3,4-diphenyl-3-hydroxy-2-methyl-5-(2-methylethyl)-2-pyrroline

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 3,4-diphenyl-3-hydroxy-2-methyl-5-(2-methylethyl)-2-pyrroline
• 英文别名: 5-Methyl-3,4-diphenyl-2-propan-2-yl-2,3-dihydropyrrol-4-ol
• 化学式: C₂₀H₂₃NO
• 分子量: 293.409
• InChiKey: IOQACWAHDJJJPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  32.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  methyl (1E)-N-(2-methyl-1-tributylstannylpropyl)ethanimidate 、 triethyl-[(2R,3S)-5-ethyl-2-propan-2-yl-3,4-dihydro-2H-pyrrol-3-yl]silane 以22%的产率得到
  参考文献：
  名称：

  Pearson William H., Stevens Erland P., Tetrahedron Lett, 35 (1994) N 17, S 2641-2644

  摘要：

  DOI：

文献信息

• Generation and cycloaddition of heteroatom-substituted 2-azaallyl anions with alkenes and alkynes. Synthesis of 1-pyrrolines and pyrroles
  作者：William H. Pearson、Erland P. Stevens

  DOI：10.1016/s0040-4039(00)76994-2

  日期：1994.4

  heteroatom-substituted 2-azaallyl anions 2. These anions underwent [2πs+4πs] cycloadditions with alkenes to produce 1-pyrrolines 4 after loss of alkoxide or thiolate. The pyrrolines were further deprotonated in situ with n-BuLi to generate 1-metalloenamines 5, which could be quenched with water or CH3I to produce 1-pyrrolines 4 or 6. The use of diphenylacetylene in the cycloaddition resulted in the formation

  亚氨酸酯和thioimidates 1轴承的N-（1-三Ñ -butylstannyl）烷基（例如，7 - 9）用transmetalated Ñ正丁基锂，以产生杂原子取代的2-azaallyl阴离子2。这些阴离子与烯烃进行[2πs+4πs]环加成反应，在失去醇盐或硫醇盐后生成1-吡咯啉4。吡咯啉进一步用正丁基锂原位去质子化生成1-metalloenamines 5，可将其用水或CH 3 I淬灭，生成1-pyrorolines 4或6。在环加成反应中使用二苯基乙炔导致形成吡咯。
• Cycloaddition of Heteroatom-Substituted 2-Azaallyl Anions with Alkenes. Synthesis of 1-Pyrrolines and Bridged Azabicyclic Compounds
  作者：William H. Pearson、Erland P. Stevens

  DOI：10.1021/jo981457i

  日期：1998.12.1

  Nonstabilized 2-azaallyl anions bearing heteroatom substituents [(RCHNC)-C-1(X)R-2(-)Li(+), where R-1 and R-2 are hydrogen or alkyl groups and X = OMe, SPh, or NR2] were generated and found to undergo efficient [3 + 2] cycloadditions with alkenes to provide 1-pyrrolines after loss of LiX. The 2-azaallyl anions were generated by tin-lithium exchange on stannyl imidates, thioimidates, or amidines (RCH)-C-1(SnBu3)N=C(X)R-2 with n-butyllithium. The initially formed 1-pyrrolines were found to be deprotonated under the reaction conditions to afford 1-metalloenamines, which could be quenched with alkyl halides, carbonyl compounds, or MeSSMe to provide further functionalized 1-pyrrolines. Cyclic methoxy-substituted 2-azaallyl anions were generated and were found to undergo cycloadditions with alkenes to afford bridged azabicyclic compounds (1-methoxy-7-azabicyclo[2.2.1]heptanes and 1-methoxy-8-azabicyclo[3.2.1]octanes). These are the first examples of cyclic nonstabilized 2-azaallyl anions.