(2'E,4R,5S)-4-Methyl-5-phenyl-3-(4',4',4'-trifluoro-3'-methylbut-2-enoyl)oxazolidin-2-one | 162788-67-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (2'E,4R,5S)-4-Methyl-5-phenyl-3-(4',4',4'-trifluoro-3'-methylbut-2-enoyl)oxazolidin-2-one
• 英文别名: (4R,5S)-4-methyl-5-phenyl-3-[(E)-4,4,4-trifluoro-3-methylbut-2-enoyl]-1,3-oxazolidin-2-one
• CAS: 162788-67-2
• 化学式: C₁₅H₁₄F₃NO₃
• 分子量: 313.276
• InChiKey: HXNUFYZXDFLIEE-NNWFXZMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2'E,4R,5S)-4-Methyl-5-phenyl-3-(4',4',4'-trifluoro-3'-methylbut-2-enoyl)oxazolidin-2-one 在 camphor-10-sulfonic acid 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 (4S,5S)-4-<(1,2-Dihydro-4-methoxybenzocyclobuten-1-yl)methyl>-2,2-dimethyl-5-<1-(trifluoromethyl)vinyl>-1,3-dioxane
  参考文献：
  名称：

  A Rapid Access to Both Enantiomers of 1,2,3,4-Tetranor B-Trienic 18,18,18-Trifluorosteroids. The First Enantiocontrolled Total Synthesis of 18,18,18-Trifluorosteroids

  摘要：

  Chiral A-tetranor B-trienic 18,18,18-trifluorosteroid 2a and its enantiomer 1a were synthesised by the thermolysis of chiral olefinic benzocyclobutenes 7b and 7a which were in turn prepared by the aldol reaction of chiral oxazolidinone 5 and 11 with 2-(4-methoxybenzocyclobutenyl-1)-acetaldehyde as a key step. The compound 1a was then transformed into 18,18,18-trifluorosteroid 9 via the ketone 13 and the diketone 14.

  DOI：

  10.1021/jo00108a022
• 作为产物：
  描述：

  (E)-3-三氟甲基-2-丁烯酸乙酯 在 lithium hydroxide 、 正丁基锂 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 10.5h， 生成 (2'E,4R,5S)-4-Methyl-5-phenyl-3-(4',4',4'-trifluoro-3'-methylbut-2-enoyl)oxazolidin-2-one
  参考文献：
  名称：

  A Rapid Access to Both Enantiomers of 1,2,3,4-Tetranor B-Trienic 18,18,18-Trifluorosteroids. The First Enantiocontrolled Total Synthesis of 18,18,18-Trifluorosteroids

  摘要：

  Chiral A-tetranor B-trienic 18,18,18-trifluorosteroid 2a and its enantiomer 1a were synthesised by the thermolysis of chiral olefinic benzocyclobutenes 7b and 7a which were in turn prepared by the aldol reaction of chiral oxazolidinone 5 and 11 with 2-(4-methoxybenzocyclobutenyl-1)-acetaldehyde as a key step. The compound 1a was then transformed into 18,18,18-trifluorosteroid 9 via the ketone 13 and the diketone 14.

  DOI：

  10.1021/jo00108a022

文献信息

• A Rapid Access to Both Enantiomers of 1,2,3,4-Tetranor B-Trienic 18,18,18-Trifluorosteroids. The First Enantiocontrolled Total Synthesis of 18,18,18-Trifluorosteroids
  作者：Hideo Nemoto、Atsushi Satoh、Keiichiro Fukumoto、Chizuko Kabuto

  DOI：10.1021/jo00108a022

  日期：1995.2

  Chiral A-tetranor B-trienic 18,18,18-trifluorosteroid 2a and its enantiomer 1a were synthesised by the thermolysis of chiral olefinic benzocyclobutenes 7b and 7a which were in turn prepared by the aldol reaction of chiral oxazolidinone 5 and 11 with 2-(4-methoxybenzocyclobutenyl-1)-acetaldehyde as a key step. The compound 1a was then transformed into 18,18,18-trifluorosteroid 9 via the ketone 13 and the diketone 14.