(4S,5R)-5-(1-methylpropa-1,2-dienyl)-4-(tert-butyldimethylsilyloxy)pyrrolidin-2-one | 359012-60-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (4S,5R)-5-(1-methylpropa-1,2-dienyl)-4-(tert-butyldimethylsilyloxy)pyrrolidin-2-one
• CAS: 359012-60-5
• 化学式: C₁₄H₂₅NO₂Si
• 分子量: 267.443
• InChiKey: HGOQBWTZLXLETR-WCQYABFASA-N

物化性质

• 沸点：
  350.0±42.0 °C(Predicted)
• 密度：
  0.94±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.0
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  38.33
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-溴丙烯 、 (4S,5R)-5-(1-methylpropa-1,2-dienyl)-4-(tert-butyldimethylsilyloxy)pyrrolidin-2-one 在 双(乙腈)氯化钯(II) potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以43%的产率得到(1S,7aR)-6-allyl-1-(tert-butyldimethylsilyloxy)-7-methyl-1,2,5,7a-tetrahydropyrrolizin-3-one
  参考文献：
  名称：

  N -Acyliminium ion chemistry and palladium catalysis: a useful combination to obtain bicyclic heterocycles

  摘要：

  By using N-acyliminium ion chemistry, several omega -propadienyllactams and a propadienyloxazolidine were prepared from N-acyliminium ion precursors and propargylsilanes. Treatment of these allene containing lactams and oxazolidinone with allyl halides or an allyl carbonate using Pd(II)-salts as the catalyst gave rise to a coupling-cyclization reaction, yielding bicyclic systems in which the allyl moiety is incorporated. With this methodology several substituted pyrrolizinones, an oxazolone and indolizinone were prepared. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00364-7
• 作为产物：
  描述：

  (4S,5R)-4-acetoxy-5-(1-methylpropa-1,2-dienyl)pyrrolidin-2-one 在 咪唑 、 4-二甲氨基吡啶 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.0h， 生成 (4S,5R)-5-(1-methylpropa-1,2-dienyl)-4-(tert-butyldimethylsilyloxy)pyrrolidin-2-one
  参考文献：
  名称：

  N -Acyliminium ion chemistry and palladium catalysis: a useful combination to obtain bicyclic heterocycles

  摘要：

  By using N-acyliminium ion chemistry, several omega -propadienyllactams and a propadienyloxazolidine were prepared from N-acyliminium ion precursors and propargylsilanes. Treatment of these allene containing lactams and oxazolidinone with allyl halides or an allyl carbonate using Pd(II)-salts as the catalyst gave rise to a coupling-cyclization reaction, yielding bicyclic systems in which the allyl moiety is incorporated. With this methodology several substituted pyrrolizinones, an oxazolone and indolizinone were prepared. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00364-7