N-Benzyliden-α-acetoxy-benzylamin | 14151-94-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-Benzyliden-α-acetoxy-benzylamin
• CAS: 14151-94-1
• 化学式: C₁₆H₁₅NO₂
• 分子量: 253.301
• InChiKey: WYBOUIXIIBDUSM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.37
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  38.66
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  乙酸盐 、 1,3-diphenylazaallenium cation 以 水 、 乙腈 为溶剂， 生成 N-Benzyliden-α-acetoxy-benzylamin
  参考文献：
  名称：

  [3 + 2] Cycloadditions and Protonation by Alcohols of Photochemically Generated Nitrile Ylides from 2H-Azirines. Formation and Reactivities of Azaallenium Cations

  摘要：

  On photolysis of 2H-phenylazirines id acetonitrile or alcohol solution with 248 nm laser light, phenylnitrile ylides are formed by heterolytic cleavage of the C-C bond of the azirines. The absorption spectra of the ylides are characterized by two strong bands, at ca. 240 and 280 nm, and a weak band, at 380 nm. Electron-deficient olefins react with the nitrile ylides by 1,3-dipolar cycloaddition to yield 5-membered N-heterocycles (rate constants between 4 x 10(5) and 7 x 10(9) M-1 s(-1), the Hammett-p value for the para-substituent on the phenyl ring is -0.9). In alcohols as solvents, the nitrile ylides are protonated to yield azaallenium cations, whose spectroscopic properties and reactivities with nucleophiles are described. The protonation rates of the ylides in alcohols increase with the acidity of the alcohol. On the basis of the large kinetic isotope effect for protonation of ylide by alcohol (k(H)/k(D) = 5.5), the transition state for the ylide protonation is concluded to be linear.

  DOI：

  10.1021/ja971648n

文献信息

• The reaction of lead tetraacetate with primary and secondary amines containing an α-methylene group
  作者：A. Stojiljković、V. Andrejević、M.Lj. Mihailovi

  DOI：10.1016/0040-4020(67)85017-8

  日期：1967.1

  Primary alkyl- and arylalkyl-amines containing a methylene group in the α-position were dehydrogenated by means of lead tetraacetate to give the corresponding cyanides in yields ranging up to 60%. By-products of this reaction are N-alkylacetamides, N-alkylamides of the corresponding alkanoic acids and other acetoxylated derivatives.

  用四乙酸铅将在α位上含有亚甲基的伯烷基-和芳基烷基-胺脱氢，得到相应的氰化物，产率高达60％。该反应的副产物是N-烷基乙酰胺，相应链烷酸的N-烷基酰胺和其他乙酰氧基化衍生物。