(S)-N-Boc-4-amino-6-methyl-1-trimethylsilanyl-3-trimethylsilanylethynylhept-1-yn-3-ol | 1431620-47-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-N-Boc-4-amino-6-methyl-1-trimethylsilanyl-3-trimethylsilanylethynylhept-1-yn-3-ol
• 英文别名: tert-butyl N-[(4S)-3-hydroxy-6-methyl-1-trimethylsilyl-3-(2-trimethylsilylethynyl)hept-1-yn-4-yl]carbamate
• CAS: 1431620-47-1
• 化学式: C₂₁H₃₉NO₃Si₂
• 分子量: 409.717
• InChiKey: YDIBVHKUCFIECL-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.42
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-N-Boc-4-amino-6-methyl-1-trimethylsilanyl-3-trimethylsilanylethynylhept-1-yn-3-ol 在 二氧化碳 、 水 、 potassium carbonate 、 对甲苯磺酸 、 copper dichloride 作用下， 以 甲醇 为溶剂， 20.0~100.0 ℃ 、4.05 MPa 条件下， 反应 30.0h， 生成 1-(2-isobutylfuran-3-yl)ethanone
  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
• 作为产物：
  描述：

  溴乙烷 、 BOC-L-亮氨酸甲酯 、 三甲基乙炔基硅 在 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 2.58h， 以77%的产率得到(S)-N-Boc-4-amino-6-methyl-1-trimethylsilanyl-3-trimethylsilanylethynylhept-1-yn-3-ol
  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

• 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.