1-[(S)-1-((S)-Toluene-4-sulfinyl)-piperidin-2-yl]-propan-2-one | 863211-90-9

• 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: 1-[(S)-1-((S)-Toluene-4-sulfinyl)-piperidin-2-yl]-propan-2-one
• 英文别名: 1-[(2S)-1-[(S)-(4-methylphenyl)sulfinyl]piperidin-2-yl]propan-2-one
• CAS: 863211-90-9
• 化学式: C₁₅H₂₁NO₂S
• 分子量: 279.403
• InChiKey: OTGJGVQOEYBESP-LIRRHRJNSA-N

物化性质

• 熔点：
  50 °C
• 沸点：
  438.3±47.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  56.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-[(S)-1-((S)-Toluene-4-sulfinyl)-piperidin-2-yl]-propan-2-one 在 硫酸 作用下， 以 甲醇 为溶剂， 反应 0.17h， 以100%的产率得到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：

  1-[(S)-(4-methylphenyl)sulfinyl]piperidine 在 三氟甲磺酸三甲基硅酯 、 N,N,N,N-tetraethylammonium tetrafluoroborate 、 potassium hydrogencarbonate 作用下， 以 二氯甲烷 为溶剂， 生成 1-[(S)-1-((S)-Toluene-4-sulfinyl)-piperidin-2-yl]-propan-2-one
  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

• N-Sulfinyl Amines as a Nitrogen Source in the Asymmetric Intramolecular Aza-Michael Reaction: Total Synthesis of (−)-Pinidinol
  作者：Santos Fustero、Silvia Monteagudo、María Sánchez-Roselló、Sonia Flores、Pablo Barrio、Carlos del Pozo

  DOI：10.1002/chem.201000615

  日期：2010.8.23

  N‐Sulfinyl amines have been successfully employed as nitrogen nucleophiles for the asymmetric intramolecular aza‐Michael reaction. The synthetic strategy involves a cross‐metathesis reaction followed by the Michael‐type cyclization, either in a base‐catalyzed two‐step procedure or in a tandem fashion. The developed methodology allows access to chiral substituted pyrrolidines and piperidines bearing

  N-亚磺胺已被成功地用作不对称分子内氮杂-Michael反应的氮亲核试剂。合成策略涉及交叉易位反应，然后进行迈克尔型环化反应，可采用碱催化的两步法或串联方式进行。发达的方法学允许访问带有一个或两个立体中心的手性取代的吡咯烷和哌啶，并且该方法已用于哌啶生物碱（-）-哌啶子醇的合成。
• 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.