(1RS,3RS)-2-methyl-1-(1-naphthyl)-3-phenyl-2,3-dihydro-1H-naphtho[1,2-c][1,2]azaphosphole 1-oxide

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1RS,3RS)-2-methyl-1-(1-naphthyl)-3-phenyl-2,3-dihydro-1H-naphtho[1,2-c][1,2]azaphosphole 1-oxide
• 英文别名: (1R,3R)-2-methyl-1-naphthalen-1-yl-3-phenyl-3H-benzo[g][2,1]benzazaphosphole 1-oxide
• 化学式: C₂₈H₂₂NOP
• 分子量: 419.463
• InChiKey: SIICSYDNUSSFSN-DLFZDVPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  31
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  trimethoxonium tetrafluoroborate 、 N-benzyl-N-methyl-P,P-di-1-naphthylphosphinamide 在 仲丁基锂 作用下， 以 四氢呋喃 、 环己烷 为溶剂， 反应 14.5h， 生成 (1RS,3RS)-2-methyl-1-(1-naphthyl)-3-phenyl-2,3-dihydro-1H-naphtho[1,2-c][1,2]azaphosphole 1-oxide 、 (1RS,3RS,3aRS,9bSR)-2,9b-dimethyl-1-(1-naphthyl)-3-phenyl-2,3,3a,9b-tetrahydro-1H-naphtho[1,2-c][1,2]azaphosphole 1-oxide 、 (1RS,3SR,3aRS,9bRS)-2,9b-dimethyl-1-(1-naphthyl)-3-phenyl-2,3,3a,9b-tetrahydro-1H-naphtho[1,2-c][1,2]azaphosphole 1-oxide 、 (1RS,3RS,3aRS,9bRS)-2,9b-dimethyl-1-(1-naphthyl)-3-phenyl-2,3,3a,9b-tetrahydro-1H-naphtho[1,2-c][1,2]azaphosphole 1-oxide
  参考文献：
  名称：

  Dearomatizing Anionic Cyclization of N-Alkyl-N-benzyl(dinaphthyl)phosphinamides. A Facile Route to γ-(Amino)dihydronaphthalenylphosphinic Acids

  摘要：

  [GRAPHICS]The dearomatizing anionic cyclization of N-alkyl-N-benzyldi(n-naphthyl)phosphinamides (n = 1, 2) and subsequent trapping with a series of electrophiles (MeOH, Mel, CF3SO3Me, Me3O+BF4-, AllylBr, and PhCH2Br) have been accomplished. Optimized reaction conditions (base, temperature, reaction time) allow for synthesizing tetrahydro-1H-naphtho[1,2-c][1,21-azaphosphole 1-oxides 13 and 18 and tetrahydro-1H-naphtho[2,1-c][1,2]azaphosphole 3-oxides 16 and 27-29 in high yield and diastereoselectivity. Appropriate selection of the base proved to be critical for promoting anionic cyclization of 2-naphthyl derivatives. The dearomatized heterocycles are transformed quantitatively into gamma-(N-alkylamino)phosphinic acids by acid hydrolysis of the P-N linkage. Bioactivity assays on five human tumor cell lines for one of these amino acids revealed growth inhibition factors (GI(50)) at a micromolar scale. Additionally, evidence for the feasibility of intermolecular nucleophilic dearomatization and sequential nucleophilic attack to both aromatic rings of dinaphthylphosphinamides have been obtained.

  DOI：

  10.1021/jo701607s

文献信息

• Dearomatizing Anionic Cyclization of <i>N</i>-Alkyl-<i>N</i>-benzyl(dinaphthyl)phosphinamides. A Facile Route to γ-(Amino)dihydronaphthalenylphosphinic Acids
  作者：Gloria Ruiz-Gómez、María José Iglesias、Manuel Serrano-Ruiz、Fernando López-Ortiz

  DOI：10.1021/jo701607s

  日期：2007.12.1

  [GRAPHICS]The dearomatizing anionic cyclization of N-alkyl-N-benzyldi(n-naphthyl)phosphinamides (n = 1, 2) and subsequent trapping with a series of electrophiles (MeOH, Mel, CF3SO3Me, Me3O+BF4-, AllylBr, and PhCH2Br) have been accomplished. Optimized reaction conditions (base, temperature, reaction time) allow for synthesizing tetrahydro-1H-naphtho[1,2-c][1,21-azaphosphole 1-oxides 13 and 18 and tetrahydro-1H-naphtho[2,1-c][1,2]azaphosphole 3-oxides 16 and 27-29 in high yield and diastereoselectivity. Appropriate selection of the base proved to be critical for promoting anionic cyclization of 2-naphthyl derivatives. The dearomatized heterocycles are transformed quantitatively into gamma-(N-alkylamino)phosphinic acids by acid hydrolysis of the P-N linkage. Bioactivity assays on five human tumor cell lines for one of these amino acids revealed growth inhibition factors (GI(50)) at a micromolar scale. Additionally, evidence for the feasibility of intermolecular nucleophilic dearomatization and sequential nucleophilic attack to both aromatic rings of dinaphthylphosphinamides have been obtained.