3,3-dimethyl-4-phenyl-6-spirocyclopentyltetrahydro-1,3-oxazinium dimethyl phosphate

• 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: 3,3-dimethyl-4-phenyl-6-spirocyclopentyltetrahydro-1,3-oxazinium dimethyl phosphate
• 化学式: C₂H₆O₄P*C₁₆H₂₄NO
• 分子量: 371.414
• InChiKey: ISZLGSWMUYTQFF-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  3.24
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  67.82
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3,3-dimethyl-4-phenyl-6-spirocyclopentyltetrahydro-1,3-oxazinium dimethyl phosphate 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 9.0h， 以20%的产率得到3-methyl-4-phenyl-6-spirocyclopentyltetrahydro-1,3-oxazine
  参考文献：
  名称：

  Ring-opening of Isoxazolidine Nucleus by Trimethyl Posphate Treatment: Formation of Tertiary Allylic Alcohols via Intermediate 1,3-Oxazinium Salts

  摘要：

  5,5-Disubstituted isoxazolidines undergo ring opening reaction, leading to tertiary allylic alcohols, by sequential treatment with trimethyl phosphate (TMP) and NaH. The reaction proceeds through sequence steps which involve an initial alkylation to isoxazolidinium intermediate, followed by ring expansion to tetrahydro-1,3-oxazine, further alkylation and a Hofmann-like elimination towards the final products promoted by NaH.

  DOI：

  10.3987/com-92-6239
• 作为产物：
  描述：

  亚甲基环戊烷 在 cathecol 作用下， 以 甲苯 为溶剂， 反应 216.5h， 生成 3,3-dimethyl-4-phenyl-6-spirocyclopentyltetrahydro-1,3-oxazinium dimethyl phosphate
  参考文献：
  名称：

  Ring-opening of Isoxazolidine Nucleus by Trimethyl Posphate Treatment: Formation of Tertiary Allylic Alcohols via Intermediate 1,3-Oxazinium Salts

  摘要：

  5,5-Disubstituted isoxazolidines undergo ring opening reaction, leading to tertiary allylic alcohols, by sequential treatment with trimethyl phosphate (TMP) and NaH. The reaction proceeds through sequence steps which involve an initial alkylation to isoxazolidinium intermediate, followed by ring expansion to tetrahydro-1,3-oxazine, further alkylation and a Hofmann-like elimination towards the final products promoted by NaH.

  DOI：

  10.3987/com-92-6239

文献信息

• Ring-opening of Isoxazolidine Nucleus by Trimethyl Posphate Treatment: Formation of Tertiary Allylic Alcohols via Intermediate 1,3-Oxazinium Salts
  作者：Ugo Chiacchio、Angelo Liguori、Giovanni Romeo、Giovanni Sindona、Nicola Uccella

  DOI：10.3987/com-92-6239

  日期：——

  5,5-Disubstituted isoxazolidines undergo ring opening reaction, leading to tertiary allylic alcohols, by sequential treatment with trimethyl phosphate (TMP) and NaH. The reaction proceeds through sequence steps which involve an initial alkylation to isoxazolidinium intermediate, followed by ring expansion to tetrahydro-1,3-oxazine, further alkylation and a Hofmann-like elimination towards the final products promoted by NaH.