1-(2-phenylallyl)piperidine

• 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-(2-phenylallyl)piperidine
• 英文别名: 1-(2-phenylprop-2-enyl)piperidine；2-phenyl-3-piperidino-1-propene；1-phenyl-1-(piperidin-1-ylmethyl)ethylene
• 化学式: C₁₄H₁₉N
• 分子量: 201.312
• InChiKey: DEJRISBOQCJJFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-烯丙基哌啶 、 苯基三氟甲烷磺酸酯 在 1,1'-双(二苯基膦)二茂铁 、 palladium diacetate 三乙胺 作用下， 以 乙腈 为溶剂， 反应 20.0h， 以50%的产率得到1-(2-phenylallyl)piperidine
  参考文献：
  名称：

  Highly Regioselective Palladium-Catalyzed β-Arylation of N,N-Dialkylallylamines

  摘要：

  DOI：

  10.1021/jo000824z

文献信息

• 2-Arylallyl as a new protecting group for amines, amides and alcohols
  作者：José Barluenga、Francisco J. Fañanás、Roberto Sanz、César Marcos、José M. Ignacio

  DOI：10.1039/b414966a

  日期：——

  Amines, amides and ethers containing 2-arylallyl groups are selectively and easily deprotected with tert-butyllithium. This transformation probably involves a carbolithiation reaction of the styrenyl moiety followed by a β-elimination process.

  含有2-芳基烯丙基的胺、酰胺和醚可以通过叔丁基锂选择性且容易地进行脱保护。这一转化过程可能涉及苯乙烯基部分的车尾化反应，随后进行β-消除过程。
• Stannylated allyl carbonates as versatile building blocks for the diversity oriented synthesis of allylic amines and amides
  作者：Christian Bukovec、Uli Kazmaier

  DOI：10.1039/c0ob00945h

  日期：——

  Stannylated allylic carbonates are suitable substrates for Pd-catalyzed allylic aminations. In DMF and with [allylPdCl]2 as catalyst the stannylated allyl amines formed can be directly coupled with electrophiles according to the Stille protocol, giving rise to highly functionalized buiding blocks in excellent yields.

  钯催化的烯丙基胺化反应适用于锡烯丙基碳酸酯作为底物。在DMF中，以[allylPdCl]2为催化剂，所生成的锡烯丙基胺可直接依据Stille偶联协议与亲电试剂反应，高效获得功能化的构建单元，收率极佳。
• Scope of Aminomethylations via Suzuki−Miyaura Cross-Coupling of Organotrifluoroborates
  作者：Gary A. Molander、Paul E. Gormisky、Deidre L. Sandrock

  DOI：10.1021/jo800183q

  日期：2008.3.1

  previously reported the Suzuki−Miyaura reaction of N,N-dialkylaminomethyltrifluoroborates with aryl bromides. Herein, we report a further investigation of the scope and limitations of this palladium-catalyzed aminomethylation reaction. Aryl chlorides, iodides, and triflates coupled in good to excellent yields to give N,N-dialkylbenzylic amines. The aminomethylation of alkenyl bromides was also examined.

  我们先前报道了N，N-二烷基氨基甲基三氟硼酸酯与芳基溴化物的Suzuki-Miyaura反应。本文中，我们报告了对该钯催化的氨基甲基化反应的范围和局限性的进一步研究。芳基氯化物，碘化物和三氟甲磺酸酯以良好至优异的收率偶联，得到N，N-二烷基苄基胺。还检查了烯基溴化物的氨基甲基化。
• Copper-Catalyzed Decarboxylative Functionalization of Conjugated β,γ-Unsaturated Carboxylic Acids
  作者：Wei Zhang、Chengming Wang、Qiu Wang

  DOI：10.1021/acscatal.0c03621

  日期：2020.11.20

  Copper-catalyzed decarboxylative coupling reactions of conjugated β,γ-unsaturated carboxylic acids have been achieved for allylic amination, alkylation, sulfonylation, and phosphinoylation. This approach was effective for a broad scope of amino, alkyl, sulfonyl, and phosphinoyl radical precursors as well as various conjugated β,γ-unsaturated carboxylic acids. These reactions also feature high regioselectivity

  铜催化的共轭 β,γ-不饱和羧酸的脱羧偶联反应已用于烯丙基胺化、烷基化、磺酰化和膦酰化。这种方法对广泛的氨基、烷基、磺酰基和膦酰基自由基前体以及各种共轭 β,γ-不饱和羧酸有效。这些反应还具有区域选择性高、官能团耐受性好、操作简单等特点。机理研究表明，该反应通过铜催化亲电加成到烯烃上，然后脱羧而进行，其中涉及自由基中间体。这些见解提出了一种模块化和强大的策略，可以从容易获得且稳定的羧酸中获取多功能功能化的含烯丙基骨架。
• 8-Methylquinoline palladacycles: stable and efficient catalysts for carbon–carbon bond formation
  作者：Paul Evans、Paul Hogg、Ronald Grigg、Mohamed Nurnabi、Joanne Hinsley、Visuvanathar Sridharan、Selvaratnam Suganthan、Stewart Korn、Simon Collard、Jane E. Muir

  DOI：10.1016/j.tet.2005.06.118

  日期：2005.10

  Cyclopalladated, phosphine free, 8-methyl quinoline based complexes (2a–j) are excellent catalysts for the Heck vinylation of aryl iodides and bromides with turnover numbers of greater than 25 million observed in some cases. The catalysts are air and moisture stable.

  环钯，无膦，基于8-甲基喹啉的配合物（2a – j）是芳基碘和溴化物Heck乙烯基化的极佳催化剂，在某些情况下，其营业额大于2500万。催化剂对空气和湿气稳定。