Benzyl 7,7-dichloro-6-oxo-2-azabicyclo[3.2.0]heptane-2-carboxylate | 147369-09-3

• 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: Benzyl 7,7-dichloro-6-oxo-2-azabicyclo[3.2.0]heptane-2-carboxylate
• CAS: 147369-09-3
• 化学式: C₁₄H₁₃Cl₂NO₃
• 分子量: 314.168
• InChiKey: RUJPIWFIOLDCNB-UHFFFAOYSA-N

物化性质

• 沸点：
  464.9±45.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Benzyl 7,7-dichloro-6-oxo-2-azabicyclo[3.2.0]heptane-2-carboxylate 在 溶剂黄146 、 锌 作用下， 以82%的产率得到benzyl 3-acetylpyrrolidine-1-carboxylate
  参考文献：
  名称：

  Microbial Baeyer–Villiger oxidation applied to the synthesis of the N-protected (1R,5R)-Geisman–Waiss lactone

  摘要：

  Using whole cell Baeyer-Villiger biooxidation as a key step and depending on the choice of the biocatalyst {E. coli TOP10[pQR239] or Acinetobacter TD63}, the synthesis of nearly enantiopure N-protected (1R,5R)-(-)-Geisman-Waiss lactone (92% ee) or its (1R,5S)-(-) regioisomer (98% ee) be performed. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.06.038
• 作为产物：
  描述：

  N-Cbz-3-羟基吡咯烷 在 三乙胺 作用下， 以 甲苯 为溶剂， 生成 Benzyl 7,7-dichloro-6-oxo-2-azabicyclo[3.2.0]heptane-2-carboxylate
  参考文献：
  名称：

  Microbial Baeyer–Villiger oxidation applied to the synthesis of the N-protected (1R,5R)-Geisman–Waiss lactone

  摘要：

  Using whole cell Baeyer-Villiger biooxidation as a key step and depending on the choice of the biocatalyst {E. coli TOP10[pQR239] or Acinetobacter TD63}, the synthesis of nearly enantiopure N-protected (1R,5R)-(-)-Geisman-Waiss lactone (92% ee) or its (1R,5S)-(-) regioisomer (98% ee) be performed. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.06.038

文献信息

• [2+2] Cycloaddition reaction of cyclic enecarbamates and enamides with ketenes. A short and efficient synthesis of the Geissman-Waiss lactone.
  作者：Antônio R. de Faria、Carlos Roberto R. Matos、Carlos Roque D. Correia

  DOI：10.1016/s0040-4039(00)60049-7

  日期：1993.1

  The synthesis of several 2-aza-bicyclo[3.2.0] heptan-6-ones has been achieved in a regiospecific manner through a [2+2] cycloaddition reaction between

  通过[2 + 2]环加成反应之间的区域专一性，已经实现了几种2-氮杂-双环[3.2.0]庚烷-6-酮的合成。
• Microbial Baeyer–Villiger oxidation applied to the synthesis of the N-protected (1R,5R)-Geisman–Waiss lactone
  作者：Amparo Luna、Maria-Concepcion Gutiérrez、Roland Furstoss、Véronique Alphand

  DOI：10.1016/j.tetasy.2005.06.038

  日期：2005.8

  Using whole cell Baeyer-Villiger biooxidation as a key step and depending on the choice of the biocatalyst E. coli TOP10[pQR239] or Acinetobacter TD63}, the synthesis of nearly enantiopure N-protected (1R,5R)-(-)-Geisman-Waiss lactone (92% ee) or its (1R,5S)-(-) regioisomer (98% ee) be performed. (c) 2005 Elsevier Ltd. All rights reserved.