1-isobutyl-2-methyl-4,4-diphenylpyrrolidine | 1150589-09-5

• 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-isobutyl-2-methyl-4,4-diphenylpyrrolidine
• 英文别名: 2-Methyl-1-(2-methylpropyl)-4,4-diphenylpyrrolidine；2-methyl-1-(2-methylpropyl)-4,4-diphenylpyrrolidine
• CAS: 1150589-09-5
• 化学式: C₂₁H₂₇N
• 分子量: 293.452
• InChiKey: ZQMKUEHPTFYLPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 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-pent-4-enenitrile 在 8-羟基喹啉 、 lithium aluminium tetrahydride 、 zinc(II) iodide 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醚 为溶剂， 反应 41.0h， 生成 1-isobutyl-2-methyl-4,4-diphenylpyrrolidine
  参考文献：
  名称：

  ZnI 2催化的未官能化烯烃分子内氢胺化中的配体加速

  摘要：

  研究了卤化锌促进的4-戊烯-1-胺化合物的加氢胺化反应。初步结果表明，空间因素和电子因素均对该路易斯酸促进的反应至关重要。ZnI 2给出了最有希望的结果，并且通过添加合适的配体可以进一步提高反应性。当在10 mol％的ZnI 2和8-羟基喹啉存在下于1,4-二恶烷中进行反应时，获得高达95％的分离产率。

  DOI：

  10.1016/j.tetlet.2012.06.033

文献信息

• On the Superior Activity of In(I) versus In(III) Cations Toward <i>ortho-C-</i>Alkylation of Anilines and Intramolecular Hydroamination of Alkenes
  作者：Zhilong Li、Shengwen Yang、Guillaume Thiery、Vincent Gandon、Christophe Bour

  DOI：10.1021/acs.joc.0c01585

  日期：2020.10.16

  ortho-C-alkylation of unprotected anilines with a variety of styrenes and alkenes using a univalent cationic indium(I) catalyst is reported. Mechanistic studies revealed that the reaction likely proceeds via a tandem hydroamination/Hofmann–Martius rearrangement. The high compatibility between the cationic indium(I) complex and primary anilines led us to develop an In(I)+-catalyzed hydroamination of alkenes

  一种有效的邻- Ç与各种使用一价阳离子铟苯乙烯和烯烃的未受保护的苯胺的烷基化报告（I）的催化剂。机理研究表明，该反应可能是通过串联加氢胺化/霍夫曼-马修斯重排而进行的。阳离子铟（I）配合物与伯苯胺之间的高度相容性使我们开发了使用未保护的伯和仲烯基胺进行In（I）+催化的烯烃加氢胺化反应。计算支持裸In（I）+离子的催化活性，并具有形成C–N键的外球机理和潜在的内球原金属化。
• 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。
• Trifluoroacetic acid-promoted intramolecular hydroamination of unfunctionalized olefins bearing electron-rich amino groups
  作者：Gong-Qing Liu、Bin Cui、Hui Sun、Yue-Ming Li

  DOI：10.1016/j.tet.2014.06.061

  日期：2014.9

  Trifluoroacetic acid was found to be effective in intramolecular hydroamination of unfunctionalized olefins bearing electron-rich amino groups, and the corresponding N-heterocycles were obtained in good isolated yields. The scope of the substrates was investigated, and a possible reaction mechanism was proposed. Substituents on CC double bonds and amino groups of the substrates showed drastic effects

  发现三氟乙酸可有效地对带有富电子氨基的未官能化烯烃进行分子内加氢胺化反应，并以良好的分离产率获得了相应的N-杂环。研究了底物的范围，并提出了可能的反应机理。C C双键上的取代基和底物的氨基显示出对反应过程的剧烈影响。
• Cooperative effect in organocatalytic intramolecular hydroamination of unfunctionalized olefins
  作者：Yu-Mei Wang、Ting-Ting Li、Gong-Qing Liu、Li Zhang、Lili Duan、Lin Li、Yue-Ming Li

  DOI：10.1039/c3ra47060a

  日期：——

  The cooperative effect in organocatalytic hydroamination of unfunctionalized olefins was reported. In the presence of 3-hydroxy-2-naphthoic acid, N-benzyl 4-penten-1-amines and 5-hexen-1-amines produced the intramolecular cyclization products in good isolated yields.

  报道了未官能化烯烃在有机催化加氢胺化中的协同作用。在3-羟基-2-萘甲酸的存在下，N-苄基4-戊烯-1-胺和5-己烯-1-胺以良好的分离产率产生了分子内环化产物。
• Cu(I)-Catalyzed Intramolecular Hydroamination of Unactivated Alkenes Bearing a Primary or Secondary Amino Group in Alcoholic Solvents
  作者：Hirohisa Ohmiya、Toshimitsu Moriya、Masaya Sawamura

  DOI：10.1021/ol9007712

  日期：2009.5.21

  bearing an unprotected aminoalkyl substituent in alcoholic solvents, giving pyrrolidine and piperidine derivatives in excellent yields. This system is applicable to both primary and secondary amines and tolerates a variety of functional groups.

  Cu-Xantphos系统[Cu（O- t- Bu）-Xantphos，10-15 mol％]催化未活化末端烯烃的分子内加氢胺化反应，该末端烯烃在醇溶剂中带有未保护的氨基烷基取代基，从而以优异的收率得到吡咯烷和哌啶衍生物。该系统适用于伯胺和仲胺，并且可以耐受多种官能团。