bis(1-phenylethyl)amine

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: bis(1-phenylethyl)amine
• 英文别名: (1S)-1-phenyl-N-(1-phenylethyl)ethanamine
• 化学式: C₁₆H₁₉N
• 分子量: 225.334
• InChiKey: NXLACVVNHYIYJN-LSLKUGRBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (S)-(-)-N-(methyldibenzylidene)-α-methylbenzylamine 在 三氢化钐 、 碘 作用下， 以 甲醇 为溶剂， 生成 bis(1-phenylethyl)amine
  参考文献：
  名称：

  Banik; Ghatak; Samajdar, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2001, vol. 40, # 11, p. 1134 - 1139

  摘要：

  DOI：

文献信息

• Microwave-Assisted Catalytic Intermolecular Hydroamination of Alkynes
  作者：Igor Bytschkov、Sven Doye

  DOI：10.1002/1099-0690(200112)2001:23<4411::aid-ejoc4411>3.0.co;2-n

  日期：2001.12

  microwave technology, it is possible to achieve turnover frequencies TOF > 10 h−1. Furthermore, when Cp2TiMe2 is used as the catalyst, hydroamination products of terminal alkynes can be isolated in reasonable yields for the first time. The addition of amines to terminal alkynes gives access to both the Markovnikov and the anti-Markovnikov products. Observed regioselectivities are different for terminal

  用频率为 2.45 GHz 和功率输出为 180-300 W 的微波辐照在甲苯中含有炔烃、胺和催化量的 Cp2TiMe2 的反应混合物，导致快速反应，得到相应的加氢胺化产物。最初形成的亚胺可以通过使用 H2/Pd、LiAlH4 或 NaCNBH3/p-TsOH 轻松还原为仲胺。微波辅助加氢胺化反应在 105 °C 油浴中常规反应所需时间的十分之一（或更少）内完成。通过使用微波技术，可以实现周转频率 TOF > 10 h-1。此外，当使用 Cp2TiMe2 作为催化剂时，可以首次以合理的产率分离末端炔烃的加氢胺化产物。向末端炔烃添加胺可以得到马尔科夫尼科夫和反马尔科夫尼科夫产物。观察到的区域选择性对于末端芳基和烷基炔是不同的。
• Chiral Frustrated Lewis Pair@Metal‐Organic Framework as a New Platform for Heterogeneous Asymmetric Hydrogenation
  作者：Yin Zhang、Songbo Chen、Abdullah M. Al‐Enizi、Ayman Nafady、Zhiyong Tang、Shengqian Ma

  DOI：10.1002/anie.202213399

  日期：2023.1.9

  A highly active heterogeneous chiral frustrated Lewis pair system has been achieved for the first time via incorporating rationally designed bifunctional chiral FLP molecules into a MOF under the guidance of computational studies; the afforded CFLP@MOF demonstrated superb catalysis performances in heterogeneous asymmetric hydrogenation with excellent recyclability/regenerability.

  在计算研究的指导下，通过将合理设计的双功能手性 FLP 分子结合到 MOF 中，首次实现了高活性异构手性受挫路易斯对系统；所提供的 CFLP@MOF 在多相不对称氢化中表现出卓越的催化性能，具有出色的可回收性/再生性。
• Ytterbium Acetate Promoted Asymmetric Reductive Amination:  Significantly Enhanced Stereoselectivity
  作者：Thomas C. Nugent、Mohamed El-Shazly、Vijay N. Wakchaure

  DOI：10.1021/jo7021235

  日期：2008.2.1

  Reductive amination of prochiral unhindered 2-alkanones 1 with (R)- or (S)-alpha-MBA in the presence of Yb(OAc)(3) (50-110 mol %), Raney-Ni, and hydrogen (120 psi) results in increased diastereoselectivity for the amine products 2 (80-89% de) with good yield (80-87%). The increased de is based on comparison with the best previously reported de's when using (R)- or (S)-alpha-MBA, regardless of the strategy employed [stepwise (isolation of ketimines) or one-pot (reductive amination)], reducing agent examined, or achiral Lewis acid or Bronsted acid examined. An in situ cis- to trans-ketimine isomerization mechanism, promoted by Yb(OAC)(3), has been proposed to account for the observed increase in diastereoselectivity and suggests a new entry into the control of ketimine geometry.
• A practical, solvent free, one-pot synthesis of C 2 -symmetrical secondary amines
  作者：Alexandre Alexakis、Ségolène Gille、Fabrice Prian、Stéphane Rosset、Klaus Ditrich

  DOI：10.1016/j.tetlet.2003.12.037

  日期：2004.2

  A novel one-pot reductive amination of ketones using the combination Ti((OPr)-Pr-i)(4)/H-2/Pd-C is reported. This practical procedure does not require any solvent, and affords C-2-symmetrical secondary amines in high yields and excellent diastereoselectivities. (C) 2003 Elsevier Ltd. All rights reserved.
• Banik; Ghatak; Samajdar, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2001, vol. 40, # 11, p. 1134 - 1139
  作者：Banik、Ghatak、Samajdar、Basu、Hackfeld、Banik、Zegrocka、Becker

  DOI：——

  日期：——