(S)-2-(2-furyl)-2-[(2-methoxypropan-2-yl)oxy]acetonitrile | 1225375-61-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-2-(2-furyl)-2-[(2-methoxypropan-2-yl)oxy]acetonitrile
• CAS: 1225375-61-0
• 化学式: C₁₀H₁₃NO₃
• 分子量: 195.218
• InChiKey: QIEXCYVCVVFQSB-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.24
• 重原子数：
  14.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.39
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (S)-2-(2-furyl)-2-[(2-methoxypropan-2-yl)oxy]acetonitrile 在 二异丁基氢化铝 、 甲醇 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  Enantioselective Chemoenzymatic Synthesis of cis- and trans-2,5-Disubstituted Morpholines

  摘要：

  A versatile synthesis of enantiomerically pure cis- and trans-2,5-disubstituted morpholines is described. Hydroxynitrile lyase-mediated cyanide addition onto aldehydes provided cyanohydrins in virtually quantitative yield and excellent enantioselectivity. Subsequent formation of diastereomerically pure amino esters via a three-step, one-pot reduction-transimination-reduction sequence followed by reduction and simultaneous protection provided cyclization precursors. Finally, cyclization and SmI2-mediated reductive detosylation completed the synthesis of cis- and trans-2,5-disubstituted morpholines in good yields and excellent diastereoselectivities.

  DOI：

  10.1021/jo1003295
• 作为产物：
  描述：

  (2S)-2-呋喃基(羟基)乙腈 、 2-甲氧基丙烯 在 三氯氧磷 、 三乙胺 作用下， 反应 0.42h， 以2.01 g的产率得到(S)-2-(2-furyl)-2-[(2-methoxypropan-2-yl)oxy]acetonitrile
  参考文献：
  名称：

  Enantioselective Chemoenzymatic Synthesis of cis- and trans-2,5-Disubstituted Morpholines

  摘要：

  A versatile synthesis of enantiomerically pure cis- and trans-2,5-disubstituted morpholines is described. Hydroxynitrile lyase-mediated cyanide addition onto aldehydes provided cyanohydrins in virtually quantitative yield and excellent enantioselectivity. Subsequent formation of diastereomerically pure amino esters via a three-step, one-pot reduction-transimination-reduction sequence followed by reduction and simultaneous protection provided cyclization precursors. Finally, cyclization and SmI2-mediated reductive detosylation completed the synthesis of cis- and trans-2,5-disubstituted morpholines in good yields and excellent diastereoselectivities.

  DOI：

  10.1021/jo1003295