N-(1',1'-dimethylallyl)-4-methylaniline | 60173-65-1

• 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-(1',1'-dimethylallyl)-4-methylaniline
• 英文别名: (1,1-dimethylallyl)-p-tolylamine；p-Methyl-N-(α,α-dimethylallyl)anilin；4-methyl-N-(2-methylbut-3-en-2-yl)aniline
• CAS: 60173-65-1
• 化学式: C₁₂H₁₇N
• 分子量: 175.274
• InChiKey: VVVDWSMRKICNST-UHFFFAOYSA-N

物化性质

• 沸点：
  260.0±9.0 °C(Predicted)
• 密度：
  0.940±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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-(1',1'-dimethylallyl)-4-methylaniline 在 吡啶 、 18-冠醚-6 、 potassium carbonate 、 对甲苯磺酸 作用下， 以 水 、 氯苯 、 乙腈 为溶剂， 反应 13.5h， 生成
  参考文献：
  名称：

  Domino Aryne Annulation via a Nucleophilic–Ene Process

  摘要：

  1,2-Benzdiyne equivalents possess the unique property that they can react with two arynophiles through iteratively generated 1,2- and 2,3-aryne intermediates. Upon rational modification on the second leaving group of these aryne precursors, a domino aryne annulation approach was developed through a nucleophilic-ene reaction sequence. Various benzo-fused N-heterocyclic frameworks were achievable under transition metal-free conditions with a broad substrate scope.

  DOI：

  10.1021/jacs.8b01005
• 作为产物：
  描述：

  苯胺,N-(1,1-二甲基-2-炔丙基)-4-甲基- 在 Lindlar's catalyst 氢气 作用下， 生成 N-(1',1'-dimethylallyl)-4-methylaniline
  参考文献：
  名称：

  Untersuchungenüberaromatische氨基-克莱森-Umlagerungen †

  摘要：

  芳香族氨基克莱森重排的研究

  DOI：

  10.1002/hlca.19770600329

文献信息

• Photo-Emde Degradation of 1,2,3,4-Tetrahydroquinolinium Salts
  作者：Vassilia Partali、Syn�se Jolidon、Hans-J�rgen Hansen

  DOI：10.1002/hlca.19850680721

  日期：1985.11.13

  the counterion (I−, BF), a reductive cleavage of the N(1)–C(8a) bond (photo-Emde degradation). The corresponding N,N-dimethyl-3-phenylpropylamines are formed in high yields and without contamination by Hofmann degradation products of the tetrahydroquinolinium salts. Me groups at C(2) as well as substituents at C(6) (CH3, Cl, CH3O) favour the photo-Emde degradation. The aromatic Cl-substituent is reductively

  结果表明，1,1-二甲基-1,2,3,4- tetrahydroquinolinium离子经历，直接照射下通过在CH石英3 OH和独立的平衡离子的性质（I -，BF），的还原裂解N（1）–C（8a）键（光Emde降解）。以高收率形成相应的N，N-二甲基-3-苯基丙胺，而没有被四氢喹啉鎓盐的霍夫曼降解产物污染。C（2）处的Me基团以及C（6）处的取代基（CH 3，Cl，CH 3 O）有利于光Emde降解。在光反应过程中，芳族Cl-取代基被还原分离。
• Investigation of Steric and Electronic Features of 3-Iminophosphine-Based Palladium Catalysts for Intermolecular Hydroamination
  作者：Nicholas C. Zingales、Andrew R. Shaffer、Joseph A. R. Schmidt

  DOI：10.1021/om301102w

  日期：2013.1.28

  A series of (3-iminophosphine)allylpalladium triflate complexes with systematic variation of both steric and electronic features was isolated and characterized. The ability of the complexes in this series to catalyze the regioselective hydroamination of 3-methyl-1,2-butadiene with aryl amines to form solely the kinetic product was probed by observing conversion to products via NMR spectroscopy. The previously unstudied 3-iminophosphine ligand composed of a di-tert-butyl phosphine, cyclobutene backbone, and tert-butyl imine provided the most active palladium hydroamination catalyst for this transformation known to date.
• Regioselective Iron-Catalyzed Allylic Amination
  作者：Bernd Plietker

  DOI：10.1002/anie.200602261

  日期：2006.9.11
• PARTALI, V.;JOLIDON, S.;HANSEN, H. -J., HELV. CHIM. ACTA, 1985, 68, N 7, 1952-1960
  作者：PARTALI, V.、JOLIDON, S.、HANSEN, H. -J.

  DOI：——

  日期：——
• Domino Aryne Annulation via a Nucleophilic–Ene Process
  作者：Hai Xu、Jia He、Jiarong Shi、Liang Tan、Dachuan Qiu、Xiaohua Luo、Yang Li

  DOI：10.1021/jacs.8b01005

  日期：2018.3.14

  1,2-Benzdiyne equivalents possess the unique property that they can react with two arynophiles through iteratively generated 1,2- and 2,3-aryne intermediates. Upon rational modification on the second leaving group of these aryne precursors, a domino aryne annulation approach was developed through a nucleophilic-ene reaction sequence. Various benzo-fused N-heterocyclic frameworks were achievable under transition metal-free conditions with a broad substrate scope.