ethyl (3R,4R)-4-butyl-2-hydroxy-6-methyl-3-propyl-3,4-dihydro-2H-pyran-5-carboxylate | 1032286-41-1

• 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: ethyl (3R,4R)-4-butyl-2-hydroxy-6-methyl-3-propyl-3,4-dihydro-2H-pyran-5-carboxylate
• CAS: 1032286-41-1
• 化学式: C₁₆H₂₈O₄
• 分子量: 284.396
• InChiKey: NDEZTGVNQCYGOT-HCYNLOQUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.39
• 重原子数：
  20.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 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：

  ethyl (3R,4R)-4-butyl-2-hydroxy-6-methyl-3-propyl-3,4-dihydro-2H-pyran-5-carboxylate 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到ethyl (3R,4R)-4-butyl-6-methyl-2-oxo-3-propyl-3,4-dihydro-2H-pyran-5-carboxylate
  参考文献：
  名称：

  ‘One-pot’ organocatalyzed enantioselective synthesis of highly functionalized 3,4,5,6-tetrasubstituted dihydropyrans by sequential Knoevenagel condensation/Michael addition and hemiacetalization

  摘要：

  An organocatalytic 'one-pot' synthesis of highly functionalized 3,4,5,6-tetrasubstituted dihydropyrans has been developed. Excellent enantio- and diastereo selectivity with good yields are some of the salient features of this methodology. This reaction takes advantage of proline based catalysts and follows stepwise sequential transformations including Knoevenagel condensation-Michael addition-hemiacetalization towards the synthesis of complex dihydropyranol framework. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.10.014
• 作为产物：
  描述：

  正戊醛 、 ethyl (Z)-2-acetyl-2-heptenoate 在 (2S)-2-[二苯基[(三甲基硅酯)氧基]甲基]-吡咯烷 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 25.0h， 以86%的产率得到ethyl (3R,4R)-4-butyl-2-hydroxy-6-methyl-3-propyl-3,4-dihydro-2H-pyran-5-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