tert-butyl (4R,5R)-5-benzyl-2-ethyl-4-methyl-6-oxo-5,6-dihydro-4H-pyran-3-carboxylate | 864516-18-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: tert-butyl (4R,5R)-5-benzyl-2-ethyl-4-methyl-6-oxo-5,6-dihydro-4H-pyran-3-carboxylate
• 英文别名: tert-butyl (3R,4R)-3-benzyl-6-ethyl-4-methyl-2-oxo-3,4-dihydro-2H-pyran-5-carboxylate；tert-butyl (3R,4R)-3-benzyl-6-ethyl-4-methyl-2-oxo-3,4-dihydropyran-5-carboxylate
• CAS: 864516-18-7
• 化学式: C₂₀H₂₆O₄
• 分子量: 330.424
• InChiKey: DMGQGBZEQDPTAN-UKRRQHHQSA-N

物化性质

• 沸点：
  442.5±45.0 °C(Predicted)
• 密度：
  1.078±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (4R,5R)-5-benzyl-2-ethyl-4-methyl-6-oxo-5,6-dihydro-4H-pyran-3-carboxylate 在 lithium hydroxide 、 二甲基硫 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 反应 2.5h， 生成 (2R,3S)-2-benzyl-3-methyl-5-oxoheptanoic acid
  参考文献：
  名称：

  Ni(II) Tol-BINAP-Catalyzed Enantioselective Michael Reactions of β-Ketoesters and Unsaturated N-Acylthiazolidinethiones

  摘要：

  The enantioselective addition of beta-ketoesters to unsaturated N-acylthiazolidinethiones catalyzed by Ni(II) Tol-BINAP Lewis acid complexes is reported. Notable features of this reaction are its operation simplicity, the obviated need for the addition of an external base, and the ease with which the adducts are converted into a range of potentially useful derivatives. In particular, the dihydropyrone adducts are versatile scaffolds for further stereoselective elaboration.

  DOI：

  10.1021/ja053820q
• 作为产物：
  描述：

  tert-butyl (3R)-3-methyl-5-oxo-2-propionyl-5-(2-thioxothiazolidin-3-yl)pentanoate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 tert-butyl (4R,5R)-5-benzyl-2-ethyl-4-methyl-6-oxo-5,6-dihydro-4H-pyran-3-carboxylate
  参考文献：
  名称：

  Ni(II) Tol-BINAP-Catalyzed Enantioselective Michael Reactions of β-Ketoesters and Unsaturated N-Acylthiazolidinethiones

  摘要：

  The enantioselective addition of beta-ketoesters to unsaturated N-acylthiazolidinethiones catalyzed by Ni(II) Tol-BINAP Lewis acid complexes is reported. Notable features of this reaction are its operation simplicity, the obviated need for the addition of an external base, and the ease with which the adducts are converted into a range of potentially useful derivatives. In particular, the dihydropyrone adducts are versatile scaffolds for further stereoselective elaboration.

  DOI：

  10.1021/ja053820q

文献信息

• Enantioselective Assembly of Substituted Dihydropyrones via Organocatalytic Reaction in Water Media
  作者：Jing Wang、Fang Yu、Xiaojing Zhang、Dawei Ma

  DOI：10.1021/ol800835m

  日期：2008.6.1

  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.
• Ni(II) Tol-BINAP-Catalyzed Enantioselective Michael Reactions of β-Ketoesters and Unsaturated <i>N</i>-Acylthiazolidinethiones
  作者：David A. Evans、Regan J. Thomson、Francisco Franco

  DOI：10.1021/ja053820q

  日期：2005.8.1

  The enantioselective addition of beta-ketoesters to unsaturated N-acylthiazolidinethiones catalyzed by Ni(II) Tol-BINAP Lewis acid complexes is reported. Notable features of this reaction are its operation simplicity, the obviated need for the addition of an external base, and the ease with which the adducts are converted into a range of potentially useful derivatives. In particular, the dihydropyrone adducts are versatile scaffolds for further stereoselective elaboration.