ethyl 2-methallyoxyacetate | 250671-13-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 2-methallyoxyacetate
• 英文别名: Ethyl 2-(2-methylprop-2-enoxy)propanoate
• CAS: 250671-13-7
• 化学式: C₉H₁₆O₃
• 分子量: 172.224
• InChiKey: VUQRXZKWNHHKEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 2-methallyoxyacetate 在 (R)-PaHNL 、 二异丁基氢化铝 作用下， 以 乙醚 、 正己烷 、 异丙醚 为溶剂， 反应 24.0h， 生成 (S)-2-Hydroxy-3-(2-methyl-allyloxy)-butyronitrile
  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：

  乙醇酸乙酯 、 3-氯-2-甲基丙烯 在 sodium hydride 作用下， 生成 ethyl 2-methallyoxyacetate
  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

文献信息

• Hydroxynitrile lyase catalyzed enantioselective HCN addition to O-protected α-hydroxyaldehydes
  作者：Jürgen Roos、Franz Effenberger

  DOI：10.1016/s0957-4166(99)00275-x

  日期：1999.7

  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.