N-cinnamyldiphenylamine

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-cinnamyldiphenylamine
• 英文别名: N-[(E)-3-phenyl-2-propenyl]diphenylamine；N-cinnamyl-N-phenylaniline；N-phenyl-N-[(E)-3-phenylprop-2-enyl]aniline
• 化学式: C₂₁H₁₉N
• 分子量: 285.389
• InChiKey: UUVIOVZOHUOQIG-JLHYYAGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 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：

  烯丙苯 、 二苯胺 在 palladium(II) trifluoroacetate 作用下， 以 2,3,4-三氟甲苯 为溶剂， 40.0 ℃ 、1.01 MPa 条件下， 反应 24.0h， 以75%的产率得到N-cinnamyldiphenylamine
  参考文献：
  名称：

  Pd（OCOCF 3）2 / NPMoV / O 2体系催化简单芳烃与二芳基胺的分子间需氧氧化烯丙基胺化

  摘要：

  分子间有氧氧化用简单的胺类如二苯胺简单烷基烯烃的烯丙基胺化诱导通过Pd（OCOCF 3）2 / NPMoV催化系统，导致相应的（ê）-allylamines以良好产率，并通过（η的形成选择性3-烯丙基）三氟乙酸钯（II）可能是关键的中间体。

  DOI：

  10.1021/ol100292g

文献信息

• C–N Bond Formation from Allylic Alcohols via Cooperative Nickel and Titanium Catalysis
  作者：S. Hadi Nazari、Norma Tiempos-Flores、Kelton G. Forson、Jefferson E. Bourdeau、David J. Michaelis

  DOI：10.1021/acs.joc.8b01474

  日期：2018.9.7

  Amination of allylic alcohols is facilitated via cooperative catalysis. Catalytic Ti(O-i-Pr)4 is shown to dramatically increase the rate of nickel-catalyzed allylic amination, and mechanistic experiments confirm activation of the allylic alcohol by titanium. Aminations of primary and secondary allylic alcohols are demonstrated with a variety of amine nucleophiles. Diene-containing substrates also cyclize

  通过协同催化促进烯丙基醇的胺化。催化性Ti（O - Pr）4可以显着提高镍催化的烯丙基胺化的速率，并且机械实验证实钛可以活化烯丙基醇。用各种胺亲核试剂证明伯和仲烯丙基醇的胺化。含二烯的底物在胺化之前还会环化在烯丙基镍中间体上，生成碳环胺产物。此串联过程仅在我们的协同催化系统下才能实现。
• Palladium(0)-Catalyzed Allylation of Highly Acidic and Nonnucleophilic Anilines. The Origin of Stereochemical Scrambling When Using Allylic Carbonates
  作者：Marcial Moreno-Mañas、Lurdes Morral、Roser Pleixats

  DOI：10.1021/jo980209j

  日期：1998.9.1

  nitroanilines are efficiently allylated under palladium catalysis using allyl carbonates as allylating reagents. A stereochemical study of the reactions of ethyl cis-5-methyl-2-cyclohexenylcarbonate with 4-nitro- and 2,4-dinitroaniline was performed. Bidentate phosphines as stabilizing ligands gave clean retention of configuration whereas triphenylphosphine permitted cis-trans isomerization of the allylic carbonate

  酸性苯胺（如二苯胺，吩噻嗪和硝基苯胺）在钯催化下使用碳酸烯丙酯作为烯丙基化试剂可以有效地烯丙基化。进行了立体化学研究顺式5-甲基-2-环己烯基碳酸乙酯与4-硝基和2,4-二硝基苯胺的反应。二齿膦作为稳定的配体，使构型保持清晰，而三苯膦则允许烯丙基碳酸酯的顺反异构化，烯丙基化反应发生在Curtin-Hammet预平衡条件下。
• Direct Allylic Amination of Allylic Alcohol Catalyzed by Palladium Complex Bearing Phosphine–Borane Ligand
  作者：Goki Hirata、Hideaki Satomura、Hidenobu Kumagae、Aika Shimizu、Gen Onodera、Masanari Kimura

  DOI：10.1021/acs.orglett.7b03023

  日期：2017.11.17

  The direct electrophilic, nucleophilic, and amphiphilic allylations of allylic alcohol by use of a palladium catalyst and organometallic reagents such as organoborane and organozinc has been developed. The phosphine–borane compound works as the effective ligand for palladium-catalyzed direct allylic amination of allylic alcohol. Thus, with secondary amines, the reaction was completed in only 1 h, even

  已经开发了通过使用钯催化剂和有机金属试剂例如有机硼烷和有机锌的烯丙基醇的直接亲电子，亲核和两亲烯丙基化。膦-硼烷化合物可作为钯催化的烯丙基醇直接烯丙基胺化的有效配体。因此，使用仲胺，即使在室温下，反应也仅需1小时即可完成。
• Palladium-Catalyzed Allylation of Acidic and Less Nucleophilic Anilines Using Allylic Alcohols Directly
  作者：Yi-Chun Hsu、Kim-Hong Gan、Shyh-Chyun Yang

  DOI：10.1248/cpb.53.1266

  日期：——

  activation of C-O bonds in allylic alcohols by palladium complexes has been accelerated by carrying out the reactions in the presence of titanium(IV) isoproxide and 4 A molecular sieves. The acidic and less nucleophilic anilines such as diphenylamine, phenothiazine, 4-cyanoaniline, and nitroanilines are efficiently allylated under palladium catalysis using allylic alcohols as allylating reagents.

  通过在异丙氧基钛（IV）和4 A分子筛的存在下进行反应，可以加快钯络合物在烯丙醇中CO键的直接活化。酸性和较少亲核性的苯胺，如二苯胺，吩噻嗪，4-氰基苯胺和硝基苯胺，在钯催化下使用烯丙醇作为烯丙基化试剂可以有效地烯丙基化。
• 15-Membered Triolefinic Macrocycles − Catalytic Role of (E,E,E)-1,6,11-Tris(arenesulfonyl)-1,6,11-triazacyclopentadeca-3,8,13-triene Complexes of Palladium(0) in the Presence of Phosphanes
  作者：Marcial Moreno-Mañas、Roser Pleixats、Jan Spengler、Carole Chevrin、Boris Estrine、Sandrine Bouquillon、Françoise Hénin、Jacques Muzart、Anna Pla-Quintana、Anna Roglans

  DOI：10.1002/ejoc.200390029

  日期：2003.1

  The palladium(0) complexes of (E,E,E)-1,6,11-tris(arenesulfonyl)-1,6,11-triazacyclopentadeca-3,8,13-trienes deliver palladium to phosphanes with the generation of high concentrations of catalytically active species such as Pd(PPh3)2. After oxidation of the phosphanes, the palladium is reincorporated into the macrocycle, thus avoiding agglomeration and precipitation. These conclusions were reached by

  (E,E,E)-1,6,11-tris(arenesulfonyl)-1,6,11-triazacyclopentadeca-3,8,13-trienes 的钯 (0) 络合物将钯传递给磷烷，生成高Pd(PPh3)2 等催化活性物质的浓度。磷烷氧化后，钯重新结合到大环中，从而避免团聚和沉淀。这些结论是通过 31P NMR、19F NMR 和调聚和 Tsuji-Trost 反应的电喷雾电离质谱研究得出的。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)