(R)-2-propyl-5-methylene-1-(4-methoxy-benzenesulfonyl)-piperidine | 398137-88-7

• 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: (R)-2-propyl-5-methylene-1-(4-methoxy-benzenesulfonyl)-piperidine
• 英文别名: (2R)-1-(4-methoxyphenyl)sulfonyl-5-methylidene-2-propylpiperidine
• CAS: 398137-88-7
• 化学式: C₁₆H₂₃NO₃S
• 分子量: 309.43
• InChiKey: LQXHAHTZOZNQBL-CQSZACIVSA-N

物化性质

• 沸点：
  432.4±55.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-2-propyl-5-methylene-1-(4-methoxy-benzenesulfonyl)-piperidine 在 2,3-二巯基丁二酸 、 Na-naphthalenide 、 L-Selectride 、 臭氧 作用下， 生成 (3R,6R)-6-propylpiperidin-3-ol
  参考文献：
  名称：

  Synthesis of Functionalised Piperidines Through a [3 + 3] Cycloaddition Strategy

  摘要：

  描述了一种通过氮杂环丙烷与Pd-三甲基亚甲基复合物的[3 + 3]环加成反应制备功能化哌啶的新方法。重要的是，通过使用手性纯氮杂环丙烷（从适当的氨基酸经过三步制备），可以使相应的哌啶以手性纯形式获得。此外，还描述了这一技术在(-)-伪氢化可的因的全合成中的应用。

  DOI：

  10.1055/s-2001-17443
• 作为产物：
  描述：

  D-正缬氨酸 在 4-二甲氨基吡啶 、 palladium diacetate 、 sodium hydroxide 、 lithium aluminium tetrahydride 、 正丁基锂 、 三异丙基亚磷酸酯 、 三乙胺 、 N,N-二异丙基乙胺 、 对甲苯磺酰氯 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 28.0h， 生成 (R)-2-propyl-5-methylene-1-(4-methoxy-benzenesulfonyl)-piperidine
  参考文献：
  名称：

  Development of a [3+3] Cycloaddition Strategy toward Functionalized Piperidines

  摘要：

  This paper describes a novel route to functionalized piperidines via a formal [3+3] cycloaddition reaction of activated aziridines and palladium-trimethylenemethane (Pd-TMM) complexes. The cycloaddition reaction generally proceeds enantiospecifically with ring opening at the least hindered site of the aziridine. Therefore, readily available enantiomerically pure 2-substituted aziridines can be utilized to prepare enantiomerically pure 2-substituted piperidines in good to excellent yield. The N-substituent on the aziridine proved to be crucial to the success of this reaction with only 4-toluenesulfonyl (Ts) and 4-methoxybenzenesulfonyl (PMBS) aziridines permitting smooth cycloaddition to take place. Additionally, spirocyclic aziridines have been found to participate in the [3+3] cycloaddition reaction, whereas 2,3-disubstituted aziridines can be applied to provide fused bicyclic piperidines, albeit in low yield.

  DOI：

  10.1021/jo030002c

文献信息

• Synthesis of Functionalised Piperidines Through a [3 + 3] Cycloaddition Strategy
  作者：Simon J. Hedley、Wesley J. Moran、Alexander H. G. P. Prenzel、David A. Price、Joseph P. A. Harrity

  DOI：10.1055/s-2001-17443

  日期：——

  A novel approach to functionalised piperidines is described through a [3 + 3] cycloaddition reaction of aziridines with Pd-trimethylenemethane complexes. Importantly, the employment of enantiomerically pure aziridines (prepared in three steps from the appropriate amino acids) allows the corresponding piperidines to be furnished in enantiomerically pure form. Additionally, the application of this technique in the total synthesis of (-)-pseudoconhydrine is described.

  描述了一种通过氮杂环丙烷与Pd-三甲基亚甲基复合物的[3 + 3]环加成反应制备功能化哌啶的新方法。重要的是，通过使用手性纯氮杂环丙烷（从适当的氨基酸经过三步制备），可以使相应的哌啶以手性纯形式获得。此外，还描述了这一技术在(-)-伪氢化可的因的全合成中的应用。
• Development of a [3+3] Cycloaddition Strategy toward Functionalized Piperidines
  作者：Simon J. Hedley、Wesley J. Moran、David A. Price、Joseph P. A. Harrity

  DOI：10.1021/jo030002c

  日期：2003.5.1

  This paper describes a novel route to functionalized piperidines via a formal [3+3] cycloaddition reaction of activated aziridines and palladium-trimethylenemethane (Pd-TMM) complexes. The cycloaddition reaction generally proceeds enantiospecifically with ring opening at the least hindered site of the aziridine. Therefore, readily available enantiomerically pure 2-substituted aziridines can be utilized to prepare enantiomerically pure 2-substituted piperidines in good to excellent yield. The N-substituent on the aziridine proved to be crucial to the success of this reaction with only 4-toluenesulfonyl (Ts) and 4-methoxybenzenesulfonyl (PMBS) aziridines permitting smooth cycloaddition to take place. Additionally, spirocyclic aziridines have been found to participate in the [3+3] cycloaddition reaction, whereas 2,3-disubstituted aziridines can be applied to provide fused bicyclic piperidines, albeit in low yield.