2-phenyl-4-n-butyl-pyrrole | 1128264-41-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-phenyl-4-n-butyl-pyrrole
• 英文别名: 4-n-butyl-2-phenyl-1H-pyrrole；4-butyl-2-phenyl-1H-pyrrole
• CAS: 1128264-41-4
• 化学式: C₁₄H₁₇N
• 分子量: 199.296
• InChiKey: QMVTUGBOCOSOIS-UHFFFAOYSA-N

物化性质

• 沸点：
  335.2±11.0 °C(Predicted)
• 密度：
  1.002±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  tert-butyl 3-n-butyl-2-methoxy-5-oxopyrrolidine-1-carboxylate 在 对甲苯磺酸 作用下， 以 四氢呋喃 、 二丁醚 、 水 、 N,N-二甲基甲酰胺 为溶剂， -78.0~150.0 ℃ 、827.39 kPa 条件下， 反应 1.17h， 生成 2-phenyl-4-n-butyl-pyrrole
  参考文献：
  名称：

  A facile synthesis of 5-alkoxypyrrol-2(5H)-ones using a modified aza-Achmatowicz oxidation

  摘要：

  An efficient approach to 2,4-disubstituted pyrroles has been uncovered and is based on an oxidative rearrangement of a furanyl carbamate followed by sequential reaction of the resulting 5-methoxypyrrol-2(5H)-one with various alkyl lithiates. The final step of the procedure involves heating the ring opened 1-methoxy-5-oxopentylcarbamate with a primary amine. The overall process can be carried out under mild conditions and complements existing methods to prepare 2,4-disubstituted pyrroles. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.03.011

文献信息

• 一锅法制备的2,4-二取代吡咯或2,3,4-三取 代吡咯及制备方法
  申请人：河南大学

  公开号：CN110283159B

  公开（公告）日：2020-09-29

  本发明提供了一锅法制备的2,3‑二取代吡咯或2,3,4‑三取代吡咯及其制备方法，酮肟与对甲苯磺酰氯在碱性条件下生成酮肟磺酸酯，酮肟磺酸酯不经分离，在该条件下发生Neber重排得到氮杂环丙烯中间体，氮杂环丙烯中间体与α位含质子的酮经开环和环化得到2,3‑二取代吡咯或2,3,4‑三取代吡咯。本发明首次提出酮肟与对甲苯磺酰氯在碱性条件下生成酮肟磺酸酯的方法，酮肟磺酸酯不经分离，在该条件下发生Neber重排得到的中间体与酮经开环和环化得到2,3‑二取代吡咯和2,3,4‑三取代吡咯的方法，不仅简化合成步骤，提高收率且扩大反应的适用范围。
• Synthesis of multisubstituted 1H-pyrrole: selenium-catalyzed reaction of γ-nitro substituted carbonyl compounds and carbon monoxide
  作者：Rui Umeda、Tsukasa Mashino、Yutaka Nishiyama

  DOI：10.1016/j.tet.2014.04.061

  日期：2014.7

  The novel and efficient selenium-catalyzed reductive N-heterocyclization of γ-nitro substituted carbonyl compounds with carbon monoxide has been developed. Various multisubstituted 1H-pyrroles can be easily prepared by this protocol. The one-pot synthesis of ethyl 1H-pyrrole-3-carboxylate derivatives was also successfully attained by the selenium-catalyzed reaction of β-ketoester, vinyl nitro compounds and

  已经开发出新颖和有效的硒催化一氧化碳对γ-硝基取代的羰基化合物进行硒催化的还原性N-杂环化。通过该方案可以容易地制备各种多取代的1 H-吡咯。通过硒催化β-酮酸酯，乙烯基硝基化合物和一氧化碳的反应，也成功地完成了1 H-吡咯-3-羧酸乙酯衍生物的一锅法合成。
• Synthesis of 2,4-Disubstituted Pyrroles by Rearrangements of 2-Furanyl Carbamates
  作者：Sezgin Kiren、Xuechuan Hong、Carolyn A. Leverett、Albert Padwa

  DOI：10.1021/ol900059e

  日期：2009.3.19

  2,4-Disubstituted pyrroles were synthesized by an oxidative rearrangement of a furanyl carbamate followed by sequential reaction of the resulting 5-methoxypyrrol-2(5H)-one with different alkyl lithiates. The final step of the procedure involves heating the ring opened 1-methoxy-5-oxopentylcarbamate with a primary amine.

  通过呋喃基氨基甲酸酯的氧化重排，然后使所得的5-甲氧基吡咯-2（5 H）-one与不同的烷基锂酸酯顺序反应，合成了2,4-二取代的吡咯。该方法的最后步骤涉及将开环的1-甲氧基-5-氧戊基氨基甲酸酯与伯胺一起加热。
• A facile synthesis of 5-alkoxypyrrol-2(5H)-ones using a modified aza-Achmatowicz oxidation
  作者：Sezgin Kiren、Xuechuan Hong、Carolyn A. Leverett、Albert Padwa

  DOI：10.1016/j.tet.2009.03.011

  日期：2009.8

  An efficient approach to 2,4-disubstituted pyrroles has been uncovered and is based on an oxidative rearrangement of a furanyl carbamate followed by sequential reaction of the resulting 5-methoxypyrrol-2(5H)-one with various alkyl lithiates. The final step of the procedure involves heating the ring opened 1-methoxy-5-oxopentylcarbamate with a primary amine. The overall process can be carried out under mild conditions and complements existing methods to prepare 2,4-disubstituted pyrroles. (C) 2009 Elsevier Ltd. All rights reserved.