((+/-)-(4R,5R)-2-amino-4-(4-chlorophenyl)-5-(4-methoxybenzoyl)-1-phenyl-6-thioxo-1,4,5,6-tetrahydropyridin-3-yl)(phenyl)methanone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ((+/-)-(4R,5R)-2-amino-4-(4-chlorophenyl)-5-(4-methoxybenzoyl)-1-phenyl-6-thioxo-1,4,5,6-tetrahydropyridin-3-yl)(phenyl)methanone
• 英文别名: [(3R,4R)-6-amino-5-benzoyl-4-(4-chlorophenyl)-1-phenyl-2-sulfanylidene-3,4-dihydropyridin-3-yl]-(4-methoxyphenyl)methanone
• 化学式: C₃₂H₂₅ClN₂O₃S
• 分子量: 553.081
• InChiKey: BGJJEUINBCEIHD-IXCJQBJRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.83
• 重原子数：
  39.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  72.63
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  p-Methoxybenzoyl-thioessigsaeure-anilid 、 4-氯苯甲醛 、 苯甲酰乙腈 在 三乙烯二胺 作用下， 以 乙醇 为溶剂， 反应 8.0h， 以82%的产率得到((+/-)-(4R,5R)-2-amino-4-(4-chlorophenyl)-5-(4-methoxybenzoyl)-1-phenyl-6-thioxo-1,4,5,6-tetrahydropyridin-3-yl)(phenyl)methanone
  参考文献：
  名称：

  Modulating the Reactivity of Functionalized N,S-Ketene Acetal in MCR: Selective Synthesis of Tetrahydropyridines and Thiochromeno[2,3-b]pyridines via DABCO-Catalyzed Tandem Annulation

  摘要：

  An efficient and straightforward three-component synthetic protocol was developed to synthesize 1,2,3,4-tetrahydropyridine derivatives or thiochromeno[2,3-b]pyridine derivatives from beta-aroylthioacetanilides or beta-(2-haloaroyl)thioacetanilides, aldehydes, and aroyl acetonitriles via DABCO-catalyzed tandem [3 + 2 + 1] annulation and SNAr reaction. This synthetic approach has the prominent features of high chemo-, stereo- (or enantio-), and unusual regioselectivity. In the domino processes, at least seven reactive sites were involved, and up to three covalent bonds and one functionalized pyridine ring were generated. This facile and efficient reaction is a quite general for the preparation of tetrahydropyridine derivatives or thiochromeno[2,3-b]pyridine derivatives.

  DOI：

  10.1021/jo202665q

文献信息

• Modulating the Reactivity of Functionalized <i>N</i>,<i>S</i>-Ketene Acetal in MCR: Selective Synthesis of Tetrahydropyridines and Thiochromeno[2,3-<i>b</i>]pyridines via DABCO-Catalyzed Tandem Annulation
  作者：Li-Rong Wen、Yong-Jie Shi、Guang-Yuan Liu、Ming Li

  DOI：10.1021/jo202665q

  日期：2012.5.4

  An efficient and straightforward three-component synthetic protocol was developed to synthesize 1,2,3,4-tetrahydropyridine derivatives or thiochromeno[2,3-b]pyridine derivatives from beta-aroylthioacetanilides or beta-(2-haloaroyl)thioacetanilides, aldehydes, and aroyl acetonitriles via DABCO-catalyzed tandem [3 + 2 + 1] annulation and SNAr reaction. This synthetic approach has the prominent features of high chemo-, stereo- (or enantio-), and unusual regioselectivity. In the domino processes, at least seven reactive sites were involved, and up to three covalent bonds and one functionalized pyridine ring were generated. This facile and efficient reaction is a quite general for the preparation of tetrahydropyridine derivatives or thiochromeno[2,3-b]pyridine derivatives.