(R)-1-((S)-1-phenylethyl)-4-(((triisopropylsilyl)oxy)methyl)pyrrolidin-2-one | 1580503-39-4

• 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: (R)-1-((S)-1-phenylethyl)-4-(((triisopropylsilyl)oxy)methyl)pyrrolidin-2-one
• CAS: 1580503-39-4
• 化学式: C₂₂H₃₇NO₂Si
• 分子量: 375.627
• InChiKey: TYNBEITXECLIJW-VQTJNVASSA-N

物化性质

• 沸点：
  453.9±28.0 °C(predicted)
• 密度：
  0.976±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.79
• 重原子数：
  26.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (R)-1-((S)-1-phenylethyl)-4-(((triisopropylsilyl)oxy)methyl)pyrrolidin-2-one 在 2,2,6,6-四甲基哌啶 、 正丁基锂 、 叠氮磷酸二苯酯 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 11.92h， 生成 tert-butyl ((3S,4S)-3-methyl-2-oxo-1-((S)-1-phenylethyl)-4-(((triisopropylsilyl)oxy)methyl)pyrrolidin-3-yl)carbamate
  参考文献：
  名称：

  Synthesis of a cyclic isostere of α-methyl homoserine by a stereoselective acylation–alkylation sequence of a chiral γ-lactam

  摘要：

  Starting from a chiral 4-hydroxymethyl pyrrolidin-2-one, an isostere of alpha-methyl homoserine tethered on a gamma-lactam ring was prepared exploiting a stereoselective acylation-methylation sequence, followed by Curtius rearrangement, and structural assignment was confirmed by n.O.e. experiments. By reverting the sequence, the 3-carboxy-3-methyl derivative having the opposite configuration at C-3 was obtained with total stereoselection, but Curtius rearrangement invariably afforded only inseparable mixtures of decomposition products.

  DOI：

  10.1007/s00726-014-1671-9
• 作为产物：
  描述：

  三异丙基氯硅烷 、 (4R,1'S)-4-hydroxymethyl-1-(1'-phenylethyl)pyrrolidin-2-one 在 咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以72%的产率得到(R)-1-((S)-1-phenylethyl)-4-(((triisopropylsilyl)oxy)methyl)pyrrolidin-2-one
  参考文献：
  名称：

  Synthesis of a cyclic isostere of α-methyl homoserine by a stereoselective acylation–alkylation sequence of a chiral γ-lactam

  摘要：

  Starting from a chiral 4-hydroxymethyl pyrrolidin-2-one, an isostere of alpha-methyl homoserine tethered on a gamma-lactam ring was prepared exploiting a stereoselective acylation-methylation sequence, followed by Curtius rearrangement, and structural assignment was confirmed by n.O.e. experiments. By reverting the sequence, the 3-carboxy-3-methyl derivative having the opposite configuration at C-3 was obtained with total stereoselection, but Curtius rearrangement invariably afforded only inseparable mixtures of decomposition products.

  DOI：

  10.1007/s00726-014-1671-9