4-(吡咯-1-基甲基)吡啶 | 87451-35-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 4-(吡咯-1-基甲基)吡啶
• 英文名称: 4-((1H-pyrrol-1-yl)methyl)pyridine
• 英文别名: 3-(pyrrol-1-yl-methyl)pyridine；4-(1-pyrrolylmethyl)pyridine；4-(1H-pyrrol-1-ylmethyl)pyridine；4-(pyrrol-1-ylmethyl)pyridine
• CAS: 87451-35-2
• 化学式: C₁₀H₁₀N₂
• mdl: MFCD00119346
• 分子量: 158.203
• InChiKey: RMCRMKZIVXSMLL-UHFFFAOYSA-N

物化性质

• 沸点：
  278.2±15.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-(吡咯-1-基甲基)吡啶 在 platinum(IV) oxide sodium hydroxide 、 sodium tetrahydroborate 、 mercury(II) diacetate 、 氢气 作用下， 以 乙醇 、 丙酮 、 苯 为溶剂， 反应 54.17h， 生成 2-methyl-1,2,3,4,5,6-hexahydro-1,5-methanopyrrolo<1,2-a><1,4>diazocine
  参考文献：
  名称：

  Mercuric acetate cyclization of 4-(pyrrolylmethyl)- and 4-(indolylmethyl)piperidines to bridged polycyclic systems

  摘要：

  DOI：

  10.1021/jo00173a010
• 作为产物：
  描述：

  4-(pyrrolidin-1-ylmethyl)pyridine 在 β-环糊精 、 2-碘酰基苯甲酸 作用下， 以 水 为溶剂， 反应 8.0h， 以82%的产率得到4-(吡咯-1-基甲基)吡啶
  参考文献：
  名称：

  o-Iodoxybenzoic acid (IBX): a versatile reagent for the synthesis of N-substituted pyrroles mediated by β-cyclodextrin in water

  摘要：

  o-Iodoxybenzoic acid (IBX), a very mild and efficient hypervalent iodine(V) reagent, aromatizes diversely substituted 1-benzylpyrrolidines and N-substituted L-proline analogues to the corresponding substituted pyrroles in good to excellent yields under mild conditions mediated by beta-cyclodextrin in water at room temperature. To the best of our knowledge, this is the first report on IBX, promoting complete aromatization leading to N-benzylpyrroles from the corresponding saturated five membered heterocyclic derivatives in water medium. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.06.077

文献信息

• Substituted pyrrole mannich bases to combat pain and allergic reactions
  申请人：——

  公开号：US20030023100A1

  公开（公告）日：2003-01-30

  The invention relates to substituted pyrrole Mannich bases of general formula (I), wherein R 1 =H, a C 1-10 -alkyl-, aryl, a heteroaryl- or an aryl, heteroaryl-, CN, Br—, Cl or OH radical bound by a C 1-6 alkylene group, R 2 =CH(R 4 )N(R 5 )(R 6 ), R3, R3′, R3″ identically or individually represent H, F, Cl, Br, CF 3 , CN, NO 2 , SO 2 NH 2 , NHR′, SR 8 , OR 9 , CO(OR 10 ), CH 2 CO(OR 11 ), COR 15 , a C 1-10 -alkyl-, aryl-, heteroaryl- aryl radical or a heteroalkyl radical bound by a C 1-6 alkylene group, R 4 =an unsubstituted phenyl radical or a phenyl radical substituted at least with C 1-4 alkyl, C 1-3 -alkoxy-, halogen-, a method for the production of the above-mentioned compounds, medicaments containing said compounds, and the use of said compounds in the production of medicaments. Said active ingredients are particularly suitable for pain therapy, and for treating inflammatory and allergic reactions, drug or alcohol abuse, diarrhoea, gastritis, ulcers, cardiovascular diseases, urinary incontinence, depressions, states of shock, migranes, narcolepsy, overweight, asthma, glaucoma, hyperkinetic syndrome, lack of drive, bulimia, anorexia, catalepsia, anxiolysis increasing vigilance and/or increasing libido.

