(2R^*,2'S^*)-2-<2-methyl-1-(methylthio)propyl>-2,3-dihydro-4H-pyran-4-one | 140928-75-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (2R^*,2'S^*)-2-<2-methyl-1-(methylthio)propyl>-2,3-dihydro-4H-pyran-4-one
• 英文别名: (2R)-2-[(1S)-2-methyl-1-methylsulfanylpropyl]-2,3-dihydropyran-4-one
• CAS: 140928-75-2
• 化学式: C₁₀H₁₆O₂S
• 分子量: 200.302
• InChiKey: AHBIAXBDCZYWBF-ZJUUUORDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (E)-3-(tert-butyldimethylsilyloxy)-1-methoxy-1,3-butadiene 、 3-methyl-2-(methylthio)butanal 在 三氟化硼乙醚 水 、 三氟乙酸 作用下， 生成 (2S*,2'S*)-2-<2-methyl-1-(methylthio)propyl>-2,3-dihydro-4H-pyran-4-one 、 (2R^*,2'S^*)-2-<2-methyl-1-(methylthio)propyl>-2,3-dihydro-4H-pyran-4-one
  参考文献：
  名称：

  Diastereoselective cyclocondensation of electron-rich dienes with chiral thio-substituted aldehydes

  摘要：

  The Lewis acid-promoted cyclocondensation between two electron -rich dienes with a series of racemic alpha- and beta-thio-substituted aldehydes has been studied. Boron trifluoride etherate proved to be the catalyst of choice, affording satisfactory chemical yields and generally good diastereoselectivities. Other Lewis acidic catalysts gave lower yields and in some cases reversed the sense of the diastereoselection. A rationalization of the stereochemical results is presented.

  DOI：

  10.1021/jo00039a019

文献信息

• Diastereoselective cyclocondensation of electron-rich dienes with chiral thio-substituted aldehydes
  作者：Rita Annunziata、Mauro Cinquini、Franco Cozzi、Pier Giorgio Cozzi、Laura Raimondi

  DOI：10.1021/jo00039a019

  日期：1992.6

  The Lewis acid-promoted cyclocondensation between two electron -rich dienes with a series of racemic alpha- and beta-thio-substituted aldehydes has been studied. Boron trifluoride etherate proved to be the catalyst of choice, affording satisfactory chemical yields and generally good diastereoselectivities. Other Lewis acidic catalysts gave lower yields and in some cases reversed the sense of the diastereoselection. A rationalization of the stereochemical results is presented.