(S)-2-methyl-1,2,3,4-tetrahydroacridine | 1438401-58-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (S)-2-methyl-1,2,3,4-tetrahydroacridine
• 英文别名: (2S)-2-methyl-1,2,3,4-tetrahydroacridine
• CAS: 1438401-58-1
• 化学式: C₁₄H₁₅N
• 分子量: 197.28
• InChiKey: AZXXASKCSPTIJW-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-甲基环己酮 、 2-氨基苯甲醛 在 N-[(1S)-2'-[[(4-methylphenyl)sulfonyl]amino][1,1'-binaphthalen]-2-yl]-2-pyrrolidinecarboxamide 、 水 作用下， 以 neat (no solvent) 为溶剂， 反应 24.0h， 以89%的产率得到(S)-2-methyl-1,2,3,4-tetrahydroacridine
  参考文献：
  名称：

  Solvent-Free Enantioselective Friedländer Condensation with Wet 1,1′-Binaphthalene-2,2′-diamine-Derived Prolinamides as Organocatalysts

  摘要：

  Wet unsupported and supported 1,1'-binaphthalene-2,2'-diamine (BINAM) derived prolinamides are efficient organocatalysts under solvent-free conditions at room temperature to perform the synthesis of chiral tacrine analogues in good yields (up to 93%) and excellent enantioselectivies (up to 96%). The Friedlander reaction involved in this process takes place with several cyclohexanone derivatives and 2-aminoaromatic aldehydes, and it is compatible with the presence of either electron-withdrawing or electron-donating groups at the aromatic ring of the 2-aminoaryl aldehyde derivatives used as electrophiles. The reaction can be extended to cyclopentanone derivatives, affording a regioisomeric but separable mixture of products. The use of the wet silica gel supported organocatalyst, under solvent-free conditions, for this process led to the expected product (up to 87% enantiomeric excess), with its reuse being possible at least up to five times.

  DOI：

  10.1021/jo400522m

文献信息

• Solvent-Free Enantioselective Friedländer Condensation with Wet 1,1′-Binaphthalene-2,2′-diamine-Derived Prolinamides as Organocatalysts
  作者：Abraham Bañón-Caballero、Gabriela Guillena、Carmen Nájera

  DOI：10.1021/jo400522m

  日期：2013.6.7

  Wet unsupported and supported 1,1'-binaphthalene-2,2'-diamine (BINAM) derived prolinamides are efficient organocatalysts under solvent-free conditions at room temperature to perform the synthesis of chiral tacrine analogues in good yields (up to 93%) and excellent enantioselectivies (up to 96%). The Friedlander reaction involved in this process takes place with several cyclohexanone derivatives and 2-aminoaromatic aldehydes, and it is compatible with the presence of either electron-withdrawing or electron-donating groups at the aromatic ring of the 2-aminoaryl aldehyde derivatives used as electrophiles. The reaction can be extended to cyclopentanone derivatives, affording a regioisomeric but separable mixture of products. The use of the wet silica gel supported organocatalyst, under solvent-free conditions, for this process led to the expected product (up to 87% enantiomeric excess), with its reuse being possible at least up to five times.