(S)-4-methoxy-N-(1-p-tolylpropyl)aniline | 1073339-58-8

• 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: (S)-4-methoxy-N-(1-p-tolylpropyl)aniline
• 英文别名: 4-methoxy-N-[(1S)-1-(4-methylphenyl)propyl]aniline
• CAS: 1073339-58-8
• 化学式: C₁₇H₂₁NO
• 分子量: 255.36
• InChiKey: CTCCNCRZTFYWKQ-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  在 (11bS)-4-羟基-2,6-二[2,4,6-三(异丙基)苯基]-二萘并[2,1-d:1',2'-f][1,3,2]二氧杂磷杂卓4-氧化物 、 C₈₅H₁₀₂IrN₂O₆PS 、 氢气 作用下， 以 甲苯 为溶剂， 20.0 ℃ 、2.0 MPa 条件下， 反应 15.0h， 以93%的产率得到(S)-4-methoxy-N-(1-p-tolylpropyl)aniline
  参考文献：
  名称：

  Chiral Counteranion-Aided Asymmetric Hydrogenation of Acyclic Imines

  摘要：

  When combined with a chiral phosphate counteranion, a chiral diamine-ligated Ir(III) catalyst displayed excellent enantioselectivities in the asymmetric hydrogenation of a wide range of acyclic imines, affording chiral amines in up to 99% ee.

  DOI：

  10.1021/ja807188s

文献信息

• Catalytic Enantioselective Amination of Alcohols by the Use of Borrowing Hydrogen Methodology: Cooperative Catalysis by Iridium and a Chiral Phosphoric Acid
  作者：Yao Zhang、Ching-Si Lim、Derek Sui Boon Sim、Hui-Jie Pan、Yu Zhao

  DOI：10.1002/anie.201307789

  日期：2014.1.27

  synthesis of chiral amines, with reductants ranging from Hantzsch esters, silanes, and formic acid to H2 gas. Alternatively, the amination of alcohols by the use of borrowing hydrogen methodology has proven a highly atom economical and green method for the production of amines without an external reductant, as the alcohol substrate serves as the H2 donor. A catalytic enantioselective variant of this

  酮亚胺的催化不对称还原已经广泛地用于手性胺的合成，还原剂的范围从汉茨（Hantzsch）酯，硅烷和甲酸到H 2气体。或者，由于使用醇底物作为H 2，通过借用氢方法进行的醇胺化已被证明是一种高度原子经济且绿色的方法，无需外部还原剂即可生产胺。捐赠者。然而，用于合成手性胺的该方法的催化对映选择性变体是未知的。我们已经研究了由不对称氢化反应已知的手性配体所支持的各种过渡金属配合物，以及手性布朗斯台德酸，它们被证明对于亚胺中间体的形成和转移加氢步骤至关重要。我们的研究导致了醇的不对称胺化，从而提供了具有良好或优异的对映选择性的多种手性胺。
• Chiral Phosphoric‐Acid‐Catalyzed Transfer Hydrogenation of Ethyl Ketimine Derivatives by Using Benzothiazoline
  作者：Kodai Saito、Kosaku Horiguchi、Yukihiro Shibata、Masahiro Yamanaka、Takahiko Akiyama

  DOI：10.1002/chem.201402763

  日期：2014.6.16

  Chiral phosphoric acid catalyzed transfer hydrogenation of ketimines derived from propiophenone derivatives and reductive amination of alkyl ethyl ketone derivatives were extensively examined in the presence of two representative hydrogen donors. The excellent enantioselective transfer hydrogenation was achieved by use of benzothiazoline as a hydrogen donor. The theoretical studies elucidated that

  在两个代表性氢供体的存在下，广泛研究了手性磷​​酸催化衍生自苯乙酮衍生物的酮亚胺的转移氢化和烷基乙基酮衍生物的还原胺化。通过使用苯并噻唑啉作为氢供体实现了优异的对映选择性转移氢化。理论研究表明，苯并噻唑啉的不对称结构在高对映选择性氢化中起重要作用。
• Oxidative Kinetic Resolution of Acyclic Amines Based on Equilibrium Control
  作者：Kodai Saito、Hiromitsu Miyashita、Yui Ito、Masahiro Yamanaka、Takahiko Akiyama

  DOI：10.1021/acs.orglett.0c00887

  日期：2020.4.17

  An oxidative kinetic resolution of racemic acyclic amines was developed using an imine derivative as the resolving reagent and chiral phosphoric acid as the catalyst to give enantiomers in good yields with high to excellent enantioselectivities. The key to success of the title reaction was the equilibrium control by adjusting the ratio of the resolving reagent, and unique enantiodivergence was observed

  使用亚胺衍生物作为拆分试剂，手性磷酸作为催化剂，开发了外消旋无环胺的氧化动力学拆分方法，从而以高收率和优异的对映选择性获得了对映异构体。标题反应成功的关键是通过调节拆分试剂的比例进行平衡控制，并根据平衡位移观察到独特的对映体。
• Asymmetric Transfer Hydrogenation of Imines using Alcohol: Efficiency and Selectivity are Influenced by the Hydrogen Donor
  作者：Hui-Jie Pan、Yao Zhang、Chunhui Shan、Zhaoyuan Yu、Yu Lan、Yu Zhao

  DOI：10.1002/anie.201604025

  日期：2016.8.8

  The influence of the alcohol, as the hydrogen donor, on the efficiency and selectivity of the asymmetric transfer hydrogenation (ATH) of imines is reported for the first time. This discovery not only leads to a highly enantioselective access to N‐aryl and N‐alkyl amines, but also provides new insight into the mechanism of the ATH of imines. Both experimental and computational studies provide support

  首次报道了作为氢供体的醇对亚胺的不对称转移氢化（ATH）的效率和选择性的影响。这一发现不仅导致对N-芳基和N-烷基胺的高度对映选择性，而且为亚胺ATH的机理提供了新的见解。实验研究和计算研究均为涉及铱醇盐作为还原物种的反应途径提供了支持。