(S)-2,2,2-trichloroethyl 4-(((1R,2s,3S,5R,7S)-2-hydroxy-6-oxo-4,8-dioxatricyclo[5.1.0.0(3,5)]octan-2-yl)methyl)-2,2-dimethyloxazolidine-3-carboxylate | 1202810-29-4

• 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: (S)-2,2,2-trichloroethyl 4-(((1R,2s,3S,5R,7S)-2-hydroxy-6-oxo-4,8-dioxatricyclo[5.1.0.0(3,5)]octan-2-yl)methyl)-2,2-dimethyloxazolidine-3-carboxylate
• CAS: 1202810-29-4
• 化学式: C₁₅H₁₈Cl₃NO₇
• 分子量: 430.669
• InChiKey: RPIWXOFDKVAHCL-DVNWFODESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.17
• 重原子数：
  26.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  101.13
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (S)-2,2,2-trichloroethyl 4-(((1R,2s,3S,5R,7S)-2-hydroxy-6-oxo-4,8-dioxatricyclo[5.1.0.0(3,5)]octan-2-yl)methyl)-2,2-dimethyloxazolidine-3-carboxylate 在 一水合肼 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 0.25h， 生成 (S)-2,2,2-trichloroethyl 4-(((1S,2R,3R,6S)-2,3-dihydroxy-7-oxabicyclo[4.1.0]hept-4-en-2-yl)methyl)-2,2-dimethyloxazolidine-3-carboxylate 、 (S)-2,2,2-trichloroethyl 4-(((1R,2S,3S,6R)-2,3-dihydroxy-7-oxabicyclo[4.1.0]hept-4-en-2-yl)methyl)-2,2-dimethyloxazolidine-3-carboxylate
  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：

  (S)-2,2,2-trichloroethyl 4-[(1-hydroxy-4-oxo-2,5-cyclohexadien-1-yl)methyl]-2,2-dimethyl-3-oxazolidinecarboxylate 在 水 、 双氧水 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 16.0h， 生成 (S)-2,2,2-trichloroethyl 4-(((1R,2s,3S,5R,7S)-2-hydroxy-6-oxo-4,8-dioxatricyclo[5.1.0.0(3,5)]octan-2-yl)methyl)-2,2-dimethyloxazolidine-3-carboxylate
  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