(rac)-(4aSR,7aRS)-hexahydrocyclopenta[d][1,3]oxazin-2-one | 5687-61-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: (rac)-(4aSR,7aRS)-hexahydrocyclopenta[d][1,3]oxazin-2-one
• 英文别名: (rac)-(4aS,7aR)-hexahydrocyclopenta[d][1,3]oxazin-2-one；(4ar,7ac)-hexahydro-cyclopenta[d][1,3]oxazin-2-one；2-Oxa-4-aza-bicyclo<4.3.0>nonanon-(3)；(4aR,7aS)-4,4a,5,6,7,7a-hexahydro-1H-cyclopenta[d][1,3]oxazin-2-one
• CAS: 5687-61-6
• 化学式: C₇H₁₁NO₂
• 分子量: 141.17
• InChiKey: WPBUYFXDPRXMRX-WDSKDSINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (rac)-(4aSR,7aRS)-hexahydrocyclopenta[d][1,3]oxazin-2-one 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 cis-N-methyl-2-hydroxymethylcyclopentylamine
  参考文献：
  名称：

  Amine Oxides. VII. The Thermal Decomposition of the N-Oxides of N-Methylazacycloalkanes^1,2

  摘要：

  Ring cleavage of the N-oxides of N-methylazacycloalkanes by a thermal elimination reaction does not occur when the ring is six-membered and becontes progressively easier as the ring size is increased from seven to eight atoms. N-Methylpiperidine oxide gave no product from a cis beta-elimination reaction, while pyrolysis of the homologous N-methylhexamethyleneimine and N-methylheptamethyleneimine oxides led to the unsaturated hydroxylamines in yields of 53 and 79%, respectively. These results support a planar five-membered transition state for the amine oxide pyrolysis. The unsaturated hydroxylamines were converted to unsaturated and saturated secondary amines. The thermal decomposition of a mixture of he cis and trans isomers of N-methyl-alpha-pipecoline oxide formed the expected N-methyl-N-5-hexenylhydroxylamine as well as a saturated bicyclic product, formulated as cis-N-methyl-3-oxa-2-azabicyclo [3.3.01 octane. A possible mechanism for the formation of this product is presented. The cis and trans isomers of N-methyl-a-pipecoline oxide have been separated and characterized. Each Of the isomers has been pyrolyzed separately and only trans-N-methyl-a-pipecoline oxide formed the expected unsaturated hydroxylamine.

  DOI：

  10.1021/ja01502a052
• 作为产物：
  描述：

  hexahydro-cyclopenta[c]furan-1-one 在 肼 作用下， 反应 2.0h， 生成 (rac)-(4aSR,7aRS)-hexahydrocyclopenta[d][1,3]oxazin-2-one
  参考文献：
  名称：

  Amine Oxides. VII. The Thermal Decomposition of the N-Oxides of N-Methylazacycloalkanes^1,2

  摘要：

  Ring cleavage of the N-oxides of N-methylazacycloalkanes by a thermal elimination reaction does not occur when the ring is six-membered and becontes progressively easier as the ring size is increased from seven to eight atoms. N-Methylpiperidine oxide gave no product from a cis beta-elimination reaction, while pyrolysis of the homologous N-methylhexamethyleneimine and N-methylheptamethyleneimine oxides led to the unsaturated hydroxylamines in yields of 53 and 79%, respectively. These results support a planar five-membered transition state for the amine oxide pyrolysis. The unsaturated hydroxylamines were converted to unsaturated and saturated secondary amines. The thermal decomposition of a mixture of he cis and trans isomers of N-methyl-alpha-pipecoline oxide formed the expected N-methyl-N-5-hexenylhydroxylamine as well as a saturated bicyclic product, formulated as cis-N-methyl-3-oxa-2-azabicyclo [3.3.01 octane. A possible mechanism for the formation of this product is presented. The cis and trans isomers of N-methyl-a-pipecoline oxide have been separated and characterized. Each Of the isomers has been pyrolyzed separately and only trans-N-methyl-a-pipecoline oxide formed the expected unsaturated hydroxylamine.

  DOI：

  10.1021/ja01502a052