(S)-4-benzyl-3-((2R,3R)-3-hydroxy-2-methylpent-4-enoyl)-oxazolidin-2-one | 1354716-10-1

• 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: (S)-4-benzyl-3-((2R,3R)-3-hydroxy-2-methylpent-4-enoyl)-oxazolidin-2-one
• 英文别名: (4S)-4-benzyl-3-[(2R,3R)-3-hydroxy-2-methylpent-4-enoyl]-1,3-oxazolidin-2-one
• CAS: 1354716-10-1
• 化学式: C₁₆H₁₉NO₄
• 分子量: 289.331
• InChiKey: AUSTXZTZGUNXOD-KWCYVHTRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-4-benzyl-3-((2R,3R)-3-hydroxy-2-methylpent-4-enoyl)-oxazolidin-2-one 、 but-3-yn-2-yl benzoate 在 Hoveyda-Blechert second generation catalyst 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 14.0h， 以82%的产率得到(6R,7R,E)-8-((S)-4-benzyl-2-oxooxazolidin-3-yl)-6-hydroxy-7-methyl-3-methylene-8-oxooct-4-en-2-yl benzoate
  参考文献：
  名称：

  Alkene Metathesis Approach to β-Unsubstituted Anti-Allylic Alcohols and Their Use in Ene–Yne Metathesis

  摘要：

  The synthesis of beta-unsubstituted, anti-allylic alcohols using a catalytic Evans aldol reaction conjoined with a relay-type ring-closing alkene metathesis is reported. The metathesis step serves to remove a beta-alkenyl group, which facilitated the aldol step. The beta-substituted enals serve as acrolein surrogates. The products were employed in ene-yne cross metathesis.

  DOI：

  10.1021/jo202398q
• 作为产物：
  描述：

  3-((4E)(2R,3R)-3-hydroxy-2-methyl5-phenylpent-4-enoyl)(4S)-4-benzyl-1,3-oxazolidin-2-one 在 Hoveyda-Blechert second generation catalyst 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 12.0h， 以91%的产率得到(S)-4-benzyl-3-((2R,3R)-3-hydroxy-2-methylpent-4-enoyl)-oxazolidin-2-one
  参考文献：
  名称：

  Alkene Metathesis Approach to β-Unsubstituted Anti-Allylic Alcohols and Their Use in Ene–Yne Metathesis

  摘要：

  The synthesis of beta-unsubstituted, anti-allylic alcohols using a catalytic Evans aldol reaction conjoined with a relay-type ring-closing alkene metathesis is reported. The metathesis step serves to remove a beta-alkenyl group, which facilitated the aldol step. The beta-substituted enals serve as acrolein surrogates. The products were employed in ene-yne cross metathesis.

  DOI：

  10.1021/jo202398q

文献信息

• Alkene Metathesis Approach to β-Unsubstituted <i>Anti</i>-Allylic Alcohols and Their Use in Ene–Yne Metathesis
  作者：Joseph R. Clark、Jonathan M. French、Steven T. Diver

  DOI：10.1021/jo202398q

  日期：2012.2.3

  The synthesis of beta-unsubstituted, anti-allylic alcohols using a catalytic Evans aldol reaction conjoined with a relay-type ring-closing alkene metathesis is reported. The metathesis step serves to remove a beta-alkenyl group, which facilitated the aldol step. The beta-substituted enals serve as acrolein surrogates. The products were employed in ene-yne cross metathesis.