tert-butyl (4aR,5R,7aR)-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-hydroxyhexahydrocyclopenta[d][1,2]oxazine-3(1H)-carboxylate | 569349-94-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂螺癸烷衍生物
• 英文名称: tert-butyl (4aR,5R,7aR)-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-hydroxyhexahydrocyclopenta[d][1,2]oxazine-3(1H)-carboxylate
• CAS: 569349-94-6
• 化学式: C₁₇H₂₉NO₆
• 分子量: 343.42
• InChiKey: QIMKKTKZWRDBQS-HTFWJNBQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.93
• 重原子数：
  24.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  77.46
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (4aR,5R,7aR)-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-hydroxyhexahydrocyclopenta[d][1,2]oxazine-3(1H)-carboxylate 在 disodium hydrogenphosphate 、 sodium amalgam 作用下， 以 乙醇 为溶剂， 反应 8.0h， 以77%的产率得到tert-butyl [(1R,2R,5R)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-5-(hydroxymethyl)cyclopentyl]methylcarbamate
  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-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