1,2-dimethyl-4,4-diphenylpyrrolidine | 126899-80-7

• 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: 1,2-dimethyl-4,4-diphenylpyrrolidine
• 英文别名: N-methyl-2-methyl-4,4-diphenyl-pyrrolidine；1-methyl-2-methyl-4,4-diphenylpyrrolidine；N-methyl-2-methyl-5,5-diphenylpyrrolidine；1,2-dimethyl-4,4-diphenyl-pyrrolidine；1,2-Dimethyl-4,4-diphenyl-pyrrolidin；1,5-Dimethyl-3,3-diphenylpyrrolidine
• CAS: 126899-80-7
• 化学式: C₁₈H₂₁N
• 分子量: 251.371
• InChiKey: VWXFASZGGRDJAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  2,2-diphenyl-4-pentenylamine 在 bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate 、 P,P′-(9,9-二甲基-9H-氧杂蒽-4,5-二基)双[N,N,N′,N′-四乙基-亚膦酸二酰胺] 作用下， 以 1,4-二氧六环 为溶剂， 反应 7.0h， 以86%的产率得到1,2-dimethyl-4,4-diphenylpyrrolidine
  参考文献：
  名称：

  Hydroamination of Alkenes

  摘要：

  一种方法包括在反应混合物中反应氨基基团、包括铑和有机配体的组合物以及具有结构式（I）的底物。其中，R1是包括与CA键合的sp3碳原子的有机基团。R2从氢、甲基和包括与CA键合的sp3碳原子的有机基团的组中选择。R3和R4独立地从氢、甲基和包括与CB键合的sp3碳原子的有机基团的组中选择。该方法进一步包括在反应混合物中形成一个羟胺化产物。

  公开号：

  US20090156824A1

文献信息

• Efficient Generation and Increased Reactivity in Cationic Gold via Brønsted Acid or Lewis Acid Assisted Activation of an Imidogold Precatalyst
  作者：Junbin Han、Naoto Shimizu、Zhichao Lu、Hideki Amii、Gerald B. Hammond、Bo Xu

  DOI：10.1021/ol501443m

  日期：2014.7.3

  Brønsted or Lewis acid assisted activation of an imidogold precatalyst (L-Au-Pht, Pht = phthalimide) offers a superior way to generate cationic gold compared with the commonly used silver-based system. It is also broadly applicable for most common gold-catalyzed reactions. For reactions that require milder conditions, milder acids can be used for optimized efficiency.

  与常用的银基系统相比，布朗斯台德或路易斯酸辅助活化亚胺金预催化剂（L-Au-Pht，Pht = 邻苯二甲酰亚胺）提供了一种生成阳离子金的优越方法。它也广泛适用于最常见的金催化反应。对于需要温和条件的反应，可以使用温和的酸来优化效率。
• Unusual NHC–Iridium(I) Complexes and Their Use in the Intramolecular Hydroamination of Unactivated Aminoalkenes
  作者：Gellért Sipos、Arnold Ou、Brian W. Skelton、Laura Falivene、Luigi Cavallo、Reto Dorta

  DOI：10.1002/chem.201600378

  日期：2016.5.10

  N‐heterocyclic carbene (NHC) ligands with naphthyl side chains were employed for the synthesis of unsaturated, yet isolable [(NHC)Ir(cod)]+ (cod=1,5‐cyclooctadiene) complexes. These compounds are stabilised by an interaction of the aromatic wingtip that leads to a sideways tilt of the NHC−Ir bond. Detailed studies show how the tilting of such N‐heterocyclic carbenes affects the electronic shielding

  具有萘基侧链的N-杂环卡宾（NHC）配体用于合成不饱和但可分离的[（NHC）Ir（cod）] +（cod = 1,5-环辛二烯）配合物。这些化合物通过芳族翼尖的相互作用而稳定，从而导致NHC-Ir键的侧向倾斜。详细的研究表明，此类N杂环卡宾的倾斜如何影响卡宾碳原子的电子屏蔽性能，以及13 C NMR信号中的明显高场位移如何反映出这种情况。当用于分子内加氢胺化时，这些[（NHC）Ir（cod）] +在温和的反应条件下，这些物种显示出很高的催化活性。对映体纯的催化剂体系可产生具有出色对映选择性的吡咯烷。
• Inter- and Intramolecular Hydroamination of Unactivated Alkenes Catalysed by a Combination of Copper and Silver Salts: The Unveiling of a Brønstedt Acid Catalysis
  作者：Christophe Michon、Florian Medina、Frédéric Capet、Pascal Roussel、Francine Agbossou-Niedercorn

  DOI：10.1002/adsc.201000536

  日期：2010.12.17

  The combined use of a copper halide, a silver salt and a phosphane ligand was applied for the catalysis of inter- and intramolecular hydroamination of alkenes. The reactions of unactivated olefins with nitrogen substrates were investigated. Mechanistic investigations demonstrated that the catalytic system generated a Brønsted acid which appeared to be the prominent catalytic species.

  卤化铜，银盐和膦配体的组合使用被用于催化烯烃的分子间和分子内加氢胺化。研究了未活化烯烃与氮底物的反应。机理研究表明，该催化体系产生了布朗斯台德酸，该酸似乎是主要的催化物种。
• A Highly Enantioselective Zirconium Catalyst for Intramolecular Alkene Hydroamination: Significant Isotope Effects on Rate and Stereoselectivity
  作者：Kuntal Manna、Songchen Xu、Aaron D. Sadow

  DOI：10.1002/anie.201006163

  日期：2011.2.18

  Zirconium catalysts sparkle: A new chiral zirconium complex has been used to catalyze hydroamination reactions to cyclize aminopentenes into 2‐methylpyrrolidines (see scheme). The rate law supports a mechanism involving a reversible substrate–catalyst interaction that precedes the rate‐determining step. A new mechanism for zirconium‐catalyzed hydroamination has been proposed based on kinetic isotope

  锆催化剂闪闪发光：一种新的手性锆配合物已用于催化加氢胺化反应，从而将氨基戊烯环化成2-甲基吡咯烷（见方案）。速率定律支持一种在速率确定步骤之前涉及可逆的底物-催化剂相互作用的机制。基于动力学同位素效应和同位素取代对对映选择性的显着影响，提出了一种锆催化加氢胺化的新机理。
• Zirconium complexes supported by a ferrocene-based ligand as redox switches for hydroamination reactions
  作者：Yi Shen、Scott M. Shepard、Christopher J. Reed、Paula L. Diaconescu

  DOI：10.1039/c9cc01076a

  日期：——

  (thiolfan*)Zr(NEt2)2 (thiolfan* = 1,1′-bis(2,4-di-tert-butyl-6-thiophenoxy)ferrocene) and its catalytic activity for intramolecular hydroamination are reported. In situ oxidation and reduction of the metal complex results in reactivity towards different substrates. The reduced form of (thiolfan*)Zr(NEt2)2 catalyzes hydroamination reactions of primary aminoalkenes, whereas the oxidized form catalyzes hydroamination

  据报导了（thiolfan *）Zr（NEt 2）2（thiolfan * = 1,1'-双（2,4-二叔丁基-6-噻吩氧基）二茂铁）的合成及其对分子内加氢胺化的催化活性。金属配合物的原位氧化和还原导致对不同底物的反应性。（thiolfan *）Zr（NEt 2）2的还原形式催化伯氨基烯烃的加氢胺化反应，而氧化形式催化仲氨基烯烃的加氢胺化反应。