2,3-diphenylpropanenitrile

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2,3-diphenylpropanenitrile
• 英文别名: (2R)-2,3-diphenylpropanenitrile
• 化学式: C₁₅H₁₃N
• 分子量: 207.275
• InChiKey: DRONDEZXOJEUGU-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  α-苯基肉桂腈 在 C₁₇H₃₃ClIrNP₂ 、 氢气 、 potassium hydroxide 作用下， 以 甲醇 为溶剂， 25.0 ℃ 、5.07 MPa 条件下， 反应 24.0h， 生成 2,3-diphenylpropanenitrile 、 2,3-diphenylpropanenitrile
  参考文献：
  名称：

  P-Stereogenic pincer iridium complexes: Synthesis, structural characterization and application in asymmetric hydrogenation

  摘要：

  P-Stereogenic PNP type pincer iridium complexes (PNPIrH2Cl)-Ir-tBuMe (3) and (PNPIrH3)-Ir-tBuMe (4) were synthesized in reasonable yields and characterized by H-1 NMR, C-13 NMR, P-31 NMR, HRMS and/or single crystal X-ray diffraction. The ORTEP diagram shows that the coordination geometry around the iridium center of complex 3 is approximately octahedral. The chlorinated iridium complex (3) and/or the trihydride iridium complex (4) were used as catalysts in the asymmetric hydrogenation of ketones, olefins and quinoline to provide the desired products with up to 17% enantioselectivity. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2015.05.002

文献信息

• Dual electrocatalysis enables enantioselective hydrocyanation of conjugated alkenes
  作者：Lu Song、Niankai Fu、Brian G. Ernst、Wai Hang Lee、Michael O. Frederick、Robert A. DiStasio、Song Lin

  DOI：10.1038/s41557-020-0469-5

  日期：2020.8

  Chiral nitriles and their derivatives are prevalent in pharmaceuticals and bioactive compounds. Enantioselective alkene hydrocyanation represents a convenient and efficient approach for synthesizing these molecules. However, a generally applicable method featuring a broad substrate scope and high functional group tolerance remains elusive. Here, we address this long-standing synthetic problem using

  手性腈及其衍生物普遍存在于药物和生物活性化合物中。对映选择性烯烃氢氰化代表了合成这些分子的方便而有效的方法。然而，具有广泛的底物范围和高的官能团耐受性的普遍适用的方法仍然难以捉摸。在这里，我们使用双重电催化技术解决了这一长期存在的合成问题。使用这种策略，我们利用电化学技术无缝地结合了两个规范的自由基反应（钴介导的氢原子转移和铜促进的自由基氰化），无需化学计量的氧化剂即可实现高度对映选择性的氢氰化。我们还利用电化学精确控制电位的独特功能来优化具有挑战性的底物的化学选择性。计算分析揭示了对映体诱导的起源，为此，手性催化剂结合了吸引性和排斥性非共价相互作用的组合，以指导对映体确定C-CN键的形成。这项工作展示了电化学在进入新的化学领域并为合成化学中的相关挑战提供解决方案方面的力量。
• Enantioselective Arylcyanation of Styrenes <i>via</i> <scp>Copper‐Catalyzed</scp> Radical Relay ^†
  作者：Weiwen Zhuang、Pinhong Chen、Guosheng Liu

  DOI：10.1002/cjoc.202000494

  日期：2021.1

  The first copper‐catalyzed enantioselective arylcyanation of styrenes has been developed using readily available anilines as aryl radical precursors under mild conditions, which enables easy access to chiral 2,3‐diaryl propionitriles with moderate to good enantioselectivities. This operationally straightforward reaction exhibits broad substrate scope and functional group tolerance. Notably, this method

  在温和的条件下，使用容易获得的苯胺作为芳基自由基前体开发了苯乙烯的第一个铜催化的对映选择性芳基氰化反应，这使得容易获得具有中等至良好对映选择性的手性2,3-二芳基丙腈。该操作简单的反应显示出广泛的底物范围和官能团耐受性。值得注意的是，该方法已应用于手性AIEgen以及雌激素受体-β激动剂（R）-二芳基丙腈（DPN）的合成。
• Cu-catalyzed enantioselective decarboxylative cyanation <i>via</i> the synergistic merger of photocatalysis and electrochemistry
  作者：Yin Yuan、Junfeng Yang、Junliang Zhang

  DOI：10.1039/d2sc05428k

  日期：——

  The development of an efficient and straightforward method for decarboxylative coupling using common alkyl carboxylic acid is of great value. However, decarboxylative coupling with nucleophiles always needs stoichiometric chemical oxidants or substrate prefunctionalization. Herein, we report a protocol for Cu-catalyzed enantioselective decarboxylative cyanation via the merger of photocatalysis and

  开发一种使用普通烷基羧酸进行脱羧偶联的有效且简单的方法具有重要价值。然而，与亲核试剂的脱羧偶联总是需要化学计量的化学氧化剂或底物预功能化。在此，我们报告了通过光催化和电化学相结合的铜催化对映选择性脱羧氰化的方案。 CeCl 3和Cu/BOX作为助催化剂促进脱羧和氰化，两种催化剂均通过阳极氧化再生。该方法通过光电催化建立了对映选择性转化的概念验证。 DFT 计算研究提供了对映选择性控制的机制见解。
• P-Stereogenic pincer iridium complexes: Synthesis, structural characterization and application in asymmetric hydrogenation
  作者：Zehua Yang、Xuan Wei、Delong Liu、Yangang Liu、Masashi Sugiya、Tsuneo Imamoto、Wanbin Zhang

  DOI：10.1016/j.jorganchem.2015.05.002

  日期：2015.8

  P-Stereogenic PNP type pincer iridium complexes (PNPIrH2Cl)-Ir-tBuMe (3) and (PNPIrH3)-Ir-tBuMe (4) were synthesized in reasonable yields and characterized by H-1 NMR, C-13 NMR, P-31 NMR, HRMS and/or single crystal X-ray diffraction. The ORTEP diagram shows that the coordination geometry around the iridium center of complex 3 is approximately octahedral. The chlorinated iridium complex (3) and/or the trihydride iridium complex (4) were used as catalysts in the asymmetric hydrogenation of ketones, olefins and quinoline to provide the desired products with up to 17% enantioselectivity. (C) 2015 Elsevier B.V. All rights reserved.