(S_S,4R)-1-(p-methoxyphenyl)-4-methyl-6-phenyl-5-(p-tolylsulfinyl)-5,6-dehydropiperidin-2-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S_S,4R)-1-(p-methoxyphenyl)-4-methyl-6-phenyl-5-(p-tolylsulfinyl)-5,6-dehydropiperidin-2-one
• 化学式: C₂₆H₂₅NO₃S
• 分子量: 431.555
• InChiKey: BPTWSHLIJHBHCY-KKIUXKEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.55
• 重原子数：
  31.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  4-甲氧基-N-（1-苯基亚乙基）苯甲胺 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 生成 (S_S,4R)-1-(p-methoxyphenyl)-4-methyl-6-phenyl-5-(p-tolylsulfinyl)-5,6-dehydropiperidin-2-one
  参考文献：
  名称：

  Diastereoselective synthesis of 4-substituted 5-(p-tolylsulfinyl)-5,6-dehydropiperidin-2-ones. A new approach to methyl l-(2S,4S)-4-methyl-6-oxopipecolate

  摘要：

  The sulfoxide-mediated diastereoselective Michael reaction of homochiral alpha-sulfinylketimines 1a-d and beta-substituted ene esters 2a-d (Hua's reaction) was explored. Straight forward cyclization of the open-chain adducts take place under the reaction conditions to provide the 4-substituted 5-(p-tolylsulfinyl)-5,6-dehydropiperidin-2-ones 3 and 7-12, whose stereochemistry is formed in the prior step. Furthermore. the role of the metal ion of the aza-enolate reagents and the steric demands of the O-alkyl ester group have been examined. It seems that the anti-diastereoselectivity depends on metal chelation by the oxygen of the ester as well as the oxygen of the sulfinyl group and the nitrogen in the aza-enolate ((Z)-configuration). In addition, the synthesis of methyl L-(2S,4S)-4-methyl-6-oxopipecolate has been achieved from the suitably functionalized 2-sulfinylketimine 1a (five steps; overall yield: 53-65%). (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00553-5

文献信息

• Diastereoselective synthesis of 4-substituted 5-(p-tolylsulfinyl)-5,6-dehydropiperidin-2-ones. A new approach to methyl l-(2S,4S)-4-methyl-6-oxopipecolate
  作者：Hassan Acherki、Carlos Alvarez-Ibarra、Alfonso de Dios、Marta Gutiérrez、Marı́a L. Quiroga

  DOI：10.1016/s0957-4166(01)00553-5

  日期：2001.12

  The sulfoxide-mediated diastereoselective Michael reaction of homochiral alpha-sulfinylketimines 1a-d and beta-substituted ene esters 2a-d (Hua's reaction) was explored. Straight forward cyclization of the open-chain adducts take place under the reaction conditions to provide the 4-substituted 5-(p-tolylsulfinyl)-5,6-dehydropiperidin-2-ones 3 and 7-12, whose stereochemistry is formed in the prior step. Furthermore. the role of the metal ion of the aza-enolate reagents and the steric demands of the O-alkyl ester group have been examined. It seems that the anti-diastereoselectivity depends on metal chelation by the oxygen of the ester as well as the oxygen of the sulfinyl group and the nitrogen in the aza-enolate ((Z)-configuration). In addition, the synthesis of methyl L-(2S,4S)-4-methyl-6-oxopipecolate has been achieved from the suitably functionalized 2-sulfinylketimine 1a (five steps; overall yield: 53-65%). (C) 2002 Elsevier Science Ltd. All rights reserved.