1-(3-chlorobenzyl)-1H-pyrrole

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(3-chlorobenzyl)-1H-pyrrole
• 英文别名: 1-[(3-Chlorophenyl)methyl]pyrrole
• 化学式: C₁₁H₁₀ClN
• mdl: MFCD16663038
• 分子量: 191.66
• InChiKey: RFHKSFUOXUSDNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  N-(m-chlorobenzyl)pyrrolidine 在 β-环糊精 、 2-碘酰基苯甲酸 作用下， 以 水 为溶剂， 反应 9.0h， 以76%的产率得到1-(3-chlorobenzyl)-1H-pyrrole
  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

• Synthesis and nuclear magnetic resonance spectroscopic studies of 1-arylpyrroles
  作者：Chang Kiu Lee、Jung Ho Jun、Ji Sook Yu

  DOI：10.1002/jhet.5570370104

  日期：2000.1

  A series of m- and p-substituted 1-phenyl, 1-benzyl, 1-benzoyl, and 1-(2-phenylethyl)pyrroles was prepared and their 1H and 13C nmr spectroscopic characteristics were examined. In general, good correlations were observed between the chemical shift values of the βH and the βC of pyrroles [except 1-(2-phenylethyl)pyrroles] and the Hammettt σ. The observation may be explained in terms of the electronic

  一系列的米-和p -取代的1-苯基，1-苄基，1-苯甲酰基，和1-（2-苯乙基）吡咯制备和它们的1 H和13 C NMR光谱特性进行了研究。一般情况下，被所述β的化学位移值之间观察到良好的相关性H和β吡咯C [除了1-（2-苯乙基）吡咯]和Hammetttσ。可以用取代基的电子效应来解释该观察结果，所述取代基通过吡咯环的βCs与m-和p之间的p轨道相互作用通过键和空间传输。苯环的Cs。还给出了苯环的1 H和13 C化学位移的1-吡咯基，1-吡咯基甲基和1-吡咯基取代基常数。
• Decarboxylative formation of N-alkyl pyrroles from 4-hydroxyproline
  作者：Indubhusan Deb、Daniel J. Coiro、Daniel Seidel

  DOI：10.1039/c1cc11560j

  日期：——

  N-Alkyl pyrroles are obtained in a single step from 4-hydroxyproline and aldehydes in just 15 min under microwave irradiation.

  在微波辐射下，仅用15分钟即可从4-羟基脯氨酸和醛一步获得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。
• 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.
• o-Iodoxybenzoic acid (IBX): a versatile reagent for the synthesis of N-substituted pyrroles mediated by β-cyclodextrin in water
  作者：S. Narayana Murthy、Y.V.D. Nageswar

  DOI：10.1016/j.tetlet.2011.06.077

  日期：2011.8

  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.

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