3-Nitro-2-phenyl-1,2-dihydronaphthalene | 1450995-35-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-Nitro-2-phenyl-1,2-dihydronaphthalene
• 英文别名: 3-nitro-2-phenyl-1,2-dihydronaphthalene
• CAS: 1450995-35-3
• 化学式: C₁₆H₁₃NO₂
• 分子量: 251.285
• InChiKey: FTMGALCRQIPENG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-Nitro-2-phenyl-1,2-dihydronaphthalene 在 N-溴代丁二酰亚胺(NBS) 、 palladium 10% on activated carbon 、 氢气 、 过氧化苯甲酰 作用下， 以 二氯甲烷 、 乙酸乙酯 、 1,2-二氯乙烷 为溶剂， 反应 20.0h， 生成 2-氨基-3-苯基-萘
  参考文献：
  名称：

  Regiospecific Synthesis of Novel Cyclic Nitrostyrenes and 3-Substituted 2-Nitronaphthalenes

  摘要：

  A two-step, practical, regiospecific, and readily scalable benzannulation protocol for the preparation of novel 3-alkyl- and 3-aryl-substituted 2-nitronaphthalenes is disclosed. Addition of a beta-nitrostyrene or nitroalkene to a solution of freshly prepared lithiated o-tolualdehyde tert-butyl imine first leads to the formation of a nitronate, via rapid 1,4-addition, then an intramolecular aza-Henry reaction takes place to afford a six-membered carbocycle. Subsequent treatment of the reaction mixture with aqueous acid affords novel substituted cyclic nitrostyrenes that can be conveniently aromatized via a one-pot radical-induced bromination and elimination sequence to furnish the corresponding 3-alkyl- or 3-aryl-2-nitronaphthalenes in excellent yields. The straightforward syntheses of 2-aminonaphthalenes, substituted BINAMs, 2-naphthols as well as tricyclic fused 1,2,3-triazoles are also described.

  DOI：

  10.1055/s-0033-1338867
• 作为产物：
  描述：

  反式硝基苯乙烯 、 N-<(2-Methylphenyl)methylene>-1,1-dimethylethanamine 在 2,2,6,6-四甲基哌啶 、 正丁基锂 、 盐酸 、 水 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以76%的产率得到3-Nitro-2-phenyl-1,2-dihydronaphthalene
  参考文献：
  名称：

  Regiospecific Synthesis of Novel Cyclic Nitrostyrenes and 3-Substituted 2-Nitronaphthalenes

  摘要：

  A two-step, practical, regiospecific, and readily scalable benzannulation protocol for the preparation of novel 3-alkyl- and 3-aryl-substituted 2-nitronaphthalenes is disclosed. Addition of a beta-nitrostyrene or nitroalkene to a solution of freshly prepared lithiated o-tolualdehyde tert-butyl imine first leads to the formation of a nitronate, via rapid 1,4-addition, then an intramolecular aza-Henry reaction takes place to afford a six-membered carbocycle. Subsequent treatment of the reaction mixture with aqueous acid affords novel substituted cyclic nitrostyrenes that can be conveniently aromatized via a one-pot radical-induced bromination and elimination sequence to furnish the corresponding 3-alkyl- or 3-aryl-2-nitronaphthalenes in excellent yields. The straightforward syntheses of 2-aminonaphthalenes, substituted BINAMs, 2-naphthols as well as tricyclic fused 1,2,3-triazoles are also described.

  DOI：

  10.1055/s-0033-1338867

文献信息

• Regiospecific Synthesis of Novel Cyclic Nitrostyrenes and 3-Substituted 2-Nitronaphthalenes
  作者：László Kürti、Craig Keene

  DOI：10.1055/s-0033-1338867

  日期：——

  A two-step, practical, regiospecific, and readily scalable benzannulation protocol for the preparation of novel 3-alkyl- and 3-aryl-substituted 2-nitronaphthalenes is disclosed. Addition of a beta-nitrostyrene or nitroalkene to a solution of freshly prepared lithiated o-tolualdehyde tert-butyl imine first leads to the formation of a nitronate, via rapid 1,4-addition, then an intramolecular aza-Henry reaction takes place to afford a six-membered carbocycle. Subsequent treatment of the reaction mixture with aqueous acid affords novel substituted cyclic nitrostyrenes that can be conveniently aromatized via a one-pot radical-induced bromination and elimination sequence to furnish the corresponding 3-alkyl- or 3-aryl-2-nitronaphthalenes in excellent yields. The straightforward syntheses of 2-aminonaphthalenes, substituted BINAMs, 2-naphthols as well as tricyclic fused 1,2,3-triazoles are also described.