N-benzyl-1-(biphenyl-4-yl)-N-methylmethanamine | 262371-18-6

• 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-benzyl-1-(biphenyl-4-yl)-N-methylmethanamine
• 英文别名: N-methyl-1-phenyl-N-[(4-phenylphenyl)methyl]methanamine
• CAS: 262371-18-6
• 化学式: C₂₁H₂₁N
• 分子量: 287.404
• InChiKey: CTLHBHNVSAOVQQ-UHFFFAOYSA-N

物化性质

• 沸点：
  405.9±24.0 °C(Predicted)
• 密度：
  1.056±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  溴化氰 、 N-benzyl-1-(biphenyl-4-yl)-N-methylmethanamine 生成 N-苄基-N-甲基氰胺 、 4-溴甲基联苯
  参考文献：
  名称：

  v.Braun; Engel, Justus Liebigs Annalen der Chemie, 1924, vol. 436, p. 315

  摘要：

  DOI：
• 作为产物：
  描述：

  联苯-4-甲醇 在 乙醇 、 氢溴酸 、 sodium carbonate 、 溶剂黄146 作用下， 生成 N-benzyl-1-(biphenyl-4-yl)-N-methylmethanamine
  参考文献：
  名称：

  关于对苯苄基胺衍生物的催化氢解。2.氢解通讯

  摘要：

  通过混合叔胺的氢解，发现了以下一系列增加的类似苄基的氢解裂解的过程：苄基<对-苯基苄基<苯甲基，9-芴基，薄荷基（α和β）。

  DOI：

  10.1002/hlca.19520350437

文献信息

• Thiourea‐Catalyzed C−F Bond Activation: Amination of Benzylic Fluorides
  作者：Camille Houle、Paul R. Savoie、Clotilde Davies、Damien Jardel、Pier Alexandre Champagne、Brigitte Bibal、Jean‐François Paquin

  DOI：10.1002/chem.202001905

  日期：2020.8.17

  thiourea catalyst and Ti(OiPr)4 as a fluoride scavenger allows the amination of benzylic fluorides to proceed in moderate to excellent yields. Preliminary results with S‐ and O‐based nucleophiles are also presented. DFT calculations reveal the importance of hydrogen bonds between the catalyst and the fluorine atom of the substrate to lower the activation energy during the transition state.

  我们描述了第一个硫脲催化的CF键活化。使用硫脲催化剂和Ti（O i Pr）4作为氟化物清除剂可使苄基氟化物的胺化反应以中等至极好的收率进行。还介绍了基于S和O的亲核试剂的初步结果。DFT计算揭示了催化剂和底物氟原子之间氢键对于降低过渡态活化能的重要性。
• Enabling Nucleophilic Substitution Reactions of Activated Alkyl Fluorides through Hydrogen Bonding
  作者：Pier Alexandre Champagne、Julien Pomarole、Marie-Ève Thérien、Yasmine Benhassine、Samuel Beaulieu、Claude Y. Legault、Jean-François Paquin

  DOI：10.1021/ol400765a

  日期：2013.5.3

  It was discovered that the presence of water as a cosolvent enables the reaction of activated alkyl fluorides for bimolecular nucleophilic substitution reactions. DFT calculations show that activation proceeds through stabilization of the transition structure by a stronger F···H2O interaction and diminishing C–F bond elongation, and not simple transition state electrostatic stabilization. Overall,

  已经发现水作为助溶剂的存在使得活化的烷基氟化物能够进行双分子亲核取代反应。DFT计算表明，活化是通过更强的F···H 2 O相互作用稳定过渡结构并减少C-F键伸长而进行的，而不是简单的过渡态静电稳定。总体而言，研究结果提出了通过H键激活CF键的独特策略。
• Triol-promoted activation of C–F bonds: Amination of benzylic fluorides under highly concentrated conditions mediated by 1,1,1-tris(hydroxymethyl)propane
  作者：Pier Alexandre Champagne、Alexandre Saint-Martin、Mélina Drouin、Jean-François Paquin

  DOI：10.3762/bjoc.9.283

  日期：——

  Activation of the C-F bond of benzylic fluorides was achieved using 1,1,1-tris(hydroxymethyl)propane (2) as a hydrogen bond-donating agent. Investigations demonstrated that hydrogen bond-donating solvents are promoting the activation and hydrogen bond-accepting ones are hindering it. However, the reaction is best run under highly concentrated conditions, where solvents cannot interfere with the interaction

  使用 1,1,1-三（羟甲基）丙烷 (2) 作为氢键供体剂来激活苄基氟的 CF 键。研究表明，提供氢键的溶剂促进了活化，而接受氢键的溶剂则阻碍了活化。然而，反应最好在高浓度条件下进行，在这种条件下，溶剂不会干扰有机氟化合物和三醇之间的相互作用。各种苄基氟化物与仲胺或苯胺反应以良好的产率形成苄基胺。
• Dehydroxylation of alcohols for nucleophilic substitution
  作者：Jia Chen、Jin-Hong Lin、Ji-Chang Xiao

  DOI：10.1039/c8cc03856b

  日期：——

  The Ph3P/ICH2CH2I system-promoted dehydroxylative substitution of alcohols was achieved to construct C–O, C–N, C–S and C–X (X = Cl, Br, and I) bonds. Compared with the previous approaches such as the Appel reaction and Mitsunobu reaction, this protocol offers some practical advantages such as safe operation and a convenient amination process.

  通过Ph 3 P / ICH 2 CH 2 I系统促进的醇的脱羟基取代反应，可构建C–O，C–N，CS–S和C–X（X = Cl，Br和I）键。与之前的方法（如Appel反应和Mitsunobu反应）相比，该方案具有一些实用的优点，例如操作安全和便捷的胺化过程。
• Anomalous lumbrical muscles arising from the deep surface of flexor digitorum superficialis muscles in man
  作者：Masahiro Koizumi、Katsushi Kawai、Satoru Honma、Kodo Kodama

  DOI：10.1016/s0940-9602(02)80062-0

  日期：2002.7

  During anatomy practice in 1999 at Kumamoto University School of Medicine, the anomalous lumbrical muscles originating in the forearm were observed in both arms of a cadaver. These muscles, originating from the intermediate tendon of the deep layer of the flexor digitorum superficialis for the index finger (FDS-II), passed through the carpal tunnel to join the insertion of the first lumbrical muscle, and formed a muscle belly near the origin in the left and at the insertion in the right. The left anomalous muscle was innervated by a branch of the median nerve just proximal to the carpal tunnel. The right one received a twig from the nerve to the first lumbrical muscle. Tracing the nerve fibers by peeling off the epi- and perineurium clarified that the nerve fibers supplying the left anomalous muscle formed a common bundle with the fibers to the first lumbrical muscle. Therefore, these anomalous muscles are considered to be the accessory lumbrical muscles arising from the forearm. The three accessory lumbricalis, including one case reported by Yamada (1986), received branches which had slightly different origins from proximally (nerve to the distal belly of FDS-II) to distally (nerve to the first lumbricalis). Accordingly the position of the muscle belly shifted distally. The occurrence of these unusual accessory lumbrical muscles indicates that the distal belly of FDS-II and the first lumbricalis are derived from a common muscle origin and presents an important clue to the phylogenetic origin of the flexor digitorum superficialis.