(R)-2-phenyl-1,2,3,4-tetrahydroacridine | 1345510-92-0

• 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: (R)-2-phenyl-1,2,3,4-tetrahydroacridine
• 英文别名: 2-phenyl-1,2,3,4-tetrahydroacridine；(2R)-2-phenyl-1,2,3,4-tetrahydroacridine
• CAS: 1345510-92-0
• 化学式: C₁₉H₁₇N
• 分子量: 259.351
• InChiKey: MAVXZXSEKRXRBC-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 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：

  2-氨基苯甲醛 在 (R)-2,6-di([1,1'-biphenyl]-4-yl)-4-hydroxydinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepine-4-oxide 、 magnesium sulfate 作用下， 以 甲苯 为溶剂， 反应 2.5h， 生成 (R)-2-phenyl-1,2,3,4-tetrahydroacridine
  参考文献：
  名称：

  Brønsted acid-catalyzed enantioselective Friedländer condensations: achiral amine promoter plays crucial role in the stereocontrol

  摘要：

  通过使用手性布伦司特酸和非手性胺，建立了一种高对映体选择性的弗里德兰德缩合反应，以高产率（高达 99%）和优异的对映体选择性（高达 95%）得到喹啉类化合物。

  DOI：

  10.1039/c1cc14873g

文献信息

• Catalytic Enantioselective Friedländer Condensations: Facile Access to Quinolines with Remote Stereogenic Centers
  作者：Le Li、Daniel Seidel

  DOI：10.1021/ol1023932

  日期：2010.11.5

  Enamine catalysis enables the first catalytic enantioselective Friedländer reaction. The desymmetrization of 4-substituted cyclohexanones upon reaction with o-aminobenzaldehydes allows for the synthesis of quinolines with remote stereogenic centers. These heterocycles, which are obtained with high levels of enantioselectivity, serve as precursors for chiral tacrine analogues.

  烯胺催化可实现第一个催化对映选择性弗里德兰德反应。与邻氨基苯甲醛反应后，4-取代的环己酮的脱对称化使得可以合成具有远程立体中心的喹啉。这些具有高水平对映选择性的杂环用作手性他克林类似物的前体。
• 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.
• Brønsted acid-catalyzed enantioselective Friedländer condensations: achiral amine promoter plays crucial role in the stereocontrol
  作者：Lei Ren、Tao Lei、Liu-Zhu Gong

  DOI：10.1039/c1cc14873g

  日期：——

  A highly enantioselective Friedländer condensation has been established by using chiral Brønsted acids in combination with achiral amines to give quinolines in high yields (up to 99%) and with excellent enantioselectivities (up to 95%).

  通过使用手性布伦司特酸和非手性胺，建立了一种高对映体选择性的弗里德兰德缩合反应，以高产率（高达 99%）和优异的对映体选择性（高达 95%）得到喹啉类化合物。