3-((3,5-difluorophenyl)(phenylamino)methyl)tetrahydrothiopyran-4-one

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-((3,5-difluorophenyl)(phenylamino)methyl)tetrahydrothiopyran-4-one
• 英文别名: (3R)-3-[(S)-anilino-(3,5-difluorophenyl)methyl]thian-4-one
• 化学式: C₁₈H₁₇F₂NOS
• 分子量: 333.402
• InChiKey: GZRHAZVMOMIKFP-FUHWJXTLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  四氢噻喃-4-酮 、 3,5-二氟苯甲醛 、 苯胺 在 rac-BINOL derivative 作用下， 以 甲苯 为溶剂， 反应 24.0h， 生成 3-((3,5-difluorophenyl)(phenylamino)methyl)tetrahydrothiopyran-4-one
  参考文献：
  名称：

  Chiral Brønsted Acid-Catalyzed Direct Asymmetric Mannich Reaction

  摘要：

  A chiral Bronsted acid-catalyzed direct asymmetric Mannich reaction has been described. Various phosphoric acids, prepared from BINOL and H-8-BINOL derivatives, have been evaluated for catalyzing the direct Mannich reaction. In the presence of a truly catalytic amount of the phosphoric acid, anti-selective Mannich reactions of cyclic ketones with a wide scope of aldimines were obtained in high yields with excellent enantioselectivities (up to 98% ee) and high diastereomeric ratios (up to 98/2 dr). A one-pot Mannich reaction using aromatic ketones as donors proceeded smoothly to give beta-amino carbonyls with fairly good enantioselectivities.

  DOI：

  10.1021/ja068236b

文献信息

• Chiral Brønsted Acid-Catalyzed Direct Asymmetric Mannich Reaction
  作者：Qi-Xiang Guo、Hua Liu、Chang Guo、Shi-Wei Luo、Yi Gu、Liu-Zhu Gong

  DOI：10.1021/ja068236b

  日期：2007.4.1

  A chiral Bronsted acid-catalyzed direct asymmetric Mannich reaction has been described. Various phosphoric acids, prepared from BINOL and H-8-BINOL derivatives, have been evaluated for catalyzing the direct Mannich reaction. In the presence of a truly catalytic amount of the phosphoric acid, anti-selective Mannich reactions of cyclic ketones with a wide scope of aldimines were obtained in high yields with excellent enantioselectivities (up to 98% ee) and high diastereomeric ratios (up to 98/2 dr). A one-pot Mannich reaction using aromatic ketones as donors proceeded smoothly to give beta-amino carbonyls with fairly good enantioselectivities.