diethyl 2-allyl-2-((4R,5R,E)-6-((S)-4-benzyl-2-oxooxazolidin-3-yl)-4-hydroxy-5-methyl-6-oxohex-2-enyl)malonate | 1354716-14-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: diethyl 2-allyl-2-((4R,5R,E)-6-((S)-4-benzyl-2-oxooxazolidin-3-yl)-4-hydroxy-5-methyl-6-oxohex-2-enyl)malonate
• 英文别名: diethyl 2-[(E,4R,5R)-6-[(4S)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-4-hydroxy-5-methyl-6-oxohex-2-enyl]-2-prop-2-enylpropanedioate
• CAS: 1354716-14-5
• 化学式: C₂₇H₃₅NO₈
• 分子量: 501.577
• InChiKey: YLFBZKPIYDARMC-IDVRTYTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  36
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  119
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  diethyl 2-allyl-2-((4R,5R,E)-6-((S)-4-benzyl-2-oxooxazolidin-3-yl)-4-hydroxy-5-methyl-6-oxohex-2-enyl)malonate 在 Hoveyda-Blechert second generation catalyst 作用下， 以 乙烯 、 甲苯 为溶剂， 60.0 ℃ 、101.33 kPa 条件下， 反应 12.0h， 以83%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
• 作为产物：
  描述：

  在 三氟乙酸 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以1.38 g的产率得到diethyl 2-allyl-2-((4R,5R,E)-6-((S)-4-benzyl-2-oxooxazolidin-3-yl)-4-hydroxy-5-methyl-6-oxohex-2-enyl)malonate
  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.