[2]naphthyl-piperonyl-amine | 97306-77-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: [2]naphthyl-piperonyl-amine
• 英文别名: [2]Naphthyl-piperonyl-amin；N-(1,3-benzodioxol-5-ylmethyl)naphthalen-2-amine
• CAS: 97306-77-9
• 化学式: C₁₈H₁₅NO₂
• 分子量: 277.323
• InChiKey: OHYSZQYLWPUKNW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [2]naphthyl-piperonyl-amine 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 二甲基亚砜 作用下， 反应 22.0h， 以88%的产率得到2-(benzo[d][1,3]dioxol-5-yl)naphtho[2,1-d]thiazole
  参考文献：
  名称：

  通过CH键功能化形成双CS键：由N-取代的芳基胺和元素硫合成苯并噻唑和萘并[2,1-d]噻唑

  摘要：

  在无金属条件下开发了一种新颖，原子经济，环保的方法，该方法可从N-取代的芳基胺和元素硫合成2-取代的苯并噻唑和2-取代的萘并[2,1-d]噻唑。该反应经历了通过CH键官能化形成双CS键的过程。

  DOI：

  10.1039/c7cc07366f
• 作为产物：
  描述：

  piperonal-[2]naphthylimine 在 sodium tetrahydroborate 、 溶剂黄146 作用下， 以 苯 为溶剂， 以42%的产率得到[2]naphthyl-piperonyl-amine
  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

文献信息

• Ciusa; Zerbini, Gazzetta Chimica Italiana, 1920, vol. 50 II, p. 325
  作者：Ciusa、Zerbini

  DOI：——

  日期：——
• THE SYNTHESIS OF SUBSTITUTED 5,6-BENZOCINCHONINIC ACIDS BY THE DOEBNER AND BY THE PFITZINGER REACTIONS^*
  作者：EDWIN ALLIN ROBINSON、MARSTON TAYLOR BOGERT

  DOI：10.1021/jo01230a006

  日期：1936.3
• Condensation of N-monosubstituted 2-naphthylamines, formaldehyde, and cyclic β-diketones. One-pot synthesis of 2,4-disubstituted derivatives of 1,2,3,4-tetrahydrobenzo[f]quinoline
  作者：A. P. Kadutskii、N. G. Kozlov

  DOI：10.1134/s1070428010090113

  日期：2010.9

  Various spirocyclic derivatives of 1,2,3,4-tetrahydrobenzo[f]quinoline containing substituents in the positions 2 and 4 of the ring were obtained by one-pot multicomponent condensation of available N-benzyl-2-naphthylamines, formaldehyde, and cyclic beta-diketones of cyclohexanedione series.
• KOZLOV, N. S.;ZHIXAREVA, O. D.;ANDREEVA, E. I.;ROZHKOVA, N. G.;KUKALENKO,+, VESTSI. AN BSSR. CEP. XIM. N., 1985, N 2, 59-65
  作者：KOZLOV, N. S.、ZHIXAREVA, O. D.、ANDREEVA, E. I.、ROZHKOVA, N. G.、KUKALENKO,+

  DOI：——

  日期：——
• Double C–S bond formation via C–H bond functionalization: synthesis of benzothiazoles and naphtho[2,1-d]thiazoles from N-substituted arylamines and elemental sulfur
  作者：Xiaoming Zhu、Yuzhong Yang、Genhua Xiao、Jianxin Song、Yun Liang、Guobo Deng

  DOI：10.1039/c7cc07366f

  日期：——

  A novel, atom economic, and environmentally friendly method for the synthesis of 2-substituted benzothiazoles and 2-substituted naphtho[2,1-d]yhiazoles from N-substituted arylamines and elemental sulfur has been developed under metal-free conditions. The reaction underwent the process of double C-S bonds formation through C-H bonds functionalization.

  在无金属条件下开发了一种新颖，原子经济，环保的方法，该方法可从N-取代的芳基胺和元素硫合成2-取代的苯并噻唑和2-取代的萘并[2,1-d]噻唑。该反应经历了通过CH键官能化形成双CS键的过程。