2-Methoxy-1-((S)-toluene-4-sulfinyl)-piperidine | 863211-85-2

• 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: 2-Methoxy-1-((S)-toluene-4-sulfinyl)-piperidine
• 英文别名: 2-methoxy-1-[(S)-(4-methylphenyl)sulfinyl]piperidine
• CAS: 863211-85-2
• 化学式: C₁₃H₁₉NO₂S
• 分子量: 253.365
• InChiKey: CLJBDHASKAYJHB-RUINGEJQSA-N

物化性质

• 沸点：
  389.2±52.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  48.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-Methoxy-1-((S)-toluene-4-sulfinyl)-piperidine 在 三氟甲磺酸三甲基硅酯 、 硫酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.17h， 生成 1-[(2S)-piperidin-2-yl]acetone
  参考文献：
  名称：

  Anodic oxidation of chiral sulfinylamines: a new route to highly diastereoselective α-alkylation of piperidine

  摘要：

  The anodic oxidation of some chiral non-racemic N-arylsulfinyl piperidines was investigated and for the first time alpha methoxylated sulfinyl piperidines were obtained. The so-formed compounds are equivalent of chiral N-sulfinyliminiums and used as new intermediates for the preparation of chiral alpha-substituted piperidine derivatives in good yield and diastereoselectivity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.05.123
• 作为产物：
  描述：

  menthyl p-toluenesulfinate 在 甲基溴化镁 、 N,N,N,N-tetraethylammonium tetrafluoroborate 、 potassium hydrogencarbonate 作用下， 以 四氢呋喃 为溶剂， 生成 2-Methoxy-1-((S)-toluene-4-sulfinyl)-piperidine
  参考文献：
  名称：

  Anodic oxidation of chiral sulfinylamines: a new route to highly diastereoselective α-alkylation of piperidine

  摘要：

  The anodic oxidation of some chiral non-racemic N-arylsulfinyl piperidines was investigated and for the first time alpha methoxylated sulfinyl piperidines were obtained. The so-formed compounds are equivalent of chiral N-sulfinyliminiums and used as new intermediates for the preparation of chiral alpha-substituted piperidine derivatives in good yield and diastereoselectivity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.05.123

文献信息

• Asymmetric α-Alkynylation of Piperidine <i>via </i><i>N</i>-Sulfinyliminium Salts
  作者：Serge Turcaud、Emma Sierecki、Thierry Martens、Jacques Royer

  DOI：10.1021/jo070631c

  日期：2007.6.1

  Piperidine was stereoselectively alpha-alkynylated in a four-step sequence made up of transformation to a chiral nonracemic N-sulfinylpiperidine, anodic oxidation to N-sulfinyliminium ion equivalent, alkynylation through addition of a mixed organoaluminum derivative, and final acidic deprotection of the sulfoxide. Overall yields are around 50%, and the diastereoselectivity of the nucleophilc addition was between 92 and 99% de, allowing isolation of the final product with 99% enantiomeric purity.
• Anodic oxidation of chiral sulfinylamines: a new route to highly diastereoselective α-alkylation of piperidine
  作者：Serge Turcaud、Thierry Martens、Emma Sierecki、Joëlle Pérard-Viret、Jacques Royer

  DOI：10.1016/j.tetlet.2005.05.123

  日期：2005.8

  The anodic oxidation of some chiral non-racemic N-arylsulfinyl piperidines was investigated and for the first time alpha methoxylated sulfinyl piperidines were obtained. The so-formed compounds are equivalent of chiral N-sulfinyliminiums and used as new intermediates for the preparation of chiral alpha-substituted piperidine derivatives in good yield and diastereoselectivity. (c) 2005 Elsevier Ltd. All rights reserved.