(S)-2,2,2-trichloroethyl 4-[(4-hydroxyphenyl)methyl]-2,2-dimethyl-3-oxazolidinecarboxylate | 1202810-30-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (S)-2,2,2-trichloroethyl 4-[(4-hydroxyphenyl)methyl]-2,2-dimethyl-3-oxazolidinecarboxylate
• CAS: 1202810-30-7
• 化学式: C₁₅H₁₈Cl₃NO₄
• 分子量: 382.671
• InChiKey: IYWAIIHEYVZQRP-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.88
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  59.0
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (S)-2,2,2-trichloroethyl 4-[(4-hydroxyphenyl)methyl]-2,2-dimethyl-3-oxazolidinecarboxylate 在 碘苯二乙酸 、 水 作用下， 以 丙酮 为溶剂， 以52%的产率得到(S)-2,2,2-trichloroethyl 4-[(1-hydroxy-4-oxo-2,5-cyclohexadien-1-yl)methyl]-2,2-dimethyl-3-oxazolidinecarboxylate
  参考文献：
  名称：

  Dynamic Kinetic Resolution During a Vinylogous Payne Rearrangement: A Concise Synthesis of the Polar Pharmacophoric Subunit of (+)-Scyphostatin

  摘要：

  The diastereomeric epoxycyclohexenols 3a/b (obtained via a Wharton rearrangement of a bis-epoxycyclohexanone precursor) were shown to undergo interconversion via a facile vinylogous Payne rearrangement. Mechanistic issues were probed; the doubly O-deuterated analogues underwent this equilibration more slowly than the parent dihydroxy compounds. It was possible to kinetically resolve the mixture of 3a/b under equilibrating conditions by use of Amano PS. This DKR is additionally noteworthy because it sets four stereocenters in a single event.

  DOI：

  10.1021/ol902459z
• 作为产物：
  描述：

  Troc-tyrosinol 、 2,2-二甲氧基丙烷 在 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 反应 5.0h， 以373.7 mg的产率得到(S)-2,2,2-trichloroethyl 4-[(4-hydroxyphenyl)methyl]-2,2-dimethyl-3-oxazolidinecarboxylate
  参考文献：
  名称：

  Dynamic Kinetic Resolution During a Vinylogous Payne Rearrangement: A Concise Synthesis of the Polar Pharmacophoric Subunit of (+)-Scyphostatin

  摘要：

  The diastereomeric epoxycyclohexenols 3a/b (obtained via a Wharton rearrangement of a bis-epoxycyclohexanone precursor) were shown to undergo interconversion via a facile vinylogous Payne rearrangement. Mechanistic issues were probed; the doubly O-deuterated analogues underwent this equilibration more slowly than the parent dihydroxy compounds. It was possible to kinetically resolve the mixture of 3a/b under equilibrating conditions by use of Amano PS. This DKR is additionally noteworthy because it sets four stereocenters in a single event.

  DOI：

  10.1021/ol902459z