  本发明涉及一般式（I）的取代吡咯曼尼希碱，其中R1＝H，C1-10烷基，芳基，杂芳基或由C1-6烷基组成的芳基，杂芳基，CN，Br，Cl或OH基，R2＝CH（R4）N（R5）（R6），R3，R3'，R3''相同或分别代表H，F，Cl，Br，CF3，CN，NO2，SO2NH2，NHR'，SR8，OR9，CO（OR10），CH2CO（OR11），COR15，C1-10烷基，芳基，杂芳基，芳基基或由C1-6烷基组成的杂烷基，R4＝未取代苯基或至少取代C1-4烷基，C1-3-烷氧基，卤素基的苯基，制备上述化合物的方法，含有上述化合物的药物以及上述化合物在药物生产中的应用。这些活性成分特别适用于疼痛治疗，以及治疗炎症和过敏反应，药物或酒精滥用，腹泻，胃炎，溃疡，心血管疾病，尿失禁，抑郁症，休克状态，偏头痛，嗜睡症，超重，哮喘，青光眼，多动症，缺乏动力，暴食症，厌食症，弛压症，增加警觉性和/或增加性欲。
• Synthesis of N-alkyl pyrroles via decarboxylation/dehydration in neutral ionic liquid under catalyst-free conditions
  作者：Veena D. Yadav、Shashikant U. Dighe、Sanjay Batra

  DOI：10.1039/c4ra09797a

  日期：——

  A catalyst-free benign route toN-alkyl pyrroles by reacting aromatic, heteroaromatic or aliphatic aldehydes with 4-hydroxyproline in neutral ionic liquid under microwave irradiation is presented.

  本文介绍了一种无催化剂的温和方法，通过在中性离子液体中微波辐射下将芳香族、杂环或脂肪族醛与4-羟基脯氨酸反应，制备N-烷基吡咯。
• trans-4-Hydroxy-l-proline: a novel starting material for N-alkylpyrroles synthesis
  作者：A. Vijay Kumar、K. Rama Rao

  DOI：10.1016/j.tetlet.2011.04.045

  日期：2011.6

  resulting in the formation of N-alkylpyrroles in good to excellent yields, via decarboxylation followed by redox isomerization under neutral conditions. The neutral conditions allow access to efficient synthesis of N-alkyl pyrroles with high functional group tolerance.

  首次研究了醛与反式-4-羟基-1-脯氨酸的反应，通过脱羧，然后在中性条件下进行氧化还原异构化，以良好至极佳的收率形成了N-烷基吡咯。中性条件允许获得具有高官能团耐受性的N-烷基吡咯的有效合成。
• Electrochemical sensing of fluoride and sugars with a boronic acid-substituted bipyridine Fe(II) complex in solution and attached onto an electrode surface
  作者：M. Nicolas、B. Fabre、J. Simonet

  DOI：10.1016/s0013-4686(00)00694-0

  日期：2001.1

  The electrochemical behaviour of a boronic acid-substituted 2,2′-bipyridine 1 Fe(II) complex ([Fe(II)13]2+) has been investigated in aqueous buffered solutions, in the absence and in the presence of F− or various sugars as guest species. The binding of the halide to the boron atom led to a shift of the Fe(II)/Fe(III) oxidation peak towards less positive potentials whereas the sugars, and particularly

  硼酸取代的2,2'-联吡啶1 Fe（II）配合物（[Fe（II）1 3 ] 2+）的电化学行为已在水性缓冲溶液中，不存在和存在F的条件下进行了研究。−或各种糖作为客体。卤化物与硼原子的结合导致Fe（II）/ Fe（III）氧化峰向较小的正电位移动，而糖，尤其是d-果糖则具有相反的作用。为了开发电化学传感器，已经成功地由包含配体1和N的可电聚合的有机金属组件将这种氧化还原活性受体固定在电极表面上。取代的吡咯衍生物。其阳极氧化产生的聚合物膜在CH 3 CN中表现出稳定的电活性。由于在水性介质中的电活性的总损耗，F的唯一的作用-上的固定化的Fe（II）的反应/铁（III）系统已经在CH检查3 CN。在该客体阴离子的存在下，证实了一种异常的络合诱导的催化现象。
• An elegant protocol for the synthesis of N-substituted pyrroles through C–N cross coupling/aromatization process using CuFe2O4 nanoparticles as catalyst under ligand-free conditions
  作者：G. Satish、K. Harsha Vardhan Reddy、K. Ramesh、B.S.P. Anil Kumar、Y.V.D. Nageswar

  DOI：10.1016/j.tetlet.2014.01.075

  日期：2014.4

  A simple and efficient, ligand-free C-N cross-coupling of aryl halides/benzyl bromides with trans-4-hydroxy-L-proline has been developed to produce aromatized N-substituted pyrroles, using a catalytic amount of magnetically separable and recyclable CuFe2O4 nanoparticles, in the presence of Cs2CO3 in DMSO at 100 degrees C. (C) 2014 Elsevier Ltd. All rights reserved.