1-(2-phenylpropyl)piperidine | 36794-50-0

• 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-phenylpropyl)piperidine
• CAS: 36794-50-0
• 化学式: C₁₄H₂₁N
• 分子量: 203.327
• InChiKey: GPGAPOXPDQJNTJ-UHFFFAOYSA-N

物化性质

• 沸点：
  133-135 °C(Press: 12 Torr)
• 密度：
  0.9546 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  2-Phenyl-1-piperidin-1-yl-propan-1-ol 在 [Rh(1,2-bis(diphenylphosphanyl)butane)(COD)2]BF₄ 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、5.0 MPa 条件下， 反应 308.0h， 生成 1-(2-phenylpropyl)piperidine
  参考文献：
  名称：

  A Scrutiny on the Reductive Amination of Carbonyl Compounds Catalyzed by Homogeneous Rh(I) Diphosphane Complexes

  摘要：

  The reductive amination of a series of aldehydes with secondary amines and H-2 in the presence of a homogeneous Rh-diphosphane catalyst was studied in order to establish a general mechanism of this reaction and to identify conditions for the improvement of the amine/alcohol ratio in the product. Several possible intermediates as constituents of changing equilibria like half-aminals. N,O-acetals and aminals were observed in the reaction mixture by means of H-1 NMR spectroscopy. In individual trials, these compounds could be successfully hydrogenated under the conditions applied for reductive amination (50 bar H-2 pressure, MeOH). Some evidence is accumulated that half-aminals and N,O-acetals might be key intermediates of the reductive amination. Moreover, it was found that the formation of the undesired product alcohol is likely based on the reduction of the starting carbonyl compound. However, due to numerous equilibria consisting of several intermediates, general conclusions are hard to be drawn. Proof will be given that, in several cases, the efficiency of the reductive amination of aliphatic aldehydes can be significantly improved by prehydrogenation of the cationic [Rh(dppb)(COD)](+) complex.

  DOI：

  10.1002/1615-4169(200202)344:2<200::aid-adsc200>3.0.co;2-4

文献信息

• Method for producing amines by homogeneously catalyzed reductive amination of carbonyl compounds
  申请人：Riermeier Thomas

  公开号：US06884887B1

  公开（公告）日：2005-04-26

  The invention relates to the preparation of chiral or achiral amines by reaction of aldehydes or ketones with ammonia or primary or secondary amines in the presence of hydrogen and in the presence of homogeneous metal catalysts under mild conditions. Metal catalysts which can be used are complexes of late transition metals with chiral or achiral phosphorus-containing ligands.

  该发明涉及在温和条件下，在氢气存在下和均相金属催化剂存在下，通过醛或酮与氨或一级或二级胺的反应制备手性或无手性胺。可使用的金属催化剂是含手性或无手性磷配体的后过渡金属络合物。
• Highly efficient and eco-friendly synthesis of tertiary amines by reductive alkylation of aldehydes with secondary amines over a Pt nanowires catalyst
  作者：Junjie Wu、Shuanglong Lu、Danhua Ge、Hongwei Gu

  DOI：10.1039/c5ra12299f

  日期：——

  A highly efficient and environmentally friendly method for the synthesis of tertiary amines by direct interaction of aldehydes with secondary amines was reported over a Pt NWs catalyst under mild reaction conditions.

  一种高效环保的方法报告了在温和反应条件下，通过醛与二级胺的直接作用在Pt NWs催化剂下合成三级胺。
• On the reductive amination of aldehydes and ketones catalyzed by homogeneous Rh(i) complexes
  作者：Vitali I. Tararov、Renat Kadyrov、Armin Börner、Thomas H. Riermeier

  DOI：10.1039/b005777k

  日期：——

  The homogeneously catalyzed reductive amination of aldehydes and ketones under smooth conditions is reported, showing for the first time, that Rh(I) catalysts based on chelating diphosphines and diphosphinites can be advantageously employed for this reaction, even for the production of chiral amino acid derivatives.

  报道了在平滑条件下均相催化的醛和酮的还原胺化反应，首次表明基于螯合二膦和二亚膦酸盐的 Rh(I) 催化剂可有利地用于该反应，甚至用于生产手性氨基酸衍生物.
• Base-Catalyzed Anti-Markovnikov Hydroamination of Vinylarenes – Scope, Limitations and Computational Studies
  作者：Patricia Horrillo-Martínez、Kai C. Hultzsch、Adrià Gil、Vicenç Branchadell

  DOI：10.1002/ejoc.200700147

  日期：2007.7

  The hydroamination of vinylarenes with primary and secondary amines was studied with catalytic amounts as low as 2 mol-% of LiN(SiMe3)2/TMEDA. Reactions proceeded readily at 120 °C in the absence of solvent to give selective anti-Markovnikov addition. Slow addition was observed at 25 °C with either electron-deficient p-chlorostyrene or secondary cyclic amines such as pyrrolidine, piperidine, or morpholine

  使用低至 2 mol% 的 LiN(SiMe3)2/TMEDA 的催化量研究了乙烯基芳烃与伯胺和仲胺的加氢胺化。在没有溶剂的情况下，反应在 120 °C 下很容易进行，以提供选择性的抗马尔科夫尼科夫加成物。在 25 °C 下观察到使用缺电子对氯苯乙烯或仲环胺（如吡咯烷、哌啶或吗啉）缓慢添加。伯胺易于进行二次加氢胺化反应以形成叔胺副产物。单（加氢胺化）产物的选择性可以用两倍过量的胺来提高。与 LiN(SiMe3)2 相比，KN(SiMe3)2 显示出更高的催化活性，但选择性更低，导致不希望的 C-H 活化副产物。用密度泛函理论研究了锂催化加氢胺化的机理和TMEDA的影响。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
• Hydroaminomethylation with Novel Rhodium–Carbene complexes: An Efficient Catalytic Approach to Pharmaceuticals
  作者：Moballigh Ahmed、Cathleen Buch、Lucie Routaboul、Ralf Jackstell、Holger Klein、Anke Spannenberg、Matthias Beller

  DOI：10.1002/chem.200601155

  日期：2007.2.2

  3-dimesitylimidazole-2-ylidenes the novel [RhCl(cod)(carbene)] complexes 1-5 have been synthesized, characterized, and tested in the hydroaminomethylation of aromatic olefins. The influence of different ligands and reaction parameters on the catalytic activity was investigated in detail applying 1,1-diphenylethylene and piperidine as a model system. The scope and limitations of the novel catalysts is shown in the

  从[Rh（cod）Cl}（2）]和1,3-二甲基咪唑-2-亚烷基开始，已经合成，表征和测试了新型[RhCl（cod）（carbene）]配合物1-5芳族烯烃。以1，1-二苯基乙烯和哌啶为模型体系，详细研究了不同配体和反应参数对催化活性的影响。在制备16种具有生物活性的1-氨基-3,3-二芳基丙烯中显示了新型催化剂的范围和局限性。通常，获得了高的化学和区域选择性以及所需产物的良好产率。