ethyl (R)-dimethyl-6-oxo-5,6-dihydro-4H-pyran-3-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: ethyl (R)-dimethyl-6-oxo-5,6-dihydro-4H-pyran-3-carboxylate
• 英文别名: ethyl (R)-4,6-dimethyl-2-oxo-3,4-dihydro-2H-pyran-5-carboxylate；ethyl (4R)-4,6-dimethyl-2-oxo-3,4-dihydropyran-5-carboxylate
• 化学式: C₁₀H₁₄O₄
• 分子量: 198.219
• InChiKey: ZJIWXABJOMRNLJ-ZCFIWIBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  ethyl (3R)-2-acetyl-3-methyl-5-oxo-5-(2-thioxothiazolidin-3-yl)pentanoate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 生成 ethyl (R)-dimethyl-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

• Chiral N-heterocyclic carbene catalyzed annulation of α,β-unsaturated aldehydes with 1,3-dicarbonyls
  作者：Zhi-Qiang Zhu、Xing-Liang Zheng、Ning-Fei Jiang、Xiaolong Wan、Ji-Chang Xiao

  DOI：10.1039/c1cc12778k

  日期：——

  Chiral N-heterocyclic carbene catalyzed annulations of ynals and enals with 1,3-dicarbonyls have been described. The two reactions provided direct and efficient methods for enantioselective synthesis of functionalized dihydropyranones. Comparatively, the reactions starting from ynals were atom-economical; furthermore the reactions of enals demonstrated broader substrate compatibility.

  已经描述了手性N-杂环卡宾催化的具有1，3-二羰基的烯醛和烯醛的环。这两个反应为功能化二氢吡喃酮的对映选择性合成提供了直接和有效的方法。相比之下，从自醛开始的反应是原子经济的。此外，烯醛的反应证明了更广泛的底物相容性。