(2R,4S)-dimethyl 2-methyl-4-(phenylamino)-1,2,3,4-tetrahydroquinoline-2,4-dicarboxylate | 1437308-03-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (2R,4S)-dimethyl 2-methyl-4-(phenylamino)-1,2,3,4-tetrahydroquinoline-2,4-dicarboxylate
• 英文别名: dimethyl (2R,4S)-4-anilino-2-methyl-1,3-dihydroquinoline-2,4-dicarboxylate
• CAS: 1437308-03-6
• 化学式: C₂₀H₂₂N₂O₄
• 分子量: 354.406
• InChiKey: ISGKZKXRQVZDAK-UXHICEINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  正丙胺 、 (2R,4S)-dimethyl 2-methyl-4-(phenylamino)-1,2,3,4-tetrahydroquinoline-2,4-dicarboxylate 在 溶剂黄146 作用下， 以 2,2,2-三氟乙醇 为溶剂， 以55%的产率得到(2R,5R)-methyl 7-methoxy-2-methyl-3-oxo-4-propyl-2,3,4,5-tetrahydro-1H-2,5-methanobenzo[e][1,4]diazepine-5-carboxylate
  参考文献：
  名称：

  A Highly Diastereo- and Enantioselective Synthesis of Tetrahydroquinolines: Quaternary Stereogenic Center Inversion and Functionalization

  摘要：

  Tetrahydroquinolines containing two quaternary stereogenic centers were synthesized with excellent ee and dr via a four-component cyclization reaction catalyzed by a chiral phosphoric acid. High chemoselectivity was achieved by differentiating anilines with similar reactivities to yield diverse hybrid products. The chirality of the quaternary C4 atom of the 4-aminotetrahydroquinoline products was found to undergo highly stereoselective inversion, enabling facile functionalization using a wide range of nucleophiles (C, O, N, and S).

  DOI：

  10.1021/ja4040945
• 作为产物：
  描述：

  丙酮酸甲酯 、 苯胺 在 C₄₈H₃₇O₄P 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以90%的产率得到(2R,4S)-dimethyl 2-methyl-4-(phenylamino)-1,2,3,4-tetrahydroquinoline-2,4-dicarboxylate
  参考文献：
  名称：

  A Highly Diastereo- and Enantioselective Synthesis of Tetrahydroquinolines: Quaternary Stereogenic Center Inversion and Functionalization

  摘要：

  Tetrahydroquinolines containing two quaternary stereogenic centers were synthesized with excellent ee and dr via a four-component cyclization reaction catalyzed by a chiral phosphoric acid. High chemoselectivity was achieved by differentiating anilines with similar reactivities to yield diverse hybrid products. The chirality of the quaternary C4 atom of the 4-aminotetrahydroquinoline products was found to undergo highly stereoselective inversion, enabling facile functionalization using a wide range of nucleophiles (C, O, N, and S).

  DOI：

  10.1021/ja4040945

文献信息

• Design, Synthesis, and Biological Evaluation of Chemically and Biologically Diverse Pyrroquinoline Pseudo Natural Products
  作者：Jie Liu、Gregor S. Cremosnik、Felix Otte、Axel Pahl、Sonja Sievers、Carsten Strohmann、Herbert Waldmann

  DOI：10.1002/anie.202013731

  日期：2021.2.23

  Natural product (NP) structures are a rich source of inspiration for the discovery of new biologically relevant chemical matter. In natural product inspired pseudo‐NPs, NP‐derived fragments are combined de novo in unprecedented arrangements. Described here is the design and synthesis of a 155‐member pyrroquinoline pseudo‐NP collection in which fragments characteristic of the tetrahydroquinoline and

  天然产物（NP）结构是发现新的生物学相关化学物质的丰富灵感来源。在天然产物激发的伪NP中，NP衍生的片段以前所未有的排列方式从头结合。这里描述的是155个成员的吡咯并喹啉假NP集合的设计和合成，其中四氢喹啉和吡咯烷NP类的特征片段结合了8种不同的连接性和区域异构排列。化学形态分析和通过形态学“细胞绘画”分析中的表型进行化合物收集的生物学评估，然后进行主成分分析，显示伪NP类在化学上是多种多样的，并且生物活性模式明显不同，