(3R)-1-cyanomethyl-3-isobutyl-3-[(4S)-4-phenyl-2-oxo-1,3-oxazolidin-3-yl]azetidin-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (3R)-1-cyanomethyl-3-isobutyl-3-[(4S)-4-phenyl-2-oxo-1,3-oxazolidin-3-yl]azetidin-2-one
• 英文别名: 2-[(3R)-3-(2-methylpropyl)-2-oxo-3-[(4S)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl]azetidin-1-yl]acetonitrile
• 化学式: C₁₈H₂₁N₃O₃
• 分子量: 327.383
• InChiKey: PPZATAFYSXEJPW-CRAIPNDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  73.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  三甲基硅基异氰酸酯 、 (3R)-1-[bis(trimethylsilyl)methyl]-3-(3-methylpropyl)-3-[(4S)-2-oxo-4-phenyloxazolidin-3-yl]azetidin-2-one 在 正丁基锂 、 四甲基乙二胺 作用下， 以 四氢呋喃 为溶剂， 反应 5.5h， 以60%的产率得到(3R)-1-cyanomethyl-3-isobutyl-3-[(4S)-4-phenyl-2-oxo-1,3-oxazolidin-3-yl]azetidin-2-one
  参考文献：
  名称：

  Functionalization of N-[(Silyl)methyl]-β-lactam Carbanions with Carbon Electrophiles

  摘要：

  Latent acidity of alpha-alkyl-alpha-amino-N-[(silyl) methyl]-beta-lactams enabled a concise entry to lithium nonenolate N-methyl-azetidinone carbanions lithiated alpha' to the beta-lactam nitrogen, owing to the stabilizing "alpha-effect" of one or two trimethylsilyl groups. (BuLi)-Bu-n/TMEDA and 'BuLi/TMEDA were the bases of choice for complete deprotonation of di- and monosilylated beta-lactams, respectively. Trapping of the resulting carbanions with alkyl halides provided the corresponding N-[(alpha'-silyl)-alkyl]-beta-lactams, while carbon dioxide and related electrophiles such as benzyl chloroformates or isocyanates, afforded the corresponding silicon-free N-carboxymethyl-, N-benzyloxycarbonylmethyl-, and N-amidomethyl-beta-lactams in a single synthetic step. Likely structures of these unprecedented lithiated N-[(silyl) methyl]-beta-lactams were studied by MO calculations (B3LYP/6-31G*), and the origin of their relative stability was briefly discussed.

  DOI：

  10.1021/jo060537g

文献信息

• Functionalization of <i>N</i>-[(Silyl)methyl]-β-lactam Carbanions with Carbon Electrophiles
  作者：Claudio Palomo、Jesus M. Aizpurua、Ana Benito、Lourdes Cuerdo、Raluca M. Fratila、José I. Miranda、Anthony Linden

  DOI：10.1021/jo060537g

  日期：2006.8.1

  Latent acidity of alpha-alkyl-alpha-amino-N-[(silyl) methyl]-beta-lactams enabled a concise entry to lithium nonenolate N-methyl-azetidinone carbanions lithiated alpha' to the beta-lactam nitrogen, owing to the stabilizing "alpha-effect" of one or two trimethylsilyl groups. (BuLi)-Bu-n/TMEDA and 'BuLi/TMEDA were the bases of choice for complete deprotonation of di- and monosilylated beta-lactams, respectively. Trapping of the resulting carbanions with alkyl halides provided the corresponding N-[(alpha'-silyl)-alkyl]-beta-lactams, while carbon dioxide and related electrophiles such as benzyl chloroformates or isocyanates, afforded the corresponding silicon-free N-carboxymethyl-, N-benzyloxycarbonylmethyl-, and N-amidomethyl-beta-lactams in a single synthetic step. Likely structures of these unprecedented lithiated N-[(silyl) methyl]-beta-lactams were studied by MO calculations (B3LYP/6-31G*), and the origin of their relative stability was briefly discussed.