3-((4-chlorophenyl)(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-((4-chlorophenyl)(phenylamino)methyl)tetrahydrothiopyran-4-one
• 英文别名: (3R)-3-[(S)-anilino-(4-chlorophenyl)methyl]thian-4-one
• 化学式: C₁₈H₁₈ClNOS
• 分子量: 331.866
• InChiKey: KVHKEQURHOOBNS-FUHWJXTLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 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：
  3

反应信息

• 作为产物：
  描述：

  四氢噻喃-4-酮 、 4-氯苯甲醛 、 苯胺 在 rac-BINOL derivative 作用下， 以 甲苯 为溶剂， 反应 24.0h， 生成 3-((4-chlorophenyl)(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

• Squaric Acid Catalyzed Highly Efficient Three-Component Mannich-Type Reaction
  作者：Najmadin Azizi、Anahita Davoudpour

  DOI：10.1007/s10562-011-0669-0

  日期：2011.10

  Squaric acid catalyzed three-component Mannich reaction of aromatic aldehydes, aromatic amines and cyclic ketones in water and solvent-free conditions at room temperature. This protocol has several advantages such as good yields, mild conditions, novel organocatalyst, and good anti selectivities.Graphical AbstractSquaric acid catalyzed three-component Mannich reaction of aromatic aldehydes, aromatic

  方酸在室温和无溶剂条件下在水中催化芳香醛、芳香胺和环酮的三组分曼尼希反应。该方案具有收率好、条件温和、新型有机催化剂和抗选择性好等优点。图文摘要方酸催化芳香醛、芳香胺和环酮在室温下和无溶剂反应条件下在水中的三组分曼尼希反应。该协议具有几个优点，例如良好的收率、温和的条件、新型的有机催化剂和良好的抗选择性。
• HCl-Catalyzed Stereoselective Mannich Reaction in H₂O-SDS System
  作者：Takahiko Akiyama、Keiichiro Matsuda、Kohei Fuchibe

  DOI：10.1055/s-2004-836062

  日期：——

  HCl-catalyzed Mannich reaction of cyclic ketone, aromatic aldehyde, and aromatic amine proceeded smoothly in water in the presence of SDS to afford the corresponding β-amino ketone with high anti selectivity.

  盐酸催化的环酮、芳香醛和芳香胺的曼尼希反应在 SDS 存在下于水中顺利进行，以高反选择性得到相应的δ-氨基酮。