2-(Benzenesulfonyl)-1-(4-methoxyphenyl)butan-1-one | 31663-23-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(Benzenesulfonyl)-1-(4-methoxyphenyl)butan-1-one
• CAS: 31663-23-7
• 化学式: C₁₇H₁₈O₄S
• 分子量: 318.394
• InChiKey: KIKHSHXLRZDNMR-UHFFFAOYSA-N

物化性质

• 熔点：
  104-105 °C
• 沸点：
  528.4±46.0 °C(Predicted)
• 密度：
  1.203±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  68.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(Benzenesulfonyl)-1-(4-methoxyphenyl)butan-1-one 在 吡啶硼烷 、 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成 、
  参考文献：
  名称：

  Efficient Diastereoselective Syntheses of erythro- or threo-α-Alkyl-β-hydroxy Sulfones by Reductions of α-Alkyl-β-keto Sulfones with TiCl₄/BH₃ or LiEt₃BH/CeCl₃, Respectively

  摘要：

  A stereoselective synthesis of erythro- and threo-alpha-alkyl-beta-hydroxy sulfones by reduction of the corresponding alpha-alkyl-beta-keto sulfones has I,een developed. The pivotal role in this methodology is played by the chelating or nonchelating properties of the Lewis acid employed. The strong chelating TiCl4 led to the erythro isomer in high diastereomeric excess in noncoordinating solvents (CH2Cl2) at -78 degrees C using BH3/py as reducing agent, while the nonchelating CeCl3 gave a high excess of the three isomer in coordinating solvents (THF) at the same temperature using lithium triethylborohydride (LiEt3BH) as reducing agent. Moreover, this methodology has been successfully utilized for the synthesis of alpha-allyl-beta-hydroxy sulfones, which are useful synthetic intermediates to obtain 2,5-disubstituted tetrahydrofurans by electrophilic cyclization.

  DOI：

  10.1021/jo972284k
• 作为产物：
  描述：

  (丙基磺酰基)-苯 、 茴香酸乙酯 在 2,2,6,6-tetramethylpiperidinyl-lithium 作用下， 生成 2-(Benzenesulfonyl)-1-(4-methoxyphenyl)butan-1-one
  参考文献：
  名称：

  Efficient Diastereoselective Syntheses of erythro- or threo-α-Alkyl-β-hydroxy Sulfones by Reductions of α-Alkyl-β-keto Sulfones with TiCl₄/BH₃ or LiEt₃BH/CeCl₃, Respectively

  摘要：

  A stereoselective synthesis of erythro- and threo-alpha-alkyl-beta-hydroxy sulfones by reduction of the corresponding alpha-alkyl-beta-keto sulfones has I,een developed. The pivotal role in this methodology is played by the chelating or nonchelating properties of the Lewis acid employed. The strong chelating TiCl4 led to the erythro isomer in high diastereomeric excess in noncoordinating solvents (CH2Cl2) at -78 degrees C using BH3/py as reducing agent, while the nonchelating CeCl3 gave a high excess of the three isomer in coordinating solvents (THF) at the same temperature using lithium triethylborohydride (LiEt3BH) as reducing agent. Moreover, this methodology has been successfully utilized for the synthesis of alpha-allyl-beta-hydroxy sulfones, which are useful synthetic intermediates to obtain 2,5-disubstituted tetrahydrofurans by electrophilic cyclization.

  DOI：

  10.1021/jo972284k

文献信息

• Samuelsson,B.; Lamm,B., Acta Chemica Scandinavica (1947), 1971, vol. 25, p. 1555 - 1558
  作者：Samuelsson,B.、Lamm,B.

  DOI：——

  日期：——
• Efficient Diastereoselective Syntheses of <i>erythro</i>- or <i>threo</i>-α-Alkyl-β-hydroxy Sulfones by Reductions of α-Alkyl-β-keto Sulfones with TiCl₄/BH₃ or LiEt₃BH/CeCl₃, Respectively
  作者：Enrico Marcantoni、Simone Cingolani、Giuseppe Bartoli,*、Marcella Bosco、Letizia Sambri

  DOI：10.1021/jo972284k

  日期：1998.5.1

  A stereoselective synthesis of erythro- and threo-alpha-alkyl-beta-hydroxy sulfones by reduction of the corresponding alpha-alkyl-beta-keto sulfones has I,een developed. The pivotal role in this methodology is played by the chelating or nonchelating properties of the Lewis acid employed. The strong chelating TiCl4 led to the erythro isomer in high diastereomeric excess in noncoordinating solvents (CH2Cl2) at -78 degrees C using BH3/py as reducing agent, while the nonchelating CeCl3 gave a high excess of the three isomer in coordinating solvents (THF) at the same temperature using lithium triethylborohydride (LiEt3BH) as reducing agent. Moreover, this methodology has been successfully utilized for the synthesis of alpha-allyl-beta-hydroxy sulfones, which are useful synthetic intermediates to obtain 2,5-disubstituted tetrahydrofurans by electrophilic cyclization.