2-heptylquinoline | 83260-97-3

• 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
• 英文名称: 2-heptylquinoline
• 英文别名: 2-n-Heptylquinoline
• CAS: 83260-97-3
• 化学式: C₁₆H₂₁N
• 分子量: 227.349
• InChiKey: JICASAJSLGNZKP-UHFFFAOYSA-N

物化性质

• 沸点：
  118-122 °C(Press: 0.2 Torr)
• 密度：
  0.979±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-heptylquinoline 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 反应 12.0h， 以81%的产率得到2-n-heptyl-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  Synthesis, Structure-Activity Relationships, and Pharmacological Evaluation of Pyrrolo[3,2,1-ij]quinoline Derivatives: Potent Histamine and Platelet Activating Factor Antagonism and 5-Lipoxygenase Inhibitory Properties. Potential Therapeutic Application in Asthma

  摘要：

  A series of pyrrolo[3,2,1-ij]quinoline derivatives was synthesized and evaluated for their in vitro and in vivo activities against histamine, platelet activating factor (PAF), and leukotrienes which are recognized to be of importance in asthma. The structure-activity relationship studies have shown that the optimum moiety on the 1-position of the pyrroloquinoline nucleus is a 2-[4-(4-methyl-2-pyridinyl)-1-piperazinyl]ethyl chain in conjunction with a methyl group on the 2-position for potent antagonism of both histamine and PAF. The introduction of substituents on the 8- and 4-positions was also investigated in order to increase the potency of 5-lipoxygenase inhibition while retaining or improving the activities against histamine and PAF. This series is exemplified by 4-n-butyl-5,6-dihydro-8-hydroxy-2-methyl-1-[2-[4-(4-methyl- 2-pyridinyl)-1-piperazinyl]ethyl]-4H-pyrrolo[3,2,1-ij]quinoline (24, KC 11404) which was found to be active against all three of the selected mediators. Compound 24 was found to be orally active in guinea pig models against the histaminic phase of antigen-induced bronchospasm and PAF-induced bronchoconstriction (ED(50) = 1.9 and 2.1 mu mol/kg, respectively). When tested against the leukotriene-dependent phase of the antigen-induced bronchoconstriction, compound 24 showed the same potency as zileuton.

  DOI：

  10.1021/jm00004a013
• 作为产物：
  描述：

  2-壬酮 在 氢氧化钾 、 铜 作用下， 生成 2-heptylquinoline
  参考文献：
  名称：

  Buu-Hoi; Jacquignon, Bulletin de la Societe Chimique de France, 1958, p. 1567

  摘要：

  DOI：

文献信息

• Iron-catalysed alkylation of 2-methyl and 4-methyl azaarenes with alcohols <i>via</i> C–H bond activation
  作者：Lalit Mohan Kabadwal、Sourajit Bera、Debasis Banerjee

  DOI：10.1039/d0cc01593h

  日期：——

  The first Fe-catalysed alkylation of 2-methyl and 4-methyl-azaarenes with a series of alkyl and hetero-aryl alcohols is reported (>39 examples and up to 95% yield). Multi-functionalisation of pyrazines and synthesis of anti-malarial drug (±) Angustureine significantly broaden the scope of this methodology. Preliminary mechanistic investigation, deuterium labeling and kinetic experiments including trapping

  报道了用一系列烷基和杂芳基醇进行的第一个Fe催化的2-甲基和4-甲基氮杂氮杂芳烃的烷基化反应（> 39个实例，收率高达95％）。吡嗪的多功能化和抗疟药（±）安格西汀的合成大大拓宽了该方法的范围。初步的机理研究，氘标记和动力学实验（包括捕集烯胺中间体1a'）特别重要。
• Cobalt-catalyzed alkylation of methyl-substituted N-heteroarenes with primary alcohols: direct access to functionalized N-heteroaromatics
  作者：Anju Mishra、Ambikesh D. Dwivedi、Sujan Shee、Sabuj Kundu

  DOI：10.1039/c9cc08448g

  日期：——

  Phosphine free, air and moisture stable Co(NNN) complex catalyzed alkylation of various methyl-substituted N-heteroarenes with alcohols is reported. Following the borrowing hydrogen methodology, a variety of methyl-substituted N-heteroarenes can be functionalized efficiently. To understand the mechanism of this reaction various kinetic and control experiments were carried out.

  据报道，无磷，空气和水分稳定的Co（NNN）络合物催化了各种甲基取代的N-杂芳烃与醇的烷基化反应。遵循借用氢方法，可以有效地官能化各种甲基取代的N-杂芳烃。为了理解该反应的机理，进行了各种动力学和控制实验。
• The preparation of a Co@C₃N₄ catalyst and applications in the synthesis of quinolines from 2-aminobenzyl alcohols with ketones
  作者：Fei Cao、Anruo Mao、Bobin Yang、Chenyang Ge、Dawei Wang

  DOI：10.1039/d0nj05767c

  日期：——

  recyclable catalyst, which could easily be reused. Therefore, a heterogeneous catalyst was synthesized through Co-doping of C3N4, and the Co-nanoparticles on C3N4 revealed high catalytic activity for the synthesis of quinolines with good recovery performance.

  合成了不对称的二苯基膦基吡啶基三唑配体，并通过红外，核磁共振和质谱对其进行了表征，并制备了相应的地球上富金属的金属配合物（钴）。考虑到能源消耗和环境友好性，有必要将这种二苯基膦基-吡啶基-三唑钴配合物转变为可循环使用的催化剂，以使其易于再利用。因此，非均相催化剂通过的C CO掺杂合成3 Ñ 4，和C上的钴纳米颗粒3 Ñ 4显示高的催化活性为具有良好的恢复性能喹啉的合成。
• PROCESS FOR PRODUCTION OF BIS-QUATERNARY AMMONIUM SALT, AND NOVEL INTERMEDIATE
  申请人：Okamoto Kuniaki

  公开号：US20120130107A1

  公开（公告）日：2012-05-24

  Object To provide a method for producing a bis-quaternary ammonium salt efficiently and a novel synthetic intermediate thereof. Solution The present invention relates to a method for producing a bis-quaternary ammonium salt represented by a general formula [3] which comprises reacting a disulfonic acid ester represented by a general formula [1] (in the formula, definitions of two R 1 's and T are as described in claim 1 ) with a tertiary amine represented by a general formula [2] (in the formula, definitions of R 3 to R 5 are as described in claim 1 ), and a disulfonic acid ester represented by a general formula [1′] (in the formula, two R 16 's represent independently a halogen atom or a C1-C3 fluoroalkyl group, and two m's represent independently an integer of 1 to 5).

  提供一种高效生产双季铵盐和其新型合成中间体的方法。本发明涉及一种生产由通用式[3]表示的双季铵盐的方法，包括将由通用式[1]表示的二磺酸酯（在该式中，两个R1和T的定义如权利要求1中所述）与由通用式[2]表示的三级胺（在该式中，R3到R5的定义如权利要求1中所述）以及由通用式[1']表示的二磺酸酯（在该式中，两个R16独立表示卤原子或C1-C3氟烷基，两个m独立表示1至5的整数）反应。
• Expeditious preparation of 2-substituted quinolines
  作者：Mohamed A Fakhfakh、Xavier Franck、Alain Fournet、Reynald Hocquemiller、Bruno Figadère

  DOI：10.1016/s0040-4039(01)00604-9

  日期：2001.6

  A library of 2-substituted quinolines was synthesized in solution from mixtures of Grignard reagents and a quinolinium salt. Grignard reagents were prepared in one pot, taking advantage of the entrainment method for their preparation from unreactive alkyl halides. Then mixtures of 2-alkylquinolines were readily accessible for biological tests or separated by centrifugal-partition chromatography (CPC)

  由格氏试剂和喹啉盐的混合物在溶液中合成了2-取代的喹啉文库。格利雅试剂在一个锅中制备，利用了从非反应性烷基卤化物制备的夹带方法。然后2-烷基喹啉的混合物易于进行生物学测试，或在进行生物学筛选之前通过离心分配色谱法（CPC）进行分离。