N-(3-quinolinyl)piperidine | 78641-21-1

• 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: N-(3-quinolinyl)piperidine
• 英文别名: 3-Piperidinochinolin；3-piperidin-1-yl-quinoline；3-piperidino-quinoline；3-Piperidino-chinolin；3-Piperidin-1-ylquinoline
• CAS: 78641-21-1
• 化学式: C₁₄H₁₆N₂
• 分子量: 212.294
• InChiKey: IMQXBHUHSYXFSE-UHFFFAOYSA-N

物化性质

• 熔点：
  75-76 °C
• 沸点：
  372.8±15.0 °C(Predicted)
• 密度：
  1.122±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  16.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  哌啶 、 3-溴喹啉 在 copper(II) sulfate 作用下， 以22%的产率得到N-(3-quinolinyl)piperidine
  参考文献：
  名称：

  3-氨基喹啉的合成及反应行为

  摘要：

  3-氨基喹啉 (3) 由 3-溴喹啉与氨反应以良好的收率生产。3 的取代是通过卤代烷对其钠盐的作用或通过与芳香族和脂肪族酮的还原性烷基化来实现的。苯乙酮曼尼希碱被 3 胺化。3 不与甲基乙烯基酮和丙烯腈形成任何加成产物。添加到苯基缩水甘油酸衍生物导致形成相应的 β-苯基-异丝氨酸衍生物。

  DOI：

  10.1002/ardp.19813140515

文献信息

• Rapid Room Temperature Buchwald–Hartwig and Suzuki–Miyaura Couplings of Heteroaromatic Compounds Employing Low Catalyst Loadings
  作者：Oscar Navarro、Nicolas Marion、Jianguo Mei、Steven P. Nolan

  DOI：10.1002/chem.200600283

  日期：2006.6.23

  complexes for Suzuki-Miyaura and Buchwald-Hartwig cross-coupling reactions involving heteroaromatic halides at room temperature is reported. The first examples of room temperature Suzuki-Miyaura cross-coupling of deactivated aryl chlorides with alkenyl boronic acids are also disclosed. Terminal substitution at the allyl moiety of the palladium complex facilitates its activation at room temperature leading

  据报道，在室温下，涉及杂芳族卤化物的第二代[（NHC）Pd（R-烯丙基）Cl]络合物用于Suzuki-Miyaura和Buchwald-Hartwig交叉偶联反应。还公开了失活的芳基氯与烯基硼酸的室温Suzuki-Miyaura交叉偶联的第一个实例。钯配合物的烯丙基部分的末端取代促进其在室温下的活化，从而导致非常活跃的催化物质，使得能够使用非常温和的反应条件快速进行本催化转化。Buchwald-Hartwig芳基胺化的催化剂负载量可低至10 ppm，Suzuki-Miyaura反应的催化剂负载量可低至50 ppm。
• Complex base-induced generation of 3,4-dehydroquinoline: a new access to quinoline derivatives
  作者：Stéphanie Blanchard、Gérald Guillaumet、Paul Caubère

  DOI：10.1016/s0040-4039(01)01339-9

  日期：2001.10

  3,4-Dehydroquinoline was easily generated from 3-bromoquinoline and a complex base NaNH2-tBuONa. Nucleophilic condensation of amines and thiolates were performed in good yields. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Halogen Reactivities. III. Kinetic Study of Displacement Reactions of Haloquinolines with Piperidine
  作者：K. R. Brower、W. P. Samuels、J. W. Way、E. D. Amstutz

  DOI：10.1021/jo50018a004

  日期：1953.12.1
• Engineering the Excited-State Dynamics of 3-Aminoquinoline by Chemical Modification and Temperature Variation
  作者：Avinash Kumar Singh、Srijon Ghosh、Rajesh Kancherla、Anindya Datta

  DOI：10.1021/acs.jpcb.6b09939

  日期：2016.12.22

  The role of the amino group in the excited-state dynamics of 3-aminoquinoline (3AQ) has been investigated by comparison with its synthetic derivative 3-(piperidin-1-yl)-quinoline (3PQ). The absence of amino hydrogen atoms in 3PQ eliminates, to a large extent, the complexity of the excited-state processes observed in 3AQ, The polarity of the medium is found to be the most important determinant in the nonradiative rate constants of 3PQ, unlike in 3AQ where hydrogen bonding plays the most significant role. The nonradiative rate constants decrease with increase in micro polarity. This trend is opposite to what is usually observed with dipolar states. Temperature dependence of the fluorescence spectra and lifetime has been studied to understand this unexpected observation. An unusual redshift in the emission of 3AQ and 3PQ is observed in nonpolar media at low temperatures. This is surprising, as a process involving a barrier is expected to be hindered at low temperatures and be manifested in a blueshift of the spectra, due to the predominance of the locally excited (LE) state. Moreover, the variation of emission maxima of 3AQ with temperature is sigmoidal in nature, indicating the involvement of two distinct states. The counterintuitive observation of the predominance of the state with comparatively lower emission energy, at low temperatures, establishes the following: the photophysics in 3AQ is dominated by a LE state at room temperature in nonpolar media. This state is associated with rapid flip-flop of the amino group, which provides an efficient nonradiative channel of deactivation. At low temperatures, this flip-flop is hindered and the molecule can undergo intramolecular charge transfer (ICT), whereby the lower energy state is populated. In the case of 3PQ, the ICT state is the only one present, owing to the tertiary amino group.
• SCHOENEN B.; ZYMALKOWSKI F., ARCH. PHARM., 1981, 314, NO 5, 464-470
  作者：SCHOENEN B.、 ZYMALKOWSKI F.

  DOI：——

  日期：——

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