2-methyleneaminonaphthalene | 2955-17-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-methyleneaminonaphthalene
• 英文别名: methylene-[2]naphthyl-amine；Methylen-β-naphthylamin；Methylen-[2]naphthyl-amin；N-(Naphthalen-2-Yl)methanimine；N-naphthalen-2-ylmethanimine
• CAS: 2955-17-1
• 化学式: C₁₁H₉N
• 分子量: 155.199
• InChiKey: FGRABSHVUNBHIE-UHFFFAOYSA-N

物化性质

• 熔点：
  184 °C (decomp)
• 沸点：
  296.2±23.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-methyleneaminonaphthalene 、 2,2-二甲基-4,6-二氧环己烷-1-羧酸甲酯 以 乙醇 为溶剂， 以2.5 g的产率得到methyl 9,9-dimethyl-11-oxo-8,9,10,12-tetrahydro-7H-benzo[a]acridine-10-carboxylate
  参考文献：
  名称：

  Condensation of 2-naphthylamine or N-benzyl-2-naphthylamines with formaldehyde and methyl 2,2-dimethyl-4,6-dioxocyclohexane-3-carboxylate

  摘要：

  Condensation of 2-naphthylamine with formaldehyde and methyl 2,2-dimethyl-4,6-dioxocyclohexanecarboxylate afforded depending on the reaction conditions methyl 9,9-dimethyl-11-oxo-8,9,10,12-tetrahydro-7H-benzo[a]acridine-10-carboxylate or 4-alkoxymethyl-1,4-dihydro-2',6'-dioxo-4',4'-dimethyl-2'H,3H,6'Hspirobenzo[f]quinoline-2,1'-cyclohexyl-3'-carboxylate. The condensation of N-benzyl-2-naphthylamines with formaldehyde and methyl 2,2-dimethyl-4,6-dioxocyclohexanecarboxylate provided with the quantitative yield the corresponding methyl 4-benzyl-1,4-dihydro-2',6'-dioxo-4',4'-dimethyl-2'H,3H,6'H-spirobenzo[f]quinoline-2,1'-cyclohexyl-3'-carboxylates.

  DOI：

  10.1134/s1070428012110085
• 作为产物：
  描述：

  聚合甲醛 、 2-萘胺 在 溶剂黄146 作用下， 生成 2-methyleneaminonaphthalene
  参考文献：
  名称：

  Moehlau; Haase, Chemische Berichte, 1902, vol. 35, p. 4164

  摘要：

  DOI：

文献信息

• One-stage synthesis of benzoacridine and benzophenanthroline functionalized derivatives
  作者：A. P. Kadutskii、N. G. Kozlov

  DOI：10.1134/s1070428006050174

  日期：2006.5

  A one-stage procedure was developed for preparing new partially hydrogenated derivatives of benzoacridine and benzophenanthroline. The procedure was a triple condensation of 6-aminoquinoline or 2-naphthylamine with formaldehyde and hydroxycyclohexylidenepropanedinitriles, functionalized analogs of cyclic beta-diketones.
• Morgan, Journal of the Chemical Society, 1898, vol. 73, p. 546,547, 549
  作者：Morgan

  DOI：——

  日期：——
• Moehlau; Haase, Chemische Berichte, 1902, vol. 35, p. 4164
  作者：Moehlau、Haase

  DOI：——

  日期：——
• ——
  作者：N. G. Kozlov、A. P. Kadutskii

  DOI：10.1023/a:1015375313521

  日期：——

  2-Methyleneaminonaphthalene smoothly reacts with cyclic beta-diketones to afford azaphenanthrene derivatives in high yield. The dihydropyridine ring in the products can be oxidized to pyridine ring. The oxidation products, unlike their precursors and analogs having an aryl substituent in the a-position with respect to the nitrogen atom, react with hydroxylamine at the carbonyl group to give the corresponding oximes and in some cases undergo Knoevenagel condensation with malononitrile. Hydrolysis of the condensation product yields the respective diamide.
• Condensation of 2-naphthylamine or N-benzyl-2-naphthylamines with formaldehyde and methyl 2,2-dimethyl-4,6-dioxocyclohexane-3-carboxylate
  作者：N. G. Kozlov、A. P. Kadutskii、A. V. Baranovskii

  DOI：10.1134/s1070428012110085

  日期：2012.11

  Condensation of 2-naphthylamine with formaldehyde and methyl 2,2-dimethyl-4,6-dioxocyclohexanecarboxylate afforded depending on the reaction conditions methyl 9,9-dimethyl-11-oxo-8,9,10,12-tetrahydro-7H-benzo[a]acridine-10-carboxylate or 4-alkoxymethyl-1,4-dihydro-2',6'-dioxo-4',4'-dimethyl-2'H,3H,6'Hspirobenzo[f]quinoline-2,1'-cyclohexyl-3'-carboxylate. The condensation of N-benzyl-2-naphthylamines with formaldehyde and methyl 2,2-dimethyl-4,6-dioxocyclohexanecarboxylate provided with the quantitative yield the corresponding methyl 4-benzyl-1,4-dihydro-2',6'-dioxo-4',4'-dimethyl-2'H,3H,6'H-spirobenzo[f]quinoline-2,1'-cyclohexyl-3'-carboxylates.