2-Allyloxy-pentanal | 250670-78-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Allyloxy-pentanal
• 英文别名: 2-Prop-2-enoxypentanal
• CAS: 250670-78-1
• 化学式: C₈H₁₄O₂
• 分子量: 142.198
• InChiKey: OYWHBTZNVNSHQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  10
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  氢氰酸 、 2-Allyloxy-pentanal 在 (R)-PaHNL 作用下， 以 异丙醚 为溶剂， 反应 48.0h， 以98%的产率得到(S)-3-Allyloxy-2-hydroxy-hexanenitrile
  参考文献：
  名称：

  Hydroxynitrile lyase catalyzed enantioselective HCN addition to O-protected α-hydroxyaldehydes

  摘要：

  Various O-protected glycol- and racemic lactaldehydes 3 and 6 as well as O-allyl protected racemic alpha-hydroxyaldehydes 7 (R-1=Et Pr, Bu) have been prepared to investigate and perform a stereoselective Kiliani-Fischer synthesis by hydroxynitrile lyase (HNL) catalyzed addition of HCN. From all protecting groups investigated the allyl moiety was most suitable. (R)-PaHNL from bitter almonds (Prunus amygdalus), yielding the (2S)-cyanohydrins 8-10, was found to be a more stereoselective catalyst than (S)-MeHNL from maniok (Manihot esculenta). While (R)-PaHNL led to enantiomeric excesses greater than or equal to 93%, with (S)-MeHNL the (2R)-cyanohydrins 8-10 were obtained with enantiomeric excesses less than or equal to 78%. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00275-x
• 作为产物：
  描述：

  2-羟基戊酸甲酯 在 sodium hydride 、 二异丁基氢化铝 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 12.5h， 生成 2-Allyloxy-pentanal
  参考文献：
  名称：

  Hydroxynitrile lyase catalyzed enantioselective HCN addition to O-protected α-hydroxyaldehydes

  摘要：

  Various O-protected glycol- and racemic lactaldehydes 3 and 6 as well as O-allyl protected racemic alpha-hydroxyaldehydes 7 (R-1=Et Pr, Bu) have been prepared to investigate and perform a stereoselective Kiliani-Fischer synthesis by hydroxynitrile lyase (HNL) catalyzed addition of HCN. From all protecting groups investigated the allyl moiety was most suitable. (R)-PaHNL from bitter almonds (Prunus amygdalus), yielding the (2S)-cyanohydrins 8-10, was found to be a more stereoselective catalyst than (S)-MeHNL from maniok (Manihot esculenta). While (R)-PaHNL led to enantiomeric excesses greater than or equal to 93%, with (S)-MeHNL the (2R)-cyanohydrins 8-10 were obtained with enantiomeric excesses less than or equal to 78%. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00275-x