1-(苯基-哌啶-1-基甲基)哌啶 | 2538-76-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: 1-(苯基-哌啶-1-基甲基)哌啶
• 英文名称: 1,1'-benzylidenedipiperidine
• 英文别名: (dipiperidinomethyl)benzene；(di(piperidin-1-yl)methyl)benzene；1,1’-(phenylmethylene)dipiperidine；1,1'-(phenylmethylene)dipiperidine；1,1’-(phenylmethylene)bis-piperidine；1,1'-phenylmethanediyl-bis-piperidine；1,1'-Benzyliden-di-piperidin；1-[phenyl(piperidin-1-yl)methyl]piperidine
• CAS: 2538-76-3
• 化学式: C₁₇H₂₆N₂
• 分子量: 258.407
• InChiKey: SBCQLLZYDKXTLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(苯基-哌啶-1-基甲基)哌啶 在 [Rh(1,2-bis(diphenylphosphanyl)butane)(COD)2]BF₄ 氢气 作用下， 以 四氢呋喃 为溶剂， 20.0 ℃ 、5.0 MPa 条件下， 反应 30.0h， 以100%的产率得到1-苄基哌啶
  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
• 作为产物：
  描述：

  哌啶 、 3-bromo-3-phenyl-3H-diazirine 反应 2.0h， 以58%的产率得到1-(苯基-哌啶-1-基甲基)哌啶
  参考文献：
  名称：

  Access to aminophenylcarbenes via diazirine exchange reactions

  摘要：

  DOI：

  10.1016/s0040-4039(01)80090-3

文献信息

• [EN] CHEMICAL PROCESSES AND COMPOUNDS DERIVED THEREFROM<br/>[FR] PROCÉDÉS CHIMIQUES ET COMPOSÉS DÉRIVÉS DE CEUX-CI
  申请人：UNIV MONASH

  公开号：WO2006012683A1

  公开（公告）日：2006-02-09

  The present invention relates to N-substituted anilines and derivatives thereof and in particular to chemical processes for the preparation of N-substituted anilines and derivatives thereof.

  本发明涉及N-取代苯胺及其衍生物，特别是用于制备N-取代苯胺及其衍生物的化学过程。
• Rediscovering aminal chemistry: copper(<scp>ii</scp>) catalysed formation under mild conditions
  作者：Juliana G. Pereira、João P. M. António、Ricardo Mendonça、Rafael F. A. Gomes、Carlos A. M. Afonso

  DOI：10.1039/d0gc01977a

  日期：——

  aldehyde lithiation. Nevertheless, the existing methodologies for their formation typically employ harsh conditions limiting their usefulness. In this work, we present an efficient and mild methodology for the preparation of aminals from aromatic aldehydes, including furanic platforms. These mild conditions allowed ease of access to a plethora of aminals and as such we set out to explore previously unaccessible

  缩醛胺中，Ñ，Ñ缩醛的类似物，已经在有机化学中进行了深入研究，特别关注杂芳醛的锂化。然而，现有的形成它们的方法通常采用苛刻的条件来限制其实用性。在这项工作中，我们提出了一种有效且温和的方法，用于从芳香醛（包括呋喃平台）制备缩醛胺。这些温和的条件使得可以轻松获得大量的动物，因此我们着手探索以前无法获得的潜在应用。通过研究各种缩醛胺的稳定性，我们能够开发出一种基于商业二胺的简单醛保护基，该保护基在精神条件下被脱保护。我们利用我们的方法和二胺树脂开发了一种清除遗传毒性醛的方案，
• SYNTHESIS OF SOME NEW SUBSTITUTED FLAVANONES AND RELATED 4-CHROMANONES BY A NOVEL SYNTHETIC METHOD
  作者：Mihail Lucian Birsa

  DOI：10.1081/scc-120001517

  日期：2002.1.1

  ABSTRACT A new heterocyclocondensation between substituted N,N,-dialkyldithiocarbamates and benzaldehyde aminals is described. The mild reaction condition, easily accessible reactants, offers a new useful synthesis of flavanones or 4-chromanones.

  摘要描述了取代的 N,N,-二烷基二硫代氨基甲酸酯和苯甲醛缩醛胺之间的一种新的杂环缩合反应。温和的反应条件，易于获得的反应物，为黄烷酮或 4-色满酮的合成提供了一种新的有用的方法。
• Spectroscopic evidence of a free-radical mechanism in the reduction of Schiff bases by formic acid
  作者：Roberto Bianchini、Claudia Forte、Giuseppe Musumarra、Calogero Pinzino、Caterina Sergi

  DOI：10.1016/s0040-4020(97)00391-8

  日期：1997.5

  The unprecedented direct detection of the free radical intermediate 7 in the reduction of Schiff bases 2 to the corresponding amines by formic acid using the EPR technique is reported. Monitoring the same reaction by NMR, line broadenings and signal shifts are observed, while the further evolution to products is triggered off by heating. No product formation or line broadening/shifts of the imine derivatives

  报道了使用EPR技术通过甲酸将席夫碱2还原为相应的胺中的自由基中间体7的空前直接检测。通过NMR监测相同的反应，观察到谱线加宽和信号移位，同时通过加热触发了产物的进一步进化。添加亚硝酸异戊酯自旋捕集器后，不会发生亚胺衍生物的产物形成或谱线变宽/移位，这会中断捕获自由基7的链过程。在亚苄基-bis的类似还原反应中也检测到单个电子物种-哌啶11由甲酸。
• Atom-efficient transition-metal-free arylation of <i>N</i>,<i>O</i>-acetals using diarylzinc reagents through Zn/Zn cooperativity
  作者：Andryj M. Borys、Jose M. Gil-Negrete、Eva Hevia

  DOI：10.1039/d1cc04137a

  日期：——

  Exploiting the cooperative action of Lewis acid Zn(C6F5)2 with diarylzinc reagents, the efficient arylation of N,O-acetals to access diarylmethylamines is reported. Reactions take place under mild reaction conditions without the need for transtion-metal catalysis. Mechanistic investigations have revealed that Zn(C6F5)2 not only acts as a Lewis acid activator, but also enables the regeneration of nucleophilic

  利用路易斯酸 Zn(C 6 F 5 ) 2与二芳基锌试剂的协同作用，报道了N , O -缩醛的有效芳基化以获得二芳基甲胺。反应在温和的反应条件下进行，不需要过渡金属催化。机理研究表明，Zn(C 6 F 5 ) 2不仅可以作为路易斯酸活化剂，而且可以使亲核 ZnAr 2物质再生，允许使用限制为 50 mol%。