(3-bromophenyl)((2R,3S,4S)-4-hydroxy-2-phenyltetrahydrothiophen-3-yl)methanone | 1357912-55-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3-bromophenyl)((2R,3S,4S)-4-hydroxy-2-phenyltetrahydrothiophen-3-yl)methanone
• 英文别名: (3-bromophenyl)-[(2R,3S,4S)-4-hydroxy-2-phenylthiolan-3-yl]methanone
• CAS: 1357912-55-0
• 化学式: C₁₇H₁₅BrO₂S
• 分子量: 363.275
• InChiKey: YAFLJFQMNMZQLJ-VYDXJSESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,4-二硫-2,5-二醇 、 1-(3-bromophenyl)-3-phenylprop-2-en-1-one 在 C₃₂H₂₈F₆N₄O₃ 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以88%的产率得到(3-bromophenyl)((2R,3S,4S)-4-hydroxy-2-phenyltetrahydrothiophen-3-yl)methanone
  参考文献：
  名称：

  Hydrogen-Bond-Mediated Cascade Reaction Involving Chalcones: Facile Synthesis of Enantioenriched Trisubstituted Tetrahydrothiophenes

  摘要：

  A bifunctional squaramide catalyzed sulfa-Michael/aldol cascade reaction between 1,4-dithiane-2,5-diol and chalcones with a low catalyst loading has been developed. Trisubstituted tetrahydrothiophenes with three contiguous stereogenic centers are obtained in a highly stereocontrolled manner. Additionally, a remarkable temperature effect on reaction efficiency was observed and a synthetically potential gram-synthesis was also conducted.

  DOI：

  10.1021/ol2034959

文献信息

• Hydrogen-Bond-Mediated Cascade Reaction Involving Chalcones: Facile Synthesis of Enantioenriched Trisubstituted Tetrahydrothiophenes
  作者：Jun-Bing Ling、Yu Su、Hai-Liang Zhu、Guan-Yu Wang、Peng-Fei Xu

  DOI：10.1021/ol2034959

  日期：2012.2.17

  A bifunctional squaramide catalyzed sulfa-Michael/aldol cascade reaction between 1,4-dithiane-2,5-diol and chalcones with a low catalyst loading has been developed. Trisubstituted tetrahydrothiophenes with three contiguous stereogenic centers are obtained in a highly stereocontrolled manner. Additionally, a remarkable temperature effect on reaction efficiency was observed and a synthetically potential gram-synthesis was also conducted.