trans-3(S)-Amino-1-<(R)-(1,4-cyclohexadienyl)(methoxycarbonyl)methyl>-4(S)-phenyl-2-azetidinone | 164122-60-5

• 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: trans-3(S)-Amino-1-<(R)-(1,4-cyclohexadienyl)(methoxycarbonyl)methyl>-4(S)-phenyl-2-azetidinone
• 英文别名: methyl (2R)-2-[(3S,4S)-3-amino-2-oxo-4-phenylazetidin-1-yl]-2-cyclohexa-1,4-dien-1-ylacetate
• CAS: 164122-60-5
• 化学式: C₁₈H₂₀N₂O₃
• 分子量: 312.368
• InChiKey: UVSKUPGZHCJMAU-HRCADAONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  72.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  苯酐 、 trans-3(S)-Amino-1-<(R)-(1,4-cyclohexadienyl)(methoxycarbonyl)methyl>-4(S)-phenyl-2-azetidinone 以 苯 为溶剂， 反应 16.0h， 生成 trans-1-<(R)-(1,4-Cyclohexadienyl)(methoxycarbonyl)methyl>-4(S)-phenyl-(S)-phthalimido-2-azetidinone
  参考文献：
  名称：

  Asymmetric Synthesis of .beta.-Lactams via the Zinc-Mediated Glycine Ester Enolate-Imine Condensation Reaction Using .alpha.-Amino Esters as the Chiral Auxiliary

  摘要：

  Imine esters of glycine, (R)-phenylglycine, (R)-(1,4-cyclohexadienyl)glycine and (S)-valine have been employed in the ester enolate-imine condensation via double activation with ZnCl2. The reaction of the chlorozinc enolate (1b) of ethyl (2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopentyl)acetate with (R)-methyl N-benzylidene-2-phenylglycinate (2a) afforded the trans-beta-lactam 3a in 79% yield with excellent asymmetric induction (de >97%). Other imine esters also afforded trans-beta-lactams diastereoselectively, albeit in lower conversions (37-70%). Methyl (S)-2-[N-[3-(trimethylsilyl)-2-propyn-1-ylidene]amino]-3-methylbutanoate (2e) afforded a mixture of four diastereoisomers (68% conversion). The products were isolated as 3-phthalimido beta-lactams 5b-e and as 3-[(methoxycarbonyl)amino]-beta-lactam 6b. The reactivity of the zinc enolates and the diastereoselectivity of the reactions are discussed in terms of the coordination of the imine esters to ZnCl2 (template effect) and the stability and aggregation equilibria of the zinc enolates.

  DOI：

  10.1021/jo00119a009
• 作为产物：
  描述：

  trans-1-<(R)-(1,4-Cyclohexadienyl)(methoxycarbonyl)methyl>-3-(S)-(2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopentyl)-4(S)-phenyl-2-azetidinone 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 trans-3(S)-Amino-1-<(R)-(1,4-cyclohexadienyl)(methoxycarbonyl)methyl>-4(S)-phenyl-2-azetidinone
  参考文献：
  名称：

  Asymmetric Synthesis of .beta.-Lactams via the Zinc-Mediated Glycine Ester Enolate-Imine Condensation Reaction Using .alpha.-Amino Esters as the Chiral Auxiliary

  摘要：

  Imine esters of glycine, (R)-phenylglycine, (R)-(1,4-cyclohexadienyl)glycine and (S)-valine have been employed in the ester enolate-imine condensation via double activation with ZnCl2. The reaction of the chlorozinc enolate (1b) of ethyl (2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopentyl)acetate with (R)-methyl N-benzylidene-2-phenylglycinate (2a) afforded the trans-beta-lactam 3a in 79% yield with excellent asymmetric induction (de >97%). Other imine esters also afforded trans-beta-lactams diastereoselectively, albeit in lower conversions (37-70%). Methyl (S)-2-[N-[3-(trimethylsilyl)-2-propyn-1-ylidene]amino]-3-methylbutanoate (2e) afforded a mixture of four diastereoisomers (68% conversion). The products were isolated as 3-phthalimido beta-lactams 5b-e and as 3-[(methoxycarbonyl)amino]-beta-lactam 6b. The reactivity of the zinc enolates and the diastereoselectivity of the reactions are discussed in terms of the coordination of the imine esters to ZnCl2 (template effect) and the stability and aggregation equilibria of the zinc enolates.

  DOI：

  10.1021/jo00119a009

文献信息

• Asymmetric Synthesis of .beta.-Lactams via the Zinc-Mediated Glycine Ester Enolate-Imine Condensation Reaction Using .alpha.-Amino Esters as the Chiral Auxiliary
  作者：Hendrik L. van Maanen、Henk Kleijn、Johann T. B. H. Jastrzebski、Jan Verweij、Antonius P. G. Kieboom、Gerard van Koten

  DOI：10.1021/jo00119a009

  日期：1995.7

  Imine esters of glycine, (R)-phenylglycine, (R)-(1,4-cyclohexadienyl)glycine and (S)-valine have been employed in the ester enolate-imine condensation via double activation with ZnCl2. The reaction of the chlorozinc enolate (1b) of ethyl (2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopentyl)acetate with (R)-methyl N-benzylidene-2-phenylglycinate (2a) afforded the trans-beta-lactam 3a in 79% yield with excellent asymmetric induction (de >97%). Other imine esters also afforded trans-beta-lactams diastereoselectively, albeit in lower conversions (37-70%). Methyl (S)-2-[N-[3-(trimethylsilyl)-2-propyn-1-ylidene]amino]-3-methylbutanoate (2e) afforded a mixture of four diastereoisomers (68% conversion). The products were isolated as 3-phthalimido beta-lactams 5b-e and as 3-[(methoxycarbonyl)amino]-beta-lactam 6b. The reactivity of the zinc enolates and the diastereoselectivity of the reactions are discussed in terms of the coordination of the imine esters to ZnCl2 (template effect) and the stability and aggregation equilibria of the zinc enolates.