cis,anti-3-<1'-(Dimethylphenylsilyl)ethyl>-4-(methoxycarbonyl)azetidin-2-one | 138235-13-9

• 英文名称: cis,anti-3-<1'-(Dimethylphenylsilyl)ethyl>-4-(methoxycarbonyl)azetidin-2-one
• 英文别名: cis,anti-3-[1'-(Dimethylphenylsilyl)ethyl]-4-(methoxycarbonyl)azetidin-2-one；methyl (2S,3S)-3-[(1R)-1-[dimethyl(phenyl)silyl]ethyl]-4-oxoazetidine-2-carboxylate
• CAS: 138235-13-9
• 化学式: C₁₅H₂₁NO₃Si
• 分子量: 291.422
• InChiKey: MJNCREAVOLGPQQ-WXHSDQCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.28
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  cis,anti-3-<1'-(Dimethylphenylsilyl)ethyl>-4-(methoxycarbonyl)azetidin-2-one 在 四氟硼酸-二乙醚络合物 、 三甲基氯硅烷 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 9.0h， 生成
  参考文献：
  名称：

  Formation of 3-[1'-(dimethylphenylsilyl)ethyl]azetidin-2-ones: stereocontrolled formal approach to (.+-.)-thienamycin and (.+-.)-.beta.-(hydroxyalkyl)aspartic acid derivatives

  摘要：

  Reaction between (+/-)-beta-(dimethylphenylsilyl)alkanoyl chlorides and imines of glyoxylic esters provided a route to (+/-)-cis-3-[1'-(dimethylphenylsilyl)ethyl]-4-alkoxycarbonyl beta-lactams, while addition of the Fleming's silylcuprate reagent to methyl crotonate and further enolate trapping by the above imines furnished the corresponding (+/-)-trans-3-[1'-(dimethylphenylsilyl)ethyl]-4-alkoxycarbonyl beta-lactams. These beta-lactams, upon appropriate chemical manipulations, provided a stereocontrolled route to (+/-)-thienamycin precursors and (+/-)-beta-(hydroxyalkyl)aspartic acid derivatives.

  DOI：

  10.1021/jo00031a044
• 作为产物：
  描述：

  methyl (2S,3S)-1-[bis(4-methoxyphenyl)methyl]-3-[(1R)-1-[dimethyl(phenyl)silyl]ethyl]-4-oxoazetidine-2-carboxylate 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 3.0h， 以80%的产率得到cis,anti-3-<1'-(Dimethylphenylsilyl)ethyl>-4-(methoxycarbonyl)azetidin-2-one
  参考文献：
  名称：

  Formation of 3-[1'-(dimethylphenylsilyl)ethyl]azetidin-2-ones: stereocontrolled formal approach to (.+-.)-thienamycin and (.+-.)-.beta.-(hydroxyalkyl)aspartic acid derivatives

  摘要：

  Reaction between (+/-)-beta-(dimethylphenylsilyl)alkanoyl chlorides and imines of glyoxylic esters provided a route to (+/-)-cis-3-[1'-(dimethylphenylsilyl)ethyl]-4-alkoxycarbonyl beta-lactams, while addition of the Fleming's silylcuprate reagent to methyl crotonate and further enolate trapping by the above imines furnished the corresponding (+/-)-trans-3-[1'-(dimethylphenylsilyl)ethyl]-4-alkoxycarbonyl beta-lactams. These beta-lactams, upon appropriate chemical manipulations, provided a stereocontrolled route to (+/-)-thienamycin precursors and (+/-)-beta-(hydroxyalkyl)aspartic acid derivatives.

  DOI：

  10.1021/jo00031a044