1-(naphthalen-2-ylmethyl)-1H-pyrrole | 51491-79-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(naphthalen-2-ylmethyl)-1H-pyrrole
• 英文别名: 1-(2-Naphthylmethyl)-pyrrol；1-(Naphthalen-2-ylmethyl)pyrrole
• CAS: 51491-79-3
• 化学式: C₁₅H₁₃N
• 分子量: 207.275
• InChiKey: UFRDCQSXFDTUTI-UHFFFAOYSA-N

物化性质

• 熔点：
  57-60 °C
• 沸点：
  354.7±11.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-(naphthalen-2-ylmethyl)-1H-pyrrole 、 3,3-bis(ethylthio)-1-phenylprop-2-en-1-one 在 三氟化硼乙醚 作用下， 以 乙腈 为溶剂， 20.0 ℃ 、100.0 kPa 条件下， 反应 14.0h， 以95%的产率得到3-(1-(naphthalen-1-ylmethyl)-1H-pyrrol-2-yl)-3-(1-(naphthalen-2-ylmethyl)-1H-pyrrol-2-yl)-1-phenylprop-2-en-1-one
  参考文献：
  名称：

  BF 3 ·OEt 2介导的α-氧代乙烯酮二硫缩醛对吡咯的烯基化

  摘要：

  有效地实现了BF 3 ·OEt 2介导的吡咯与α-氧代烯酮二硫缩醛的烯基化反应，提供了单取代和二取代的烯酮吡咯基缩醛。在使用N-未保护的吡咯的情况下，反应产生了烯酮联吡咯基乙缩醛以及N，O-螯合的BF 2络合物。单取代的产物实现了不同的CS转化，生成了N-杂环或多取代的烯烃。

  DOI：

  10.1016/j.tetlet.2015.05.102
• 作为产物：
  描述：

  1-(naphthalen-2-ylmethyl)pyrrolidine 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1-(naphthalen-2-ylmethyl)-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

• A New Method to N-Arylmethylenepyrroles from N-Acylpyrroles
  作者：Claudius D’Silva、Rifat Iqbal

  DOI：10.1055/s-1996-4247

  日期：1996.4

  An efficient general method for the preparation of N-arylmethylenepyrroles based on the reduction of N-acylpyrroles is reported. The reduction procedure described is sufficiently mild to make it applicable to a variety of sensitive acyl and heterocyclic acyl compounds where reduction results in cleavage of the C-N bond. The method can also be used in the preparation of pyrrole derivatives containing base sensitive protecting groups.

  报道了一种高效的通用方法，用于制备N-芳基亚甲基吡咯，该方法基于N-酰基吡咯的还原。所述还原过程温和到足以适用于多种敏感的酰基和杂环酰基化合物，因为还原会导致C-N键的断裂。该方法还可以用于含有对碱敏感保护基团的吡咯衍生物的制备。
• 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.
• BF3·OEt2-mediated alkenylation of pyrroles with α-oxo ketene dithioacetals
  作者：Xiaoge Yang、Kaikai Wu、Zhengkun Yu

  DOI：10.1016/j.tetlet.2015.05.102

  日期：2015.7

  BF3·OEt2-mediated alkenylation of pyrroles with α-oxo ketene dithioacetals was efficiently realized, affording mono- and disubstituted ketene pyrrolyl acetals. In the cases of using N-unprotected pyrrole, the reactions gave ketene bipyrrolyl acetals as well as N,O-chelated BF2 complexes. Diverse C–S transformations were achieved for the monosubstituted products, yielding N-heterocycles or multisubstituted

  有效地实现了BF 3 ·OEt 2介导的吡咯与α-氧代烯酮二硫缩醛的烯基化反应，提供了单取代和二取代的烯酮吡咯基缩醛。在使用N-未保护的吡咯的情况下，反应产生了烯酮联吡咯基乙缩醛以及N，O-螯合的BF 2络合物。单取代的产物实现了不同的CS转化，生成了N-杂环或多取代的烯烃。
• 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.