(3S,4S,1'S)-1-(1'-phenylethyl)-3-methyl-3-methoxycarbonyl-4-triisopropylsilyloxymethylpyrrolidin-2-one | 1580503-67-8

• 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: (3S,4S,1'S)-1-(1'-phenylethyl)-3-methyl-3-methoxycarbonyl-4-triisopropylsilyloxymethylpyrrolidin-2-one
• 英文别名: (3S,4S)-methyl 3-methyl-2-oxo-1-((S)-1-phenylethyl)-4-(((triisopropylsilyl)oxy)methyl)pyrrolidine-3-carboxylate
• CAS: 1580503-67-8
• 化学式: C₂₅H₄₁NO₄Si
• 分子量: 447.69
• InChiKey: XGLABSRPORPBSD-XTJBDQBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.58
• 重原子数：
  31.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  55.84
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (3S,4S,1'S)-1-(1'-phenylethyl)-3-methyl-3-methoxycarbonyl-4-triisopropylsilyloxymethylpyrrolidin-2-one 在 sodium hydroxide 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 3.0h， 以98%的产率得到(3S,4S)-3-methyl-2-oxo-1-((S)-1-phenylethyl)-4-(((triisopropylsilyl)oxy)methyl)pyrrolidine-3-carboxylic acid
  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 在 2,2,6,6-四甲基哌啶 、 咪唑 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 8.84h， 生成 (3S,4S,1'S)-1-(1'-phenylethyl)-3-methyl-3-methoxycarbonyl-4-triisopropylsilyloxymethylpyrrolidin-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