(4S)-4-benzyl-3-(3-phenylselanylpropanoyl)-1,3-oxazolidin-2-one | 1226966-85-3

• 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: (4S)-4-benzyl-3-(3-phenylselanylpropanoyl)-1,3-oxazolidin-2-one
• CAS: 1226966-85-3
• 化学式: C₁₉H₁₉NO₃Se
• 分子量: 388.325
• InChiKey: HXYNIHCFRDJFSK-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.41
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  三氟甲磺酸二丁硼 、 (4S)-4-benzyl-3-(3-phenylselanylpropanoyl)-1,3-oxazolidin-2-one 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Enantioselective Synthesis of α-Methylene-β-hydroxy Carboxylic Acid Derivatives via a Diastereoselective Aldol/β-Elimination Sequence: Application to the C(15)−C(21) Fragment of Tedanolide C

  摘要：

  An enantioselective synthesis of alpha-methylene-beta-hydroxy carboxylic acid derivatives via a highly diastereoselective, one-pot syn-aldol and beta-elimination sequence utilizing the chiral beta-(phenylselenyl)propionyl imide 15 is described. This new method, which constitutes an alternative to the Baylis-Hillman reaction, has been applied to the synthesis of the C(15)-C(21) fragment of tedanolide C.

  DOI：

  10.1021/ol1006955
• 作为产物：
  描述：

  苯硒酚 、 (S)-3-acryloyl-4-benzyloxazolidin-2-one 以 四氢呋喃 、 乙醇 为溶剂， 以96%的产率得到(4S)-4-benzyl-3-(3-phenylselanylpropanoyl)-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Enantioselective Synthesis of α-Methylene-β-hydroxy Carboxylic Acid Derivatives via a Diastereoselective Aldol/β-Elimination Sequence: Application to the C(15)−C(21) Fragment of Tedanolide C

  摘要：

  An enantioselective synthesis of alpha-methylene-beta-hydroxy carboxylic acid derivatives via a highly diastereoselective, one-pot syn-aldol and beta-elimination sequence utilizing the chiral beta-(phenylselenyl)propionyl imide 15 is described. This new method, which constitutes an alternative to the Baylis-Hillman reaction, has been applied to the synthesis of the C(15)-C(21) fragment of tedanolide C.

  DOI：

  10.1021/ol1006955

文献信息

• Enantioselective Synthesis of α-Methylene-β-hydroxy Carboxylic Acid Derivatives via a Diastereoselective Aldol/β-Elimination Sequence: Application to the C(15)−C(21) Fragment of Tedanolide C
  作者：Roland Barth、William R. Roush

  DOI：10.1021/ol1006955

  日期：2010.5.21

  An enantioselective synthesis of alpha-methylene-beta-hydroxy carboxylic acid derivatives via a highly diastereoselective, one-pot syn-aldol and beta-elimination sequence utilizing the chiral beta-(phenylselenyl)propionyl imide 15 is described. This new method, which constitutes an alternative to the Baylis-Hillman reaction, has been applied to the synthesis of the C(15)-C(21) fragment of tedanolide C.