ethyl 1-methyl-3-(phenylsulfinyl)piperidine-3-carboxylate | 470700-28-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: ethyl 1-methyl-3-(phenylsulfinyl)piperidine-3-carboxylate
• 英文别名: Ethyl 3-(benzenesulfinyl)-1-methylpiperidine-3-carboxylate；ethyl 3-(benzenesulfinyl)-1-methylpiperidine-3-carboxylate
• CAS: 470700-28-8
• 化学式: C₁₅H₂₁NO₃S
• 分子量: 295.403
• InChiKey: PRLDLVHDOJVSFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  65.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 1-methyl-3-(phenylsulfinyl)piperidine-3-carboxylate 在 溶剂黄146 作用下， 反应 22.0h， 以64%的产率得到1-甲基-1,2,5,6-四氢烟酸乙酯
  参考文献：
  名称：

  Intriguing Influence of the Solvent on the Regioselectivity of Sulfoxide Thermolysis in β-Amino-α-sulfinyl Esters

  摘要：

  The sulfoxide thermolysis of the diastereoisomeric methyl (3R,4aS, 10R)-6-methoxy-1-methyl-3-(phenylisulfinyl)-1,2,3,4,4a,5,10,10a-oct hydrobenzo[g]quinoline-3-carboxylates 3a and Yb in toluene yields, by loss of benzenesulfenic acid, an almost 1 : 1 mixture of the vinylogous urethane 2b and the isomeric alpha-aminoethyl enoate 2a. When this elimination is performed in acetic acid, the enoate 2a is formed rather selectively. The same solvent effects on the regioselectivity of the elimination of benzenesulfenic acid are observed with a simple sulfoxide of ethyl piperidine-3-carboxylate (7).

  DOI：

  10.1002/1522-2675(200205)85:5<1399::aid-hlca1399>3.0.co;2-r
• 作为产物：
  描述：

  3-哌啶甲酸乙酯 在 palladium on activated charcoal Oxone 、 正丁基锂 、 氢气 、 溶剂黄146 、 二异丙胺 作用下， 以 四氢呋喃 、 乙醇 、 水 、 丙酮 为溶剂， 反应 0.5h， 生成 ethyl 1-methyl-3-(phenylsulfinyl)piperidine-3-carboxylate
  参考文献：
  名称：

  Intriguing Influence of the Solvent on the Regioselectivity of Sulfoxide Thermolysis in β-Amino-α-sulfinyl Esters

  摘要：

  The sulfoxide thermolysis of the diastereoisomeric methyl (3R,4aS, 10R)-6-methoxy-1-methyl-3-(phenylisulfinyl)-1,2,3,4,4a,5,10,10a-oct hydrobenzo[g]quinoline-3-carboxylates 3a and Yb in toluene yields, by loss of benzenesulfenic acid, an almost 1 : 1 mixture of the vinylogous urethane 2b and the isomeric alpha-aminoethyl enoate 2a. When this elimination is performed in acetic acid, the enoate 2a is formed rather selectively. The same solvent effects on the regioselectivity of the elimination of benzenesulfenic acid are observed with a simple sulfoxide of ethyl piperidine-3-carboxylate (7).

  DOI：

  10.1002/1522-2675(200205)85:5<1399::aid-hlca1399>3.0.co;2-r

文献信息

• Intriguing Influence of the Solvent on the Regioselectivity of Sulfoxide Thermolysis in β-Amino-α-sulfinyl Esters
  作者：Markus Bänziger、Solange Klein、Grety Rihs

  DOI：10.1002/1522-2675(200205)85:5<1399::aid-hlca1399>3.0.co;2-r

  日期：2002.5

  The sulfoxide thermolysis of the diastereoisomeric methyl (3R,4aS, 10R)-6-methoxy-1-methyl-3-(phenylisulfinyl)-1,2,3,4,4a,5,10,10a-oct hydrobenzo[g]quinoline-3-carboxylates 3a and Yb in toluene yields, by loss of benzenesulfenic acid, an almost 1 : 1 mixture of the vinylogous urethane 2b and the isomeric alpha-aminoethyl enoate 2a. When this elimination is performed in acetic acid, the enoate 2a is formed rather selectively. The same solvent effects on the regioselectivity of the elimination of benzenesulfenic acid are observed with a simple sulfoxide of ethyl piperidine-3-carboxylate (7).