N-tosyl-5-butyl-3-hex-1-ynyl-2-methylpyrrole | 1234906-62-7

• 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: N-tosyl-5-butyl-3-hex-1-ynyl-2-methylpyrrole
• 英文别名: 5-Butyl-3-hex-1-ynyl-2-methyl-1-(4-methylphenyl)sulfonylpyrrole；5-butyl-3-hex-1-ynyl-2-methyl-1-(4-methylphenyl)sulfonylpyrrole
• CAS: 1234906-62-7
• 化学式: C₂₂H₂₉NO₂S
• 分子量: 371.544
• InChiKey: UFSVJRHJGKCWKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  47.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (S)-N-tosyl-7-(1-aminoethyl)trideca-5,8-diyn-7-ol 在 copper dichloride 作用下， 以 甲醇 为溶剂， 反应 8.0h， 以83%的产率得到N-tosyl-5-butyl-3-hex-1-ynyl-2-methylpyrrole
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1021/jo400533j

文献信息

• A simple and convenient synthesis of substituted furans and pyrroles by CuCl2-catalyzed heterocyclodehydration of 3-yne-1,2-diols and N-Boc- or N-tosyl-1-amino-3-yn-2-ols
  作者：Bartolo Gabriele、Pierluigi Plastina、Mabel V. Vetere、Lucia Veltri、Raffaella Mancuso、Giuseppe Salerno

  DOI：10.1016/j.tetlet.2010.05.001

  日期：2010.7

  A simple and economical synthesis of substituted furans and pyrroles, by ligand-free CuCl2-catalyzed heterocyclodehydration of readily available 3-yne-1,2-diols and N-Boc- or N-tosyl-1-amino-3-yn-2-ols, respectively, is presented. Reactions are carried out in MeOH at 80–100 °C for 1–24 h and afford the corresponding heterocyclic derivatives in 53–99% isolated yields.

  一种简单经济的取代呋喃和吡咯的合成方法，该方法通过无配体的CuCl 2催化的易获得的3-炔-1,2-二醇和N - Boc-或N-甲苯磺酰基-1-氨基-3-yn-的杂环脱水分别给出了2-ols。反应在MeOH中于80-100°C下进行1-24h，并以53-99％的分离产率得到相应的杂环衍生物。
• An efficient and general synthesis of pyrroles
  作者：Christopher M. Sharland、Jirada Singkhonrat、Muhammad NajeebUllah、Simon J. Hayes、David W. Knight、Damian G. Dunford

  DOI：10.1016/j.tetlet.2011.02.085

  日期：2011.5

  We have discovered that a wide range of 3-alkynyl-hydroxyalkanamine derivatives undergo 5-endo-dig cyclisations when exposed to silver nitrate supported on silica gel. Subsequent in situ dehydration of the resulting and sometimes isolable hydroxy-dihydropyrroles leads to pyrroles in essentially quantitative yields using this recoverable and reusable heterogeneous catalyst.

  我们已经发现，一个宽范围的3 -炔基hydroxyalkanamine衍生物经历5-内切-Dig环化当暴露于载于硅胶上的硝酸银。随后，使用这种可回收和可重复使用的非均相催化剂，所得的，有时是可分离的羟基-二氢吡咯的原位脱水导致吡咯以基本上定量的产率产生。
• 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.