(E)-N-butyl-N-cinnamylbutan-1-amine | 1050652-07-7

• 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: (E)-N-butyl-N-cinnamylbutan-1-amine
• 英文别名: (E)-N,N-dibutylcinnamylamine；N-butyl-N-cinnamylbutan-1-amine；N,N-cinnamylbutanediamine；N-butyl-N-[(E)-3-phenylprop-2-enyl]butan-1-amine
• CAS: 1050652-07-7
• 化学式: C₁₇H₂₇N
• 分子量: 245.408
• InChiKey: TTWJFBWTJAOFAJ-JLHYYAGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  3-苯基丙-2-烯-1-醇 在 亚磷酸三苯酯 、 4-二甲氨基吡啶 、 palladium diacetate 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 0.59h， 生成 (E)-N-butyl-N-cinnamylbutan-1-amine
  参考文献：
  名称：

  低催化剂负载量的 Pd(OAc)2/P(OPh)3 体系催化的好氧烯丙基胺化

  摘要：

  Pd(OAc) 2 /P(OPh) 3组合在有氧条件下催化辻-特罗斯特型烯丙基胺化。仅当使用烯丙基磷酸盐作为亲电子试剂时，芳族和脂肪族仲胺都可通过少量催化剂体系（通常为 0.02 mol% Pd）转化为相应的烯丙基胺。其他典型的亲电子试剂，例如乙酸烯丙酯和碳酸酯，具有轻微的反应性。机械实验表明，原位形成的 Pd(0) 配合物 Pd[P(OPh) 3 ] 3是一种活性物质。

  DOI：

  10.1021/acs.joc.1c02768

文献信息

• Direct use of allylic alcohols and allylic amines in palladium-catalyzed allylic amination
  作者：Jiangyan Jing、Xiaohong Huo、Jiefeng Shen、Jingke Fu、Qinghua Meng、Wanbin Zhang

  DOI：10.1039/c7cc01069a

  日期：——

  Allylic alcohols and allylic amines were directly utilized in a Pd-catalyzed hydrogen-bond-activated allylic amination under mild reaction conditions in the absence of any additives. The cooperative action of a Pd-catalyst and a hydrogen-bonding solvent is most likely responsible for its high reactivity. The catalytic system is compatible with a variety of functional groups and can be used to prepare

  在没有任何添加剂的情况下，在温和的反应条件下，将烯丙醇和烯丙基胺直接用于钯催化的氢键活化的烯丙基胺化反应中。Pd催化剂和氢键溶剂的协同作用很可能是其高反应活性的原因。该催化体系与多种官能团相容，可用于以良好或优异的收率制备各种线性烯丙基胺。此外，该方法可以轻松地以克为单位，用于两种药物的肉桂醛和萘替芬的一步合成。
• Iridium-catalysed reductive allylic amination of α,β-unsaturated aldehydes
  作者：Liang Liu、Renshi Luo、Jinghui Tong、Jianhua Liao

  DOI：10.1039/d3ob01753b

  日期：——

  unsaturated hydrocarbons have been considered for allylic amination reactions to minimize waste production. Herein, we present an iridium-catalysed method for reductive allylic amination of α,β-unsaturated aldehydes with amines to afford N-allylic amines under air conditions. This protocol is demonstrated to provide products from many substrates (41 examples) in moderate-to-excellent yields. This synthetic

  烯丙基胺化是构建广泛存在于生物活性分子中的N-烯丙基胺的有力工具。一般来说，烯丙醇和不饱和烃已被考虑用于烯丙胺化反应，以尽量减少废物的产生。在此，我们提出了一种铱催化的方法，用于在空气条件下将 α,β-不饱和醛与胺进行还原烯丙基胺化，得到N-烯丙基胺。该方案经证明可以从许多底物（41 个示例）中提供中等至优异产量的产品。这种合成方法还体现在药物分子、光学纯产品的合成以及放大实验上。
• PROCESS FOR PRODUCING POLYMER WITH FUNCTIONAL END
  申请人：KURARAY CO., LTD.

  公开号：EP1721912A1

  公开（公告）日：2006-11-15

  An organolithium compound represented by the following general formula (i): (i) [wherein A represents a heteroatom selected among oxygen, nitrogen, sulfur, and phosphorus; Ar represents optionally substituted aryl; R1 represents C1-10 alkyl; R2 represents C1-10 alkylene; R3 represents C1-10 alkyl or a protective group for the functional group -A-H (A is a heteroatom); and when the heteroatom A is oxygen or sulfur, then m and n each is 0 or 1, provided that the sum of m and n is 1, and when the heteroatom A is nitrogen or phosphorus, then m and n each is 0, 1, or 2, provided that the sum of m and n is 2], which has not hitherto been used in anionic polymerization, is used as an anionic polymerization initiator to easily and smoothly produce a polymer having a functional group at an end.

  由以下通式(i)代表的有机锂化合物：(i) [其中 A 代表选自氧、氮、硫和磷的杂原子；Ar 代表任选取代的芳基；R1 代表 C1-10 烷基；R2 代表 C1-10 亚烷基；R3 代表 C1-10 烷基或官能团 -A-H 的保护基（A 为杂原子）；当杂原子 A 为氧或硫时，则 m 和 n 各为 0 或 1，条件是 m 和 n 之和为 1；当杂原子 A 为氮或磷时，则 m 和 n 各为 0、1 或 2，条件是 m 和 n 之和为 2]，迄今尚未用于阴离子聚合，用作阴离子聚合引发剂，可轻松顺利地生成末端具有官能团的聚合物。
• Palladium-Catalyzed Vinylation of Aminals with Simple Alkenes: A New Strategy To Construct Allylamines
  作者：Yinjun Xie、Jianhua Hu、Yanyu Wang、Chungu Xia、Hanmin Huang

  DOI：10.1021/ja310848x

  日期：2012.12.26

  A novel, highly selective palladium-catalyzed vinylation reaction for the direct synthesis of allylic amines from styrenes and aminals has been established. The utility of this method was also demonstrated by the rapid synthesis of cinnarizine from aldehydes, amines, and simple alkenes in one-pot manner. Mechanistic studies suggested that the reaction proceeds through a valuable cyclometalated Pd(II) complex generated by the oxidative addition of aminal to a Pd(0) species.
• Ruthenium-catalyzed linear selective allylic aminations of monosubstituted allyl acetates
  作者：Motoi Kawatsura、Fumio Ata、Takuya Hirakawa、Shuichi Hayase、Toshiyuki Itoh

  DOI：10.1016/j.tetlet.2008.06.002

  日期：2008.8

  The ruthenium-catalyzed highly linear selective allylic amination of monosubstituted allylic acetates with secondary amines was developed. The regioselectivity was controlled by the RU3(CO)(12)/2-DPPBA catalyst, and a linear-type aminated product was obtained as a single regioisomer. (C) 2008 Elsevier Ltd. All rights reserved.