1-(重氮甲基)-8-甲基萘 | 70840-50-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1-(重氮甲基)-8-甲基萘
• 英文名称: 1-(diazomethyl)-8-methylnaphthalene
• 英文别名: (8-methyl-1-naphthyl)diazomethane
• CAS: 70840-50-5
• 化学式: C₁₂H₁₀N₂
• 分子量: 182.225
• InChiKey: GOOAZGYPBYKQQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(重氮甲基)-8-甲基萘 以 乙醚 、 2-甲基丁烷 为溶剂， 以100%的产率得到1.8-Dimethylen-1.8-dihydro-naphtalin
  参考文献：
  名称：

  A carbene to biradical rearrangement: reaction paths from (8-methyl-1-naphthyl)carbene to acenaphthene

  摘要：

  Photochemical nitrogen elimination from 1-(diazomethyl)-8-methylnaphthalene (2) yields acenaphthene (3) via the reactive intermediates (8-methyl-1-naphthyl)carbene (a) and 1,8-naphthoquinodimethane (b). The triplet biradical b was observed by absorption spectroscopy at 77 K and by laser flash photolysis at room temperature. The cyclization of triplet b to triplet 3 is forbidden by state symmetry. Two pathways for the reaction b --> 3 have been identified: (1) intersystem crossing to the singlet groud state is rate-determining in the thermal decay of b, and (2) an adiabatic reaction yielding 3 in the lowest excited triplet state was observed upon photolysis of triplet b at 77 K. The carbene precursor of b was intercepted by methanol. This resulted in a reduced yield of transient b in acetonitrile. The trapping reaction did not obey a linear Stern-Volmer relationship.

  DOI：

  10.1021/ja00021a037
• 作为产物：
  描述：

  8-甲基-1-萘甲醛 在 氢氧化钾 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.17h， 生成 1-(重氮甲基)-8-甲基萘
  参考文献：
  名称：

  1-Naphthylcarbene: spectroscopy, kinetics, and mechanisms

  摘要：

  DOI：

  10.1021/ja00274a013

文献信息

• The mechanism of intersystem crossing and ring closure of the triplet 1,8-naphthoquinodimethane biradical
  作者：Matthew S. Platz

  DOI：10.1021/ja00523a061

  日期：1980.1