4-N-pyrrolylbutane-1,2-diol | 106710-17-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 4-N-pyrrolylbutane-1,2-diol
• 英文别名: 4-pyrrol-1-ylbutane-1,2-diol
• CAS: 106710-17-2
• 化学式: C₈H₁₃NO₂
• 分子量: 155.197
• InChiKey: HHDWOOIJGKLKFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.23
• 重原子数：
  11.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  45.39
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-N-pyrrolylbutane-1,2-diol 在 吡啶 、 4-二甲氨基吡啶 、 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 48.25h， 生成 1-(2-(oxiran-2-yl)ethyl)-1H-pyrrole
  参考文献：
  名称：

  Pyrroles as terminators in cationic cyclizations. The preparation of 5,6,7,8-tetrahydroindolizidines and 6,7,8,9-tetrahydro-5H-pyrrolo[1,2-a]azepines

  摘要：

  DOI：

  10.1021/jo00381a021
• 作为产物：
  描述：

  4-N-pyrrolyl-1,2-O-isopropylidenebutane-1,2-diol 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 1.17h， 以86%的产率得到4-N-pyrrolylbutane-1,2-diol
  参考文献：
  名称：

  Exploratory Studies on Reactions of Cobaloxime π-Cations with C-Nucleophiles:  Irreversible Alkene Decomplexation versus Nucleophilic Capture

  摘要：

  (beta-Hydroxyalkyl)- and (beta-acetoxyalkyl)cobaloximes can undergo facile acid-catalyzed P-heteroatom exchange with oxygen and nitrogen nucleophiles in an S(N)1-like mechanism via cationic metal-alkene pi-complex intermediates (cobaloxime pi-cations). The reaction of cobaloxime pi-cations with carbon nucleophiles has not been previously reported. The results reported in this paper demonstrate that cobaloxime pi-cations are reasonably good electrophiles. They are sufficiently reactive to add to the electron-rich sp(2) centers in allyltrimethylsilane and pyrrole. A major side reaction for intermolecular reactions is irreversible alkene decomplexation. An intramolecular pyrrole cyclization (22 to 23, 83% yield) significantly raised the yield for nucleophilic addition compared to that of the analogous intermolecular couplings (12b tb 13b, 32% yield and 17 to 18, 29% yield). The results of these studies provide a foundation for the design and evaluation of modified cobalt ligands with the goal of suppressing alkene decomplexation and enhancing reaction of cobaloxime pi-cations with C-nucleophiles.

  DOI：

  10.1021/jo951319i

文献信息

• TANIS S. P.; RAGGON J. W., J. ORG. CHEM., 52,(1987) N 5, 819-827
  作者：TANIS S. P.、 RAGGON J. W.

  DOI：——

  日期：——
• Exploratory Studies on Reactions of Cobaloxime π-Cations with C-Nucleophiles:  Irreversible Alkene Decomplexation versus Nucleophilic Capture
  作者：Jennifer L. Gage、Bruce P. Branchaud

  DOI：10.1021/jo951319i

  日期：1996.1.1

  (beta-Hydroxyalkyl)- and (beta-acetoxyalkyl)cobaloximes can undergo facile acid-catalyzed P-heteroatom exchange with oxygen and nitrogen nucleophiles in an S(N)1-like mechanism via cationic metal-alkene pi-complex intermediates (cobaloxime pi-cations). The reaction of cobaloxime pi-cations with carbon nucleophiles has not been previously reported. The results reported in this paper demonstrate that cobaloxime pi-cations are reasonably good electrophiles. They are sufficiently reactive to add to the electron-rich sp(2) centers in allyltrimethylsilane and pyrrole. A major side reaction for intermolecular reactions is irreversible alkene decomplexation. An intramolecular pyrrole cyclization (22 to 23, 83% yield) significantly raised the yield for nucleophilic addition compared to that of the analogous intermolecular couplings (12b tb 13b, 32% yield and 17 to 18, 29% yield). The results of these studies provide a foundation for the design and evaluation of modified cobalt ligands with the goal of suppressing alkene decomplexation and enhancing reaction of cobaloxime pi-cations with C-nucleophiles.
• Pyrroles as terminators in cationic cyclizations. The preparation of 5,6,7,8-tetrahydroindolizidines and 6,7,8,9-tetrahydro-5H-pyrrolo[1,2-a]azepines
  作者：Steven P. Tanis、Jeffrey W. Raggon

  DOI：10.1021/jo00381a021

  日期：1987.3