4-叠氮基-7-(三氟甲基)喹啉 | 74227-77-3

• 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
• 中文名称: 4-叠氮基-7-(三氟甲基)喹啉
• 英文名称: 4-azido-7-(trifluoromethyl)quinoline
• CAS: 74227-77-3
• 化学式: C₁₀H₅F₃N₄
• 分子量: 238.172
• InChiKey: CTHLYMHOLICEFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  27.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-叠氮基-7-(三氟甲基)喹啉 在 间氯过氧苯甲酸 作用下， 反应 30.0h， 以84%的产率得到4-azido-7-trifluoromethylquinoline 1-oxide
  参考文献：
  名称：

  Synthesis of 4-azidoquinoline 1-oxides and related compounds.

  摘要：

  合成了在2位有甲基、氰基和氨酰基，7位有氯和三氟甲基的4-叠氮喹啉1-氧化物。此外，还合成了4-叠氮喹唑1-氧化物和2-氧化物。它们的抗肿瘤和诱变活性与致癌、抗癌和诱变化合物4-硝基喹啉1-氧化物进行了比较测试。

  DOI：

  10.1248/cpb.28.1485
• 作为产物：
  描述：

  4-氯-7-三氟甲基喹啉 在 sodium azide 作用下， 以 乙醇 、 水 为溶剂， 以87%的产率得到4-叠氮基-7-(三氟甲基)喹啉
  参考文献：
  名称：

  Synthesis of 4-azidoquinoline 1-oxides and related compounds.

  摘要：

  合成了在2位有甲基、氰基和氨酰基，7位有氯和三氟甲基的4-叠氮喹啉1-氧化物。此外，还合成了4-叠氮喹唑1-氧化物和2-氧化物。它们的抗肿瘤和诱变活性与致癌、抗癌和诱变化合物4-硝基喹啉1-氧化物进行了比较测试。

  DOI：

  10.1248/cpb.28.1485

文献信息

• Iron‐Mediated Electrophilic Amination of Organozinc Halides using Organic Azides
  作者：Simon Graßl、Johannes Singer、Paul Knochel

  DOI：10.1002/anie.201911704

  日期：2020.1.2

  arylated substrates with full retention of configuration. To demonstrate the utility of this reaction, we prepared two amine derivatives of pharmaceutical relevance using this iron-mediated electrophilic amination as the key step.

  各种烷基，芳基和杂芳基锌卤化物都被高度官能化的烷基，芳基和杂环叠氮化物胺化。反应在FeCl3（0.5当量）存在下于50°C的条件下在1小时内平稳进行，从而以高收率提供了相应的仲胺。该方法扩展到了肽叠氮化物，并为芳构化底物提供了完全保留的构型。为了证明该反应的实用性，我们使用该铁介导的亲电子胺化反应为关键步骤，制备了两种具有药物相关性的胺衍生物。
• Savini; Massarelli; Chiasserini, Il Farmaco, 1994, vol. 49, # 10, p. 633 - 639
  作者：Savini、Massarelli、Chiasserini、Pellerano、Bruni

  DOI：——

  日期：——
• Structure–activity relationships for ferriprotoporphyrin IX association and β-hematin inhibition by 4-aminoquinolines using experimental and ab initio methods
  作者：Samkele Nsumiwa、David Kuter、Sergio Wittlin、Kelly Chibale、Timothy J. Egan

  DOI：10.1016/j.bmc.2013.04.040

  日期：2013.7

  In order to probe structure-activity relationships of association with ferriprotoporphyrin IX (logK) and inhibition of beta-hematin formation, a series of 4-aminoquinolines with varying substituents at the 7-position (X) have been synthesized. These have been further elaborated by introduction of two different R groups on the 4-amino nitrogen atom in the form of methyl (R = Me) and ethylamine (R = EtNH2) side chains. Data for a previously investigated series containing an N,N-diethyl-ethylamine side chain were also compared with the findings of this study. Experimentally, logK values for the simple 4-aminoquinoline series (R = H) were found to correlate with the hydrophobicity constant (pi) of the group X. The logK values for the series with R = Me and EtNH2 were found to correlate with those of the series with R = H. The log of the 50% beta-hematin inhibitory activity (log BHIA(50)) was found to correlate with logK and either meta (sigma(m)) or para (sigma(p)) Hammett constants for the series with R = Me and EtNH2, but not the simple series with R = H. To further improve predictability, correlations with ab initio electrostatic parameters, namely Mulliken and CHelpG charges were investigated. The best correlations were found with CHelpG charges which indicated that logK values can be predicted from the charges on atom H-8 and the group X in the quinolinium species computed in vacuum, while log BHIA50 values can be predicted from the CHelpG charges on C-7, C-8 and N-1 for the neutral species in vacuum. These correlations indicate that association and inhibition of beta-hematin formation are separately determined. They also suggest that electron withdrawing groups at the 7-position, but not necessarily hydrophobic groups are required for hemozoin inhibition. The upshot is that the correlations imply that considerably more hydrophilic hemozoin inhibitors are feasible. (C) 2013 Elsevier Ltd. All rights reserved.
• Savini; Massarelli; Pellerano, Il Farmaco, 1993, vol. 48, # 4, p. 515 - 528
  作者：Savini、Massarelli、Pellerano

  DOI：——

  日期：——
• Savini; Massarelli; Corti, Il Farmaco, 1994, vol. 49, # 5, p. 363 - 369
  作者：Savini、Massarelli、Corti、Chiasserini、Pellerano、Bruni

  DOI：——

  日期：——