methyl (2S,3R,4S)-2-hydroxy-4-phenyl-3-propyl-3,4-dihydro-2H-pyran-6-carboxylate | 1032287-29-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl (2S,3R,4S)-2-hydroxy-4-phenyl-3-propyl-3,4-dihydro-2H-pyran-6-carboxylate
• CAS: 1032287-29-8
• 化学式: C₁₆H₂₀O₄
• 分子量: 276.332
• InChiKey: MBPKMKFNGWDLNP-NFAWXSAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.59
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl (2S,3R,4S)-2-hydroxy-4-phenyl-3-propyl-3,4-dihydro-2H-pyran-6-carboxylate 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 以76%的产率得到methyl (3R,4S)-2-oxo-4-phenyl-3-propyl-3,4-dihydro-2H-pyran-6-carboxylate
  参考文献：
  名称：

  Enantioselective Assembly of Substituted Dihydropyrones via Organocatalytic Reaction in Water Media

  摘要：

  The diarylprolinol ether/HOAc-catalyzed cascade Michael addition and cyclization of aldehydes and alpha-keto-alpha,beta-unsaturated esters proceeds smoothly in water to afford cyclic hemiacetals, which are oxidized to furnish highly functionalized 3,4,5,6-tetrasubstituted dihydropyrones with excellent enantioselectivities.

  DOI：

  10.1021/ol800835m
• 作为产物：
  描述：

  正戊醛 、 methyl 4-phenyl-2-oxo-3-butenoate 在 (2S)-2-[二苯基[(三甲基硅酯)氧基]甲基]-吡咯烷 、 苯甲酸 作用下， 以 水 为溶剂， 以72%的产率得到methyl (2S,3R,4S)-2-hydroxy-4-phenyl-3-propyl-3,4-dihydro-2H-pyran-6-carboxylate
  参考文献：
  名称：

  Enantioselective Assembly of Substituted Dihydropyrones via Organocatalytic Reaction in Water Media

  摘要：

  The diarylprolinol ether/HOAc-catalyzed cascade Michael addition and cyclization of aldehydes and alpha-keto-alpha,beta-unsaturated esters proceeds smoothly in water to afford cyclic hemiacetals, which are oxidized to furnish highly functionalized 3,4,5,6-tetrasubstituted dihydropyrones with excellent enantioselectivities.

  DOI：

  10.1021/ol800835m

文献信息

• Highly Enantioselective Inverse-Electron-Demand Hetero-Diels-Alder Reactions Catalyzed by Modularly Designed Organocatalysts
  作者：Debarshi Sinha、Sandun Perera、John Cong-Gui Zhao

  DOI：10.1002/chem.201300168

  日期：2013.5.27

  rocks! Proline and (2S,3aS,7aS)‐octahydro‐1H‐indole‐2‐carboxylic acid are both poor catalysts for the inverse‐electron‐demand hetero‐Diels–Alder reactions between aldehydes and electron‐deficient enones. However, forming modularly designed organocatalysts (MDOs) through their self‐assembly with cinchona alkaloid‐derived thioureas can dramatically improve the efficiency of these catalysts (see scheme;

  MDO震撼！脯氨酸和（2 S，3a S，7a S）-八氢-1 H-吲哚-2-羧酸都是醛和缺电子的烯酮之间反电子需求的杂Diels-Alder反应的不良催化剂。但是，通过与金鸡纳生物碱衍生的硫脲的自组装形成模块化设计的有机催化剂（MDO）可以显着提高这些催化剂的效率（请参见方案； PCC =氯铬酸吡啶鎓）。