(S_S)-(E)-1-(o-chlorophenyl)-2-(p-tolylsulfinyl)-1-buten-3-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (S_S)-(E)-1-(o-chlorophenyl)-2-(p-tolylsulfinyl)-1-buten-3-one
• 英文别名: (E)-4-(2-chlorophenyl)-3-[(S)-(4-methylphenyl)sulfinyl]but-3-en-2-one
• 化学式: C₁₇H₁₅ClO₂S
• 分子量: 318.824
• InChiKey: BHHMUBLOOSVBMF-RKPWUKJMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  53.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S_S)-(E)-1-(o-chlorophenyl)-2-(p-tolylsulfinyl)-1-buten-3-one 在 乙酸铵 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 生成 4-(2-Chloro-phenyl)-2,6-dimethyl-5-(toluene-4-sulfinyl)-1,4-dihydro-pyridine-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Studies on novel and chiral 1,4-dihydropyridines. V. Hantzsch-type 1,4-dihydropyridines having a chiral sulfinyl group: Syntheses, structures, and biological activity as a calcium channel antagonist

  摘要：

  4-Aryl and 4-methyl substituted Hantzsch-type 1,4-dihydropyridines having a chiral solfinyl group as an electron-withdrawing group were successfully synthesized in an optically active form from beta-ketosulfoxides via two routes. The relationship between calcium channel antagonist activity and the structures of 4-aryl derivatives was also studied. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00155-5
• 作为产物：
  描述：

  2-氯苯甲醛 、 (+)-(R)-1-(p-tolylsulfinyl)-2-propanone 在 哌啶 作用下， 以90%的产率得到(S_S)-(E)-1-(o-chlorophenyl)-2-(p-tolylsulfinyl)-1-buten-3-one
  参考文献：
  名称：

  Novel and chiral hantzsch-type 1,4-dihydropyridines having A p-tolylsulfinyl group. Synthesis and biological activities as calcium channel antagonists.

  摘要：

  新型汉茨型 4-芳基和 4-甲基-1, 4-二氢吡啶 3 的 C-4 立体异构体均在 C-5 位上带有对甲苯磺酰基，这些立体异构体以 α-亚磺酰基烯酮 6 为起点，以光学纯度的形式高效合成，α-亚磺酰基烯酮 6 很容易从 (-)-(S)- 对甲苯磺酸盐 (4) 中获得。研究发现，C-4 处的立体化学在很大程度上决定了这些化合物作为钙通道拮抗剂的生物活性。

  DOI：

  10.1248/cpb.43.711

文献信息

• Novel and chiral hantzsch-type 1,4-dihydropyridines having A p-tolylsulfinyl group. Synthesis and biological activities as calcium channel antagonists.
  作者：Kazuyuki MIYASHITA、Masahiro NISHIMOTO、Tetsuya ISHINO、Satoshi OBIKA、Takeshi IMANISHI

  DOI：10.1248/cpb.43.711

  日期：——

  Both C-4 stereoisomers of novel Hantzch-type 4-aryl- and 4-methyl-1, 4-dihydropyridines 3 having a p-tolylsulfinyl group at C-5 were efficiently synthesized in optically pure forms starting from the α-sulfinyl enones 6 which could be easily obtained from (-)-menthyl (S)-p-tolylsulfinate (4). The stereochemistry at C-4 was found to be largely responsible for the biological activities as calcium channel antagonists of these compounds.

  新型汉茨型 4-芳基和 4-甲基-1, 4-二氢吡啶 3 的 C-4 立体异构体均在 C-5 位上带有对甲苯磺酰基，这些立体异构体以 α-亚磺酰基烯酮 6 为起点，以光学纯度的形式高效合成，α-亚磺酰基烯酮 6 很容易从 (-)-(S)- 对甲苯磺酸盐 (4) 中获得。研究发现，C-4 处的立体化学在很大程度上决定了这些化合物作为钙通道拮抗剂的生物活性。
• Studies on novel and chiral 1,4-dihydropyridines. V. Hantzsch-type 1,4-dihydropyridines having a chiral sulfinyl group: Syntheses, structures, and biological activity as a calcium channel antagonist
  作者：Kazuyuki Miyashita、Masahiro Nishimoto、Tetsuya Ishino、Hidenobu Murafuji、Satoshi Obika、Osamu Muraoka、Takeshi Imanishi

  DOI：10.1016/s0040-4020(97)00155-5

  日期：1997.3

  4-Aryl and 4-methyl substituted Hantzsch-type 1,4-dihydropyridines having a chiral solfinyl group as an electron-withdrawing group were successfully synthesized in an optically active form from beta-ketosulfoxides via two routes. The relationship between calcium channel antagonist activity and the structures of 4-aryl derivatives was also studied. (C) 1997 Elsevier Science Ltd.