trans-1-(o-azidophenyl)-1-pentene

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: trans-1-(o-azidophenyl)-1-pentene
• 英文别名: (E)-1-o-Azidophenyl-1-penten；1-azido-2-[(E)-pent-1-enyl]benzene
• 化学式: C₁₁H₁₃N₃
• 分子量: 187.244
• InChiKey: VLHUHHUARVPAOU-QPJJXVBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  14.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  反-1,3-戊二烯 、 trans-1-(o-azidophenyl)-1-pentene 在 aluminum (III) chloride 作用下， 以 正己烷 为溶剂， 反应 4.0h， 生成 4-[(2E)-1-methylbut-2-en-1-yl]-phenyl azide
  参考文献：
  名称：

  Thermal Intramolecular Transformation of Key Intermediates in the Photooxidation of para-Allyl-Substituted Phenyl Azide

  摘要：

  The electronic spectra, kinetic regularities, and the mechanism of decay of the cis and trans isomeric forms of 4-[(2E)-1-methylbut-2-en-1-yl]phenylnitroso oxide (2) were studied by flash photolysis and product analysis. The mechanism of the consumption of this nitroso oxide is the same as the one proposed earlier for 4-methoxyphenylnitroso oxide. The trans-2 isomer is converted into cis-2, which undergoes cyclization to the substituted benzo[d][1,2,3]clioxazole 3. The reopening of the dioxazole ring yields nitrile oxide 4. The final product (3,4-dimethyl-3a,4-dihydro-2,1-benzisoxazol-5(3H)-ylidene)acetaldehyde (5) is formed by the intramolecular [3 + 2] -cycloaddition of the nitrile oxide group of 4 to the allylic double bond. To support the proposed mechanism, the quantum chemical calculations have been employed.

  DOI：

  10.1021/jp401038g

文献信息

• Thermal Intramolecular Transformation of Key Intermediates in the Photooxidation of <i>para</i>-Allyl-Substituted Phenyl Azide
  作者：Ekaterina M. Chainikova、Evgeniy Yu. Pankratyev、Aigul N. Teregulova、Rail R. Gataullin、Rustam L. Safiullin

  DOI：10.1021/jp401038g

  日期：2013.4.4

  The electronic spectra, kinetic regularities, and the mechanism of decay of the cis and trans isomeric forms of 4-[(2E)-1-methylbut-2-en-1-yl]phenylnitroso oxide (2) were studied by flash photolysis and product analysis. The mechanism of the consumption of this nitroso oxide is the same as the one proposed earlier for 4-methoxyphenylnitroso oxide. The trans-2 isomer is converted into cis-2, which undergoes cyclization to the substituted benzo[d][1,2,3]clioxazole 3. The reopening of the dioxazole ring yields nitrile oxide 4. The final product (3,4-dimethyl-3a,4-dihydro-2,1-benzisoxazol-5(3H)-ylidene)acetaldehyde (5) is formed by the intramolecular [3 + 2] -cycloaddition of the nitrile oxide group of 4 to the allylic double bond. To support the proposed mechanism, the quantum chemical calculations have been employed.