(S)-2-({(R)-2-[(2-methoxypropan-2-yl)oxy]-2-phenylethyl}amino)propan-1-ol | 1225375-73-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-2-({(R)-2-[(2-methoxypropan-2-yl)oxy]-2-phenylethyl}amino)propan-1-ol
• 英文别名: (2S)-2-[[(2R)-2-(2-methoxypropan-2-yloxy)-2-phenylethyl]amino]propan-1-ol
• CAS: 1225375-73-4
• 化学式: C₁₅H₂₅NO₃
• 分子量: 267.368
• InChiKey: SQKVVMNJYXCXSA-JSGCOSHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  50.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2-({(R)-2-[(2-methoxypropan-2-yl)oxy]-2-phenylethyl}amino)propan-1-ol 、 对甲苯磺酰氯 在 吡啶 、 三乙胺 、 乙二胺 作用下， 反应 2.5h， 以80%的产率得到(S)-2-(N-{(R)-2-[(2-methoxypropan-2-yl)oxy]-2-phenylethyl}-4-methylbenzenesulfonamido)propyl 4-methylbenzenesulfonate
  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：

  methyl (S)-2({(R)-2-[(2-methoxypropan-2-yl)oxy]-2-phenylethyl}amino)propanoate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以92%的产率得到(S)-2-({(R)-2-[(2-methoxypropan-2-yl)oxy]-2-phenylethyl}amino)propan-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

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.