4-allyl-1-tosylpiperidine | 1373334-63-4

• 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: 4-allyl-1-tosylpiperidine
• 英文别名: 4-Allyl-1-tosylpiperidine；1-(4-methylphenyl)sulfonyl-4-prop-2-enylpiperidine
• CAS: 1373334-63-4
• 化学式: C₁₅H₂₁NO₂S
• 分子量: 279.403
• InChiKey: WBXCYCSLNMJOAC-UHFFFAOYSA-N

物化性质

• 熔点：
  73-75 °C
• 沸点：
  398.7±35.0 °C(Predicted)
• 密度：
  1.116±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-[(4-甲苯)磺酰基]-4-哌啶醇 在 咪唑 、 1,3-双(二苯基膦)丙烷 、 碘 、 三苯基膦 、 cobalt(II) chloride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 4-allyl-1-tosylpiperidine
  参考文献：
  名称：

  Cobalt-Catalyzed Cross-Coupling of 3- and 4-Iodopiperidines with Grignard Reagents

  摘要：

  AbstractA cobalt‐catalyzed cross‐coupling between 3‐ and 4‐iodopiperidines and Grignard reagents is disclosed. The reaction is an efficient, cheap, chemoselective, and flexible way to functionalize piperidines. This coupling was used as the key step to realize a short synthesis of (±)‐preclamol. Some mechanistic investigations were conducted that highlight the formation of radical intermediates.

  DOI：

  10.1002/chem.201501543

文献信息

• Ni-Catalyzed Reductive Allylation of Unactivated Alkyl Halides with Allylic Carbonates
  作者：Yijing Dai、Fan Wu、Zhenhua Zang、Hengzhi You、Hegui Gong

  DOI：10.1002/chem.201102984

  日期：2012.1.16

  catalytic Ni species in the presence of an environmentally benign Zn reductant, delivering allylated alkanes (see scheme). This unprecedented approach allowed a variety of unactivated alkyl halides and substituted allylic carbonates to regioselectively afford E‐alkenes in good to excellent yields.

  两个亲电试剂的博弈：在环境无害的Zn还原剂存在下，使用催化性Ni物种可以连接两个部分带正电的sp 3碳原子，从而提供烯丙基化的烷烃（请参见方案）。这种前所未有的方法使各种未活化的烷基卤化物和取代的烯丙基碳酸酯能够选择性地以良好至极佳的收率选择性提供E-烯烃。
• Cobalt-Catalyzed Cross-Coupling of 3- and 4-Iodopiperidines with Grignard Reagents
  作者：Laurine Gonnard、Amandine Guérinot、Janine Cossy

  DOI：10.1002/chem.201501543

  日期：2015.9.1

  AbstractA cobalt‐catalyzed cross‐coupling between 3‐ and 4‐iodopiperidines and Grignard reagents is disclosed. The reaction is an efficient, cheap, chemoselective, and flexible way to functionalize piperidines. This coupling was used as the key step to realize a short synthesis of (±)‐preclamol. Some mechanistic investigations were conducted that highlight the formation of radical intermediates.