5-(4-Bromo-phenyl)-3-naphthalen-1-yl-4,5-dihydro-isoxazole | 142746-06-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-(4-Bromo-phenyl)-3-naphthalen-1-yl-4,5-dihydro-isoxazole
• 英文别名: 5-(4-Bromophenyl)-3-naphthalen-1-yl-4,5-dihydro-1,2-oxazole
• CAS: 142746-06-3
• 化学式: C₁₉H₁₄BrNO
• 分子量: 352.23
• InChiKey: KDBCWLRSZSYFIU-UHFFFAOYSA-N

物化性质

• 熔点：
  170 °C(Solv: ethanol (64-17-5); benzene (71-43-2))
• 沸点：
  482.2±55.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-(p-Bromocinnamoyl)naphthalene 在 吡啶 、 盐酸羟胺 作用下， 反应 0.07h， 以65%的产率得到5-(4-Bromo-phenyl)-3-naphthalen-1-yl-4,5-dihydro-isoxazole
  参考文献：
  名称：

  Sharma, Sharda; Pathak, Late V. N.; Madan, Harsha, Indian Journal of Heterocyclic Chemistry, 2010, vol. 19, # 4, p. 337 - 340

  摘要：

  DOI：

文献信息

• Insertion of nitrogen oxide and nitrosonium ion into the cyclopropane ring: a new route to 2-isoxazolines and its mechanistic studies
  作者：Kazuhiko Mizuno、Nobuyuki Ichinose、Toshiyuki Tamai、Yoshio Otsuji

  DOI：10.1021/jo00043a026

  日期：1992.8

  The 9,10-dicyanoanthracene (DCA)-sensitized photoreaction of 1,2-diarylcyclopropanes 1a-d in nitrogen oxide (NO)-saturated CH3CN afforded 3,5-diaryl-2-isoxazolines 2a-d in excellent yields. The reaction of 1a-d with NOBF4 or with a mixture of NO and O2 in CH3CN also afforded 2a-d or 2a-b. These reactions proceed via the attack of NO on the radical cation of 1, which is formed by electron transfer from 1 to 1DCA* or NO+. The reaction of 1-alkyl-2-arylcyclopropanes with NOBF4 afforded mixtures of 3-alkyl-5-aryl-2-isoxazolines and 4-alkyl-5-aryl-2-isoxazolines via the direct attack of NO+ on the cyclopropane rings. The reaction of 1,1,2,2-tetraphenylcyclopropane with NOBF4 afforded 2,3,5,5-tetraphenyl-2-isoxazolinium tetrafluoroborate via the migration of the phenyl group to nitrogen.