ciganek、John M. Read、Joseph C. Calabrese

  DOI：10.1021/jo00123a013

  日期：1995.9

  N-4-Pentenyl- and N-5-hexenyl-N-methylhydroxylamine cyclized under mild conditions in a reverse Cope elimination reaction to give 1,2-dimethylpyrrolidine N-oxide and 1,2-dimethylpiperidine N-oxide, respectively. The reaction was shown to be concerted and thermodynamically controlled. The scope of this novel cyclization is discussed, and comparisons are made with the closely related and previously reported cyclization of monosubstituted alkenylhydroxylamines to give cyclic hydroxylamines.
• Amine Oxides. VII. The Thermal Decomposition of the N-Oxides of N-Methylazacycloalkanes^1,2
  作者：Arthur C. Cope、Norman A. LeBel

  DOI：10.1021/ja01502a052

  日期：1960.9

  Ring cleavage of the N-oxides of N-methylazacycloalkanes by a thermal elimination reaction does not occur when the ring is six-membered and becontes progressively easier as the ring size is increased from seven to eight atoms. N-Methylpiperidine oxide gave no product from a cis beta-elimination reaction, while pyrolysis of the homologous N-methylhexamethyleneimine and N-methylheptamethyleneimine oxides led to the unsaturated hydroxylamines in yields of 53 and 79%, respectively. These results support a planar five-membered transition state for the amine oxide pyrolysis. The unsaturated hydroxylamines were converted to unsaturated and saturated secondary amines. The thermal decomposition of a mixture of he cis and trans isomers of N-methyl-alpha-pipecoline oxide formed the expected N-methyl-N-5-hexenylhydroxylamine as well as a saturated bicyclic product, formulated as cis-N-methyl-3-oxa-2-azabicyclo [3.3.01 octane. A possible mechanism for the formation of this product is presented. The cis and trans isomers of N-methyl-a-pipecoline oxide have been separated and characterized. Each Of the isomers has been pyrolyzed separately and only trans-N-methyl-a-pipecoline oxide formed the expected unsaturated hydroxylamine.
• Reverse Cope eliminations. Pyrrolidine and piperidine N-oxides by intramolecular addition of N,N-disubstituted hydroxylamines to unactivated double bonds
  作者：Engelbert Ciganek

  DOI：10.1021/jo00297a011

  日期：1990.5
• THE ADDITION OF NITRONES TO OLEFINS. A NEW ROUTE TO ISOXAZOLIDINES
  作者：Norman A. LeBel、Jong Jai Whang

  DOI：10.1021/ja01532a061

  日期：1959.12