furan-2-yl((2R,3S,4S)-4-hydroxy-2-phenyltetrahydrothiophen-3-yl)methanone | 1357912-60-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: furan-2-yl((2R,3S,4S)-4-hydroxy-2-phenyltetrahydrothiophen-3-yl)methanone
• CAS: 1357912-60-7
• 化学式: C₁₅H₁₄O₃S
• 分子量: 274.34
• InChiKey: YJEURJWQVJQWQW-ZLDLUXBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.93
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  50.44
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  1,4-二硫-2,5-二醇 、 1-(2-furyl)-3-phenylpropen-1-one 在 C₃₂H₂₈F₆N₄O₃ 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以82%的产率得到furan-2-yl((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

• Enantioselective one-pot synthesis of β-sulfonyl ketones and trisubstituted tetrahydrothiophenes via β-elimination/cycloaddition sequence
  作者：Lu Xue、Yidong Liu、Wenling Qin、Hailong Yan

  DOI：10.1016/j.cclet.2018.01.047

  日期：2018.8

  Abstract A mild and efficient enantioselective one-pot synthesis of β-sulfonyl ketones and trisubstituted tetrahydrothiophenes via introducing 1,4-dithiane-2,5-diol to the simple kinetic resolution of β-sulfonyl ketones has been described herein. The one-pot reaction sequence including kinetic resolution and cascade sulfa-Michael/Aldol reaction proceeded successively to afford corresponding sulfonyl

  摘要本文介绍了通过引入1,4-二噻吩-2,5-二醇以简单动力学拆分β-磺酰基酮的温和有效的对映选择性一锅合成β-磺酰基酮和三取代的四氢噻吩的方法。依次进行包括动力学拆分和级联磺胺-迈克尔/阿尔多反应在内的一锅反应序列，得到具有高对映选择性（85％–98％ee和84％–95％ee）的相应磺酰基酮和四氢噻吩。