(3S,4S)-ethyl 3-benzyl-2-oxo-6-phenyl-3,4-dihydro-2H-pyran-4-carboxylate | 1042450-56-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: (3S,4S)-ethyl 3-benzyl-2-oxo-6-phenyl-3,4-dihydro-2H-pyran-4-carboxylate
• 英文别名: ethyl (3S,4S)-3-benzyl-6-phenyl-2-oxo-3,4-dihydro-2H-pyran-4-carboxylate；ethyl (3S,4S)-3-benzyl-2-oxo-6-phenyl-3,4-dihydropyran-4-carboxylate
• CAS: 1042450-56-5
• 化学式: C₂₁H₂₀O₄
• 分子量: 336.387
• InChiKey: NDJRWSWNTODNMY-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 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：

  1-oxo-3-phenylpropan-2-yl 4-nitrobenzoate 、 反-3-苯甲酰丙烯酸乙酯 在 (5aR,10bS)-5a,10b-dihydro-2-(2,4,6-trimethylphenyl)-4H,6H-indeno[2,1-b]-1,2,4-triazolo[4,3-d]-1,4-oxazinium chloride 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以79%的产率得到(3S,4S)-ethyl 3-benzyl-2-oxo-6-phenyl-3,4-dihydro-2H-pyran-4-carboxylate
  参考文献：
  名称：

  Enantioselective NHC-catalysed redox [4+2]-hetero-Diels-Alder reactions using α-aroyloxyaldehydes and unsaturated ketoesters

  摘要：

  N-Heterocyclic carbene (NHC)-catalysed redox [4+2]-hetero-Diels-Alder reactions of alpha-aroyloxyaldehydes with either beta,gamma-unsaturated alpha-ketoesters or alpha,beta-unsaturated gamma-ketoesters generates substituted syn-dihydropyranones in good yield with excellent enantioselectivity (up to >99:1 er). The product diastereoselectivity is markedly dependent upon the nature of the unsaturated enone substituent. The presence of either electron-neutral or electron-rich aryl substituents gives excellent diastereoselectivity (up to >99:5 dr), while electron-deficient aryl substituents give reduced diastereoselectivity. In these cases, the syn-dihydropyranone products are more susceptible to base-promoted epimerisation at the C(4)-position under the reaction conditions, accounting for the lower diastereoselectivity obtained. (C) 2017 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2017.01.002

文献信息

• Chiral NHC-Catalyzed Oxodiene Diels−Alder Reactions with α-Chloroaldehyde Bisulfite Salts
  作者：Ming He、Brendan J. Beahm、Jeffrey W. Bode

  DOI：10.1021/ol801502h

  日期：2008.9.1

  hetero-Diels-Alder reactions with various oxodienes under biphasic reaction conditions with high levels of enantioselectivity. This new protocol makes possible enantioselective additions from commercially available chloroacetaldehyde sodium bisulfite and demonstrates that this unique class of catalysts readily tolerates aqueous conditions.

  在具有高水平对映选择性的双相反应条件下，α-氯醛亚硫酸氢盐加合物成功地用于手性 NHC 催化的杂-Diels-Alder 反应与各种氧代二烯。这种新的协议使得从市售的氯乙醛亚硫酸氢钠中进行对映选择性添加成为可能，并证明这种独特的催化剂类别很容易耐受水性条件。
• (1R,2R)-DPEN-derived triazolium salts for enantioselective oxodiene Diels–Alder reactions
  作者：Zi-Qiang Rong、Min-Qiang Jia、Shu-Li You

  DOI：10.1016/j.tet.2011.09.129

  日期：2011.12

  Enantioselective oxodiene Diels-Alder reactions catalyzed by (1R,2R)-DPEN-derived triazolium salts were realized successfully. With 0.5 mol % of (1R,2R)-DPEN-derived triazolium salt C and 150 mol % of Et3N, the reactions of various alpha-chloroaldehydes (alpha-bromoaldehyde) with substituted enones led to 3,4-dihydropyridinones and their derivatives in good yields, diastereoselectivities, and enantioselectivities (up to 97% ee). (C) 2011 Elsevier Ltd. All rights reserved.