5-butyl-3-hex-1-ynyl-2-isobutyl-pyrrole-1-carboxylic acid tert-butyl ester | 1429939-02-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 5-butyl-3-hex-1-ynyl-2-isobutyl-pyrrole-1-carboxylic acid tert-butyl ester
• 英文别名: N-Boc-5-butyl-3-hex-1-ynyl-2-isobutylpyrrole；Tert-butyl 5-butyl-3-hex-1-ynyl-2-(2-methylpropyl)pyrrole-1-carboxylate
• CAS: 1429939-02-5
• 化学式: C₂₃H₃₇NO₂
• 分子量: 359.552
• InChiKey: TVIXNJBJUWHTOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (2-hex-1-ynyl-2-hydroxy-1-(S)-isobutyl-oct-3-ynyl)carbamic acid tert-butyl ester 在 platinum(II) chloride 作用下， 反应 0.5h， 以99%的产率得到5-butyl-3-hex-1-ynyl-2-isobutyl-pyrrole-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  聚乙二醇作为铂或金催化的环化异构反应的基质：机理研究

  摘要：

  多样性设计：设计了一种基于PEG-3400和金属盐（Pt或Au）的新型催化体系，可以在微波辐射下有效地进行环异构化反应，经过沉淀/过滤后，该杂环化合物可以以优良的产率获得优异的多样化杂环（请参阅方案）。

  DOI：

  10.1002/chem.201203800

文献信息

• Copper-Catalyzed Synthesis of Substituted Furans and Pyrroles by Heterocyclodehydration and Tandem Heterocyclodehydration–Hydration of 3-Yne-1,2-diols and 1-Amino-3-yn-2-ol Derivatives
  作者：Bartolo Gabriele、Lucia Veltri、Pierluigi Plastina、Raffaella Mancuso、Mabel V. Vetere、Vito Maltese

  DOI：10.1021/jo400533j

  日期：2013.5.17

  CuCl2-catalyzed heterocyclodehydration of readily available 3-yne-1,2-diols and 1-amino-3-yn-2-ol derivatives afforded substituted furans and pyrroles, respectively, in good to high yields (53-99%) under mild conditions (MeOH as the solvent, 80-100 degrees C, 1-24 h). In the case of 2,2-dialkynyl-1,2-diols, bearing an additional alkynyl substituent at C-2, a cascade process, corresponding to copper-catalyzed heterocyclodehydration followed by acid-catalyzed hydration of the triple bond, was realized when the reaction was carried out in the presence of both CuCl2 and TsOH, leading to 3-acylfurans in one step and high yields (75-84%). Under the same conditions, N-Boc-2-alkynyl-1-amino-3-yn-2-ols were converted into the corresponding N-unsubstituted 3-acylpyrroles in low to fair yields (19-59%). However, working in the presence of added water and a large excess of CO2 (40 atm), in addition to CuCl2 and TsOH, caused a significant improvement of the yields of 3-acylpyrroles (68-87%), thus making the method of general synthetic applicability.