tert-butyl N-[(1S)-1-[(3aS,6aR)-4,6a-dihydro-3aH-cyclopenta[d][1,3]oxazol-2-yl]ethyl]carbamate | 172487-60-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: tert-butyl N-[(1S)-1-[(3aS,6aR)-4,6a-dihydro-3aH-cyclopenta[d][1,3]oxazol-2-yl]ethyl]carbamate
• CAS: 172487-60-4
• 化学式: C₁₃H₂₀N₂O₃
• 分子量: 252.313
• InChiKey: GPYHLHOCZQQWKE-LPEHRKFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  59.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(1S)-1-[(3aS,6aR)-4,6a-dihydro-3aH-cyclopenta[d][1,3]oxazol-2-yl]ethyl]carbamate 在 盐酸 作用下， 以 水 为溶剂， 以67%的产率得到[(S)-1-((1S,2R)-2-Hydroxy-cyclopent-3-enylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Oxazoline formation via a palladium-catalyzed cyclization: A direct, stereoselective approach to cis-5-amino-2-cyclopenten-1-ol derivatives

  摘要：

  Alanyl substituted 4-amino-2-cyclopenten-1-yl acetates were obtained optically pure in three steps from cyclopentadiene. The Pd-0 catalyzed cyclization of these allylic acetates was studied using protected and unprotected derivatives. A novel oxazoline synthesis was developed and its utility was demonstrated by the preparation of a cis-5-amino-2-cyclopenten-1-ol derivative.

  DOI：

  10.1016/0040-4039(95)00465-o
• 作为产物：
  描述：

  (1R,4S)-N--2,3-oxazabicyclo<2.2.1>hept-5-ene 在 四(三苯基膦)钯 吡啶 、 hexacarbonyl molybdenum 、 sodium hydride 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 3.17h， 生成 tert-butyl N-[(1S)-1-[(3aS,6aR)-4,6a-dihydro-3aH-cyclopenta[d][1,3]oxazol-2-yl]ethyl]carbamate
  参考文献：
  名称：

  Synthesis of enantiomerically pure 5'-aza-noraristeromycin analogs

  摘要：

  The synthesis of a novel class of enantiomerically pure azanoraristeromycins is described. An asymmetric hetero Diels-Alder reaction using amino acid-derived chiral acylnitroso dienophiles 2 was used to prepare optically pure allylic acetate substrate 10. The palladium(0)-catalyzed addition of the sodium salt of adenine to optically pure acetate 10 was achieved to give N-9-alkylated adenine adduct 11 in good yield. Catalytic osmium tetraoxide dihydroxylation of the didehydro analog provided both diol products 17 and 18, corresponding to common natural and unnatural nucleosides, respectively.

  DOI：

  10.1021/jo00123a015