2-Methyl-3-p-tolyl-5,5-diphenylisoxazolidine | 151231-97-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-Methyl-3-p-tolyl-5,5-diphenylisoxazolidine
• 英文别名: 2-Methyl-3-(4-methylphenyl)-5,5-diphenyl-1,2-oxazolidine
• CAS: 151231-97-9
• 化学式: C₂₃H₂₃NO
• 分子量: 329.442
• InChiKey: ZQCGDVSDAABHER-UHFFFAOYSA-N

物化性质

• 沸点：
  456.8±55.0 °C(Predicted)
• 密度：
  1.105±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-Methyl-3-p-tolyl-5,5-diphenylisoxazolidine 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 8.5h， 生成 1,1-diphenyl-3-p-tolylpropen-1-ol
  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：

  1,1-二苯乙烯 、 (Z)-N-methyl-1-(p-tolyl)methanimine oxide 在 cathecol 作用下， 以 甲苯 为溶剂， 反应 96.0h， 以90%的产率得到2-Methyl-3-p-tolyl-5,5-diphenylisoxazolidine
  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 substituted isoxazolidines: one-pot synthesis of indenes
  作者：Francesco Casuscelli、Ugo Chiacchio、Angelo Liguori、Giovanni Romeo、Giovanni Sindona、Nicola Uccella

  DOI：10.1016/s0040-4020(01)81879-2

  日期：1993.6.4

  High yield conversion of 3,5,5-triarylisoxazolidines into indene derivatives has been achieved by 4 h refluxing in aq. H2SO4. The rearrangement pathway is interpretable on the basis of a ring-opening process where the crucial step is the protonation of the oxygen atom of the isoxazolidine nucleus. MNDO calculations performed on N,N,O-trimethylhydroxylamine chosen as model system support the proposed mechanism.