(2R^*,2'S^*)-2-<1-(phenylthio)propyl>-2,3-dihydro-4H-pyran-4-one | 140928-69-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (2R^*,2'S^*)-2-<1-(phenylthio)propyl>-2,3-dihydro-4H-pyran-4-one
• 英文别名: (2R)-2-[(1S)-1-phenylsulfanylpropyl]-2,3-dihydropyran-4-one
• CAS: 140928-69-4
• 化学式: C₁₄H₁₆O₂S
• 分子量: 248.346
• InChiKey: AQFKCHFTASEUTE-KGLIPLIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R^*,2'S^*)-2-<1-(phenylthio)propyl>-2,3-dihydro-4H-pyran-4-one 在 L-Selectride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 苯 为溶剂， 生成 (2R^*,2'S^*)-7-<1-(phenylthio)propyl>-1,4,8-trioxaspiro<4.5>decane
  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
• 作为产物：
  描述：

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