4-Carboxy-2-phenyl-5,6,7,8-tetrahydroquinoline | 244090-26-4

• 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: 4-Carboxy-2-phenyl-5,6,7,8-tetrahydroquinoline
• 英文别名: 2-phenyl-5,6,7,8-tetrahydroquinoline-4-carboxylic acid；2-Phenyl-5,6,7,8-tetrahydroquinoline-4-carboxylic acid
• CAS: 244090-26-4
• 化学式: C₁₆H₁₅NO₂
• 分子量: 253.301
• InChiKey: MLKDLWCVMFFTOE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  50.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-(-)-1-苯丙胺 、 4-Carboxy-2-phenyl-5,6,7,8-tetrahydroquinoline 在 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 16.0h， 以35%的产率得到2-phenyl-N-[(1S)-1-phenylpropyl]-5,6,7,8-tetrahydroquinoline-4-carboxamide
  参考文献：
  名称：

  Replacement of the quinoline system in 2-phenyl-4-quinolinecarboxamide NK-3 receptor antagonists

  摘要：

  Results from a medicinal chemistry approach aimed at replacing the quinoline ring system in the potent and selective human neurokinin-3 (hNK-3) receptor antagonists 1-4 of general formula I are discussed. The data give further insight upon the potential NK-3 pharmacophore. In particular, it is highlighted that both the benzene-condensed ring and the quinoline nitrogen are crucial determinants for optimal binding affinity to the hNK-3 receptor. Some novel compounds maintained part of the binding affinity to the receptor (5, 6, 10 and 13) and compound 5, featuring the naphthalene ring system, appears to be suitable for further modifications; it offers the option to introduce electron-withdrawing groups at position 2 and 4, conferring on the ring an overall electron-deficiency similar to that of the quinoline. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(99)00043-9
• 作为产物：
  描述：

  苯甲醯乳酸 在 氢氧化钾 、 ammonium acetate 、 水 、 碳酸氢钠 、 对甲苯磺酸 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 23.0h， 生成 4-Carboxy-2-phenyl-5,6,7,8-tetrahydroquinoline
  参考文献：
  名称：

  Replacement of the quinoline system in 2-phenyl-4-quinolinecarboxamide NK-3 receptor antagonists

  摘要：

  Results from a medicinal chemistry approach aimed at replacing the quinoline ring system in the potent and selective human neurokinin-3 (hNK-3) receptor antagonists 1-4 of general formula I are discussed. The data give further insight upon the potential NK-3 pharmacophore. In particular, it is highlighted that both the benzene-condensed ring and the quinoline nitrogen are crucial determinants for optimal binding affinity to the hNK-3 receptor. Some novel compounds maintained part of the binding affinity to the receptor (5, 6, 10 and 13) and compound 5, featuring the naphthalene ring system, appears to be suitable for further modifications; it offers the option to introduce electron-withdrawing groups at position 2 and 4, conferring on the ring an overall electron-deficiency similar to that of the quinoline. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(99)00043-9

文献信息

• Organocatalytic Modified Guareschi–Thorpe Type Regioselective Synthesis: A Unified Direct Access to 5,6,7,8-Tetrahydroquinolines and Other Alicyclic[<i>b</i>]-Fused Pyridines
  作者：Pradeep K. Jaiswal、Vashundhra Sharma、Manas Mathur、Sandeep Chaudhary

  DOI：10.1021/acs.orglett.8b02132

  日期：2018.10.5

  An unprecedented organocatalytic, regioselective, modified Guareschi–Thorpe type protocol toward the modular synthesis of 5,6,7,8-tetrahydroquinolines 22a–g and other alicyclic[b]-fused pyridines 23–28 via the identification of Chitosan as a heterogeneous catalyst is reported. This novel strategy is operationally simple and showed a wide range of functional group tolerance and substrate compatibility

  前所未有的有机催化，区域选择性，改良的Guareschi-Thorpe型方案，通过鉴定壳聚糖作为多相催化剂，可模块化合成5,6,7,8-四氢喹啉22a – g和其他脂环式[ b ]稠合吡啶23 – 28。被报道。这种新颖的策略操作简单，并且具有广泛的官能团耐受性和底物相容性。拟议的机制途径涉及亚胺-烯胺级联方法，用于合成结构多样的脂环式[ b ]稠合吡啶杂环。新型抗真菌分子的克级合成和鉴定29 –图31强调了这种方法的实用性。
• Replacement of the quinoline system in 2-phenyl-4-quinolinecarboxamide NK-3 receptor antagonists
  作者：G.A.M Giardina、M Artico、S Cavagnera、A Cerri、E Consolandi、S Gagliardi、D Graziani、M Grugni、D.W.P Hay、M.A Luttmann、R Mena、L.F Raveglia、R Rigolio、H.M Sarau、D.B Schmidt、G Zanoni、C Farina

  DOI：10.1016/s0014-827x(99)00043-9

  日期：1999.6

  Results from a medicinal chemistry approach aimed at replacing the quinoline ring system in the potent and selective human neurokinin-3 (hNK-3) receptor antagonists 1-4 of general formula I are discussed. The data give further insight upon the potential NK-3 pharmacophore. In particular, it is highlighted that both the benzene-condensed ring and the quinoline nitrogen are crucial determinants for optimal binding affinity to the hNK-3 receptor. Some novel compounds maintained part of the binding affinity to the receptor (5, 6, 10 and 13) and compound 5, featuring the naphthalene ring system, appears to be suitable for further modifications; it offers the option to introduce electron-withdrawing groups at position 2 and 4, conferring on the ring an overall electron-deficiency similar to that of the quinoline. (C) 1999 Elsevier Science S.A. All rights reserved.