tert-butyl 5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-oxohexahydrocyclopenta[d][1,2]oxazine-3(1H)-carboxylate | 569349-93-5

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: tert-butyl 5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-oxohexahydrocyclopenta[d][1,2]oxazine-3(1H)-carboxylate
• 英文别名: tert-butyl (4aR,5S,7aR)-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-oxo-1,4,4a,5,7,7a-hexahydrocyclopenta[d]oxazine-3-carboxylate
• CAS: 569349-93-5
• 化学式: C₁₇H₂₇NO₆
• 分子量: 341.404
• InChiKey: OAWRRDMAXUIHNK-OIMNJJJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  74.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl 5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-oxohexahydrocyclopenta[d][1,2]oxazine-3(1H)-carboxylate 在 锂硼氢 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以80%的产率得到tert-butyl (4aR,5R,7aR)-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-hydroxyhexahydrocyclopenta[d][1,2]oxazine-3(1H)-carboxylate
  参考文献：
  名称：

  A Transient N−O-Linked Pauson−Khand Strategy for the Synthesis of the Deschloro Carbocyclic Core of the Palau'amines and Styloguanidines

  摘要：

  A stereocontrolled route to the deschloro cyclopentyl core of the palau'amines and styloguanidines has been developed. This strategy makes use of the intramolecular Pauson-Khand cyclization of an enyne with a "transient N-O tether" to construct a five-membered carbocycle in a diastereoselective fashion.

  DOI：

  10.1021/ol0344063
• 作为产物：
  描述：

  tert-butyl 5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-oxo-4,4a,5,6-tetrahydrocyclopenta[d][1,2]oxazine-3(1H)-carboxylate 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 10.0h， 以95%的产率得到tert-butyl 5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-oxohexahydrocyclopenta[d][1,2]oxazine-3(1H)-carboxylate
  参考文献：
  名称：

  A Transient N−O-Linked Pauson−Khand Strategy for the Synthesis of the Deschloro Carbocyclic Core of the Palau'amines and Styloguanidines

  摘要：

  A stereocontrolled route to the deschloro cyclopentyl core of the palau'amines and styloguanidines has been developed. This strategy makes use of the intramolecular Pauson-Khand cyclization of an enyne with a "transient N-O tether" to construct a five-membered carbocycle in a diastereoselective fashion.

  DOI：

  10.1021/ol0344063