N-cinnamylcyclohexanamine | 107261-83-6

• 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: N-cinnamylcyclohexanamine
• 英文别名: N-[(2E)-3-phenylprop-2-en-1-yl]cyclohexanamine；N-[(E)-3-phenylprop-2-enyl]cyclohexanamine
• CAS: 107261-83-6
• 化学式: C₁₅H₂₁N
• 分子量: 215.338
• InChiKey: XSNNOGOAEQYKAL-JXMROGBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 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：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-cinnamylcyclohexanamine 在 fac-tris(2-phenylpyridinato-N,C2')iridium(III) 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 16.0h， 生成 tert-butyl (Z)-cyclohexyl(3-phenylallyl)carbamate
  参考文献：
  名称：

  Facile Synthesis of Z-Alkenes via Uphill Catalysis

  摘要：

  Catalytic access to thermodynamically less stable Z-alkenes has recently received considerable attention. These approaches have relied upon kinetic control of the reaction to arrive at the thermodynamically less stable geometrical isomer. Herein, we present an orthogonal approach which proceeds via photochemically catalyzed isomerization of the thermodynamic E-alkene to the less stable Z-isomer which occurs via a photochemical pumping mechanism. We consider two potential mechanisms. Importantly, the reaction conditions are mild, tolerant, and operationally simple and will be easily implemented.

  DOI：

  10.1021/ja5019749
• 作为产物：
  描述：

  3-苯基丙-2-烯-1-醇 在 氢溴酸 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 17.0h， 生成 N-cinnamylcyclohexanamine
  参考文献：
  名称：

  Facile Synthesis of Z-Alkenes via Uphill Catalysis

  摘要：

  Catalytic access to thermodynamically less stable Z-alkenes has recently received considerable attention. These approaches have relied upon kinetic control of the reaction to arrive at the thermodynamically less stable geometrical isomer. Herein, we present an orthogonal approach which proceeds via photochemically catalyzed isomerization of the thermodynamic E-alkene to the less stable Z-isomer which occurs via a photochemical pumping mechanism. We consider two potential mechanisms. Importantly, the reaction conditions are mild, tolerant, and operationally simple and will be easily implemented.

  DOI：

  10.1021/ja5019749

文献信息

• Allylic Amination of Alkenes with Iminothianthrenes to Afford Alkyl Allylamines
  作者：Qiang Cheng、Junting Chen、Songyun Lin、Tobias Ritter

  DOI：10.1021/jacs.0c08248

  日期：2020.10.14

  Allylic C–H amination is currently accomplished with (sulfon)amides or carbamates. Here we show the first allylic amination that can directly afford alkyl allylamines, enabled by the reactivity of thianthrene-based nitrogen sources that can be prepared from primary amines in a single step.

  烯丙基 C-H 胺化目前是用（磺）酰胺或氨基甲酸酯完成的。在这里，我们展示了第一个可以直接提供烷基烯丙胺的烯丙基胺化，这是由基于噻蒽的氮源的反应性实现的，该氮源可以在一个步骤中从伯胺制备。
• An Efficient and Convenient Palladium Catalyst System for the Synthesis of Amines from Allylic Alcohols
  作者：Debasis Banerjee、Rajenahally V. Jagadeesh、Kathrin Junge、Henrik Junge、Matthias Beller

  DOI：10.1002/cssc.201200247

  日期：2012.10

  A novel catalyst system for efficient amination of allylic alcohols with aryl and alkyl amines is presented. By applying a convenient combination consisting of Pd(OAc)2/1,10‐phenanthroline, a variety of allylic alcohols reacted smoothly to give the corresponding secondary and tertiary amines in good to excellent yields with high regioselectivity. The usefulness of our protocol is demonstrated in the

  提出了一种新颖的催化剂体系，用于用芳基和烷基胺有效地烯丙基醇的胺化。通过应用由Pd（OAc）2 / 1,10-菲咯啉组成的便捷组合，各种烯丙基醇可以平滑反应，从而以高至极好的收率和良好的区域选择性提供相应的仲胺和叔胺。抗真菌药物萘替芬和钙通道阻滞剂氟那利嗪的一步合成证明了我们方案的有效性。
• Direct Use of Allylic Alcohols for Platinum-Catalyzed Monoallylation of Amines
  作者：Masaru Utsunomiya、Yoshiki Miyamoto、Junji Ipposhi、Takashi Ohshima、Kazushi Mashima

  DOI：10.1021/ol071365s

  日期：2007.8.1

  A new direct catalytic amination of allylic alcohols promoted by the combination of platinum and a large bite-angle ligand DPEphos was developed in which the allylic alcohol was effectively converted to a pi-allylplatinum intermediate without the use of an activating reagent. The use of the DPEphos ligand was essential for obtaining high catalyst activity and high monoallylation selectivity of primary

  通过铂和大咬角配体DPEphos的结合促进了新的烯丙基醇的直接催化胺化反应，其中不使用活化剂就将烯丙基醇有效地转化为π-烯丙基铂中间体。DPEphos配体的使用对于获得高催化剂活性和伯胺的高单烯丙基化选择性至关重要，从而可以形成多种单烯丙基化产物，收率良好。
• Palladium-Catalyzed Regioselective Arylation of Unprotected Allylamines
  作者：Vinod G. Landge、Justin M. Maxwell、Pratibha Chand-Thakuri、Mohit Kapoor、Evan T. Diemler、Michael C. Young

  DOI：10.1021/jacsau.0c00003

  日期：2021.1.25

  prevalent in a variety of biologically relevant structures, yet there are few catalytic approaches to their synthesis, and none involving the free amine. Herein, we describe a simple protocol for the arylation of cinnamylamines and the diarylation of terminal allylamines to generate a diverse group of 3,3-diarylallylamine products using a PdII precatalyst. Key features of the method are the ability to access

  由于可能发生氧化等副反应，钯催化的游离胺的有机金属转化通常不成功。然而，从这些反应中提供游离胺产物的能力对于提高这些过程的实用性和可持续性非常重要，特别是对于发挥它们作为医药和农业化学试剂的潜力。值得注意的是，3,3-二芳基烯丙胺基序普遍存在于各种生物学相关结构中，但其合成的催化方法很少，而且没有涉及游离胺。在此，我们描述了一种使用 Pd II预催化剂对肉桂胺进行芳基化和对末端烯丙胺进行二芳基化以生成多种 3,3-二芳基烯丙胺产品的简单方案。该方法的主要特点是能够获得相对温和的条件，有利于广泛的底物范围以及末端烯丙胺底物的直接二芳基化。此外，还包括一些复杂的和治疗相关的分子来证明转化的效用。
• Palladium-Catalyzed Oxidative Amination of Unactivated Olefins with Primary Aliphatic Amines
  作者：Mingda Li、Yangbin Jin、Yupeng Chen、Wanqing Wu、Huanfeng Jiang

  DOI：10.1021/jacs.3c02114

  日期：2023.5.3

  Direct coupling of unactivated olefins with primary alkylamines is considered to be an efficient but unknown method for the construction of complex amines. Herein we report a catalytic intermolecular oxidative amination of unactivated olefins with primary aliphatic amines based on the combination of a palladium catalyst, a bidentate phosphine ligand, and duroquinone. A range of secondary allylic amines

  未活化的烯烃与伯烷基胺的直接偶联被认为是构建复杂胺的有效但未知的方法。在此，我们报道了基于钯催化剂、双齿膦配体和二氢醌的组合，未活化烯烃与脂肪族伯胺的催化分子间氧化胺化。以良好的收率获得了一系列仲烯丙胺，具有出色的区域选择性和立体选择性。机械控制实验表明，反应通过烯丙基 C(sp 3 )–H 活化和亲核胺化进行。通过药物分子的后期修改和简化合成，进一步证明了该协议的实用性。