methyl (S)-2-({(S)-2-(4-bromophenyl)-2-[(2-methoxypropan-2-yl)oxy]ethyl}amino)-3-phenylpropanoate | 1225375-70-1

• 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: methyl (S)-2-({(S)-2-(4-bromophenyl)-2-[(2-methoxypropan-2-yl)oxy]ethyl}amino)-3-phenylpropanoate
• 英文别名: methyl (2S)-2-[[(2S)-2-(4-bromophenyl)-2-(2-methoxypropan-2-yloxy)ethyl]amino]-3-phenylpropanoate
• CAS: 1225375-70-1
• 化学式: C₂₂H₂₈BrNO₄
• 分子量: 450.373
• InChiKey: NDVYEJBFCOWLOK-VQTJNVASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (S)-2-({(S)-2-(4-bromophenyl)-2-[(2-methoxypropan-2-yl)oxy]ethyl}amino)-3-phenylpropanoate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以92%的产率得到(S)-2-({(S)-2-(4-bromophenyl)-2-[(2-methoxypropan-2-yl)oxy]ethyl}amino)-3-phenylpropan-1-ol
  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：

  (S)-2-(4-bromophenyl)-2-[(2-methoxypropan-2-yl)oxy]acetonitrile 、 L-苯丙氨酸甲酯盐酸盐 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， 以34%的产率得到methyl (S)-2-({(S)-2-(4-bromophenyl)-2-[(2-methoxypropan-2-yl)oxy]ethyl}amino)-3-phenylpropanoate
  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

文献信息

• Enantioselective Chemoenzymatic Synthesis of <i>cis-</i> and <i>trans</i>-2,5-Disubstituted Morpholines
  作者：Bas Ritzen、Steven Hoekman、Elena Durán Verdasco、Floris L. van Delft、Floris P. J. T. Rutjes

  DOI：10.1021/jo1003295

  日期：2010.5.21

  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.