biphenyl-4-ylmethyl-butyl-amine

• 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: biphenyl-4-ylmethyl-butyl-amine
• 英文别名: N-[(4-phenylphenyl)methyl]butan-1-amine
• 化学式: C₁₇H₂₁N
• mdl: MFCD07407293
• 分子量: 239.36
• InChiKey: OLVPJPWEIMFIGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.294
• 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：

  N-butyl-1-(4-phenylphenyl)methanimine 在 sodium tetrahydroborate 作用下， 生成 biphenyl-4-ylmethyl-butyl-amine
  参考文献：
  名称：

  Synthesis and bioevaluation of N-(arylalkyl)-homospermidine conjugates

  摘要：

  N'-(Arylalkyl)homospermidines (Ic-1f) and terminally piperazine-substituted homospermidine conjugates (2a-2e) were synthesized and evaluated for cytotoxicity in mouse leukemia L 1210, alpha-difluorometliylornithine (DFMO)-treated L 12 10, melanoma B 16, spermidine (SPD)-treated B 16, and HeLa cell lines. Results demonstrated that homospermidine was a more effective vector than piperazine-substituted homospermidine in ferrying diverse arenes into cells via the polyamine transporter. The leading compound, 9-anthracenemethyl-homospermidine (1a), was shown to induce apoptosis in B16 cells and IL-3 dependent FL5.12A proB cells. The novel conjugate 4-biphenylmethyl-homospermidine (1e) could also induce apoptosis. However, it exhibited different effect on the cell cycle of B16 cells compared to la. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.06.009

文献信息

• 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。
• Palladium- and Nickel-Catalyzed Cross-Couplings of Unsaturated Halides Bearing Relatively Acidic Protons with Organozinc Reagents
  作者：Georg Manolikakes、Carmen Muñoz Hernandez、Matthias A. Schade、Albrecht Metzger、Paul Knochel

  DOI：10.1021/jo8015852

  日期：2008.11.7

  aryl, heteroaryl, alkyl, and benzylic zinc reagents were coupled with unsaturated aryl halides bearing an acidic NH or OH proton, using Pd(OAc)2 (1 mol %) and S-Phos (2 mol %) as catalyst without the need of protecting groups. A similar nickel-catalyzed reaction is described. The relative kinetic basicity of organozinc compounds as well as their stability toward acidic protons is also described.

  多种多官能芳基，杂芳基，烷基和苄基锌试剂与带有酸性NH或OH质子的不饱和芳基卤化物偶合，使用Pd（OAc）2（1 mol％）和S-Phos（2 mol％）作为不需要保护基的催化剂。描述了类似的镍催化反应。还描述了有机锌化合物的相对动力学碱性及其对酸性质子的稳定性。
• [EN] INHIBITING OTUB1<br/>[FR] INHIBITION DE L'OTUB1
  申请人：INTEGRAL EARLY DISCOVERY INC

  公开号：WO2020223551A1

  公开（公告）日：2020-11-05

  The present disclosure is directed to compounds of formulas (I) - (VII), which are useful as modulators of OTUB1. The compounds are further useful in the inhibition of OTUB1 and the treatment of diseases or disorders associated with the inhibition of OTUB1. For instance, the disclosure is concerned with compounds and compositions for inhibition of OTUB1, methods of treating diseases associated with the inhibition of OTUB1 (e.g., inflammatory diseases like irritable bowel disease and Lupus), and methods of synthesis of these compounds.

  本公开涉及的是公式(I)-(VII)的化合物，它们可用作OTUB1的调节剂。这些化合物还可用于抑制OTUB1和治疗与抑制OTUB1相关的疾病或疾病。例如，本公开涉及用于抑制OTUB1的化合物和组合物，治疗与抑制OTUB1相关的疾病的方法（例如，炎症性疾病，如肠易激综合征和红斑狼疮），以及这些化合物的合成方法。
• Synthesis of Amines by the Intermolecular Schmidt Reaction of Aliphatic Azides with Carbocations
  作者：William H. Pearson、Wen-kui Fang

  DOI：10.1021/jo00121a001

  日期：1995.8
• Synthesis and bioevaluation of N-(arylalkyl)-homospermidine conjugates
  作者：Songqiang Xie、Pengfei Cheng、Guangchao Liu、Yuangfang Ma、Jin Zhao、Mounir Chehtane、Annette R. Khaled、Otto Phanstiel、Chaojie Wang

  DOI：10.1016/j.bmcl.2007.06.009

  日期：2007.8

  N'-(Arylalkyl)homospermidines (Ic-1f) and terminally piperazine-substituted homospermidine conjugates (2a-2e) were synthesized and evaluated for cytotoxicity in mouse leukemia L 1210, alpha-difluorometliylornithine (DFMO)-treated L 12 10, melanoma B 16, spermidine