methyl (5R,6S)-1,7-dioxo-5-phenyl-2-oxaspiro[5.5]undec-3-ene-3-carboxylate | 1225464-91-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: methyl (5R,6S)-1,7-dioxo-5-phenyl-2-oxaspiro[5.5]undec-3-ene-3-carboxylate
• 英文别名: (+)-methyl 1,7-dioxo-5-phenyl-2-oxaspiro[5.5]undec-3-ene-3-carboxylate；methyl (5R,6S)-1,11-dioxo-5-phenyl-2-oxaspiro[5.5]undec-3-ene-3-carboxylate
• CAS: 1225464-91-4
• 化学式: C₁₈H₁₈O₅
• 分子量: 314.338
• InChiKey: YANSQOYBLYKNSY-ACJLOTCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 生成 methyl (5R,6S)-1,7-dioxo-5-phenyl-2-oxaspiro[5.5]undec-3-ene-3-carboxylate
  参考文献：
  名称：

  Bifuctional Amino-Squaramides Catalyzed Asymmetric Spiroannulation Cascades with Aliphatic β,γ-Unsaturated α-Keto Esters: Controlling an Aldehyde Enolate

  摘要：

  A quinidine-derived squaramide Ib catalyzed cyclization reaction of beta-oxo aldehydes 1 and aliphatic or aromatic beta,gamma-unsaturated alpha-keto ester 2 is described. Using cyclic aldehyde substrates, this procedure provided a promising approach to a variety of spiro-3,4-dihydropyrans bearing three continuous quaternary and tertiary stereocenters in moderate to good yield with high stereoselectivities. Substituents on the nitrogen atoms of the squaramide moiety of the catalyst proved crucial to the reaction outcome. The stereochemistry of the three newly formed chiral centers (trans-selective) of the major product indicates a Micheal addition/hemiacetalization domino sequence for the present annulations.

  DOI：

  10.1021/jo202633c

文献信息

• Asymmetric Synthesis of Spiro-3,4-dihydropyrans via a Domino Organocatalytic Sequence
  作者：Weijun Yao、Lianjie Pan、Yihua Wu、Cheng Ma

  DOI：10.1021/ol1007873

  日期：2010.5.21

  A cinchona alkaloid-catalyzed domino Michael/hemiacetalization reaction of cyclic beta-oxo aldehydes and aromatic beta,gamma-unsaturated a-keto esters, resulting in the formation of spiro-dihydropyran architectures in good yield with high stereoselectivity (up to 97% ee), is presented.
• Bifuctional Amino-Squaramides Catalyzed Asymmetric Spiroannulation Cascades with Aliphatic β,γ-Unsaturated α-Keto Esters: Controlling an Aldehyde Enolate
  作者：Xiaoqin Wang、Weijun Yao、Zhihui Yao、Cheng Ma

  DOI：10.1021/jo202633c

  日期：2012.3.16

  A quinidine-derived squaramide Ib catalyzed cyclization reaction of beta-oxo aldehydes 1 and aliphatic or aromatic beta,gamma-unsaturated alpha-keto ester 2 is described. Using cyclic aldehyde substrates, this procedure provided a promising approach to a variety of spiro-3,4-dihydropyrans bearing three continuous quaternary and tertiary stereocenters in moderate to good yield with high stereoselectivities. Substituents on the nitrogen atoms of the squaramide moiety of the catalyst proved crucial to the reaction outcome. The stereochemistry of the three newly formed chiral centers (trans-selective) of the major product indicates a Micheal addition/hemiacetalization domino sequence for the present annulations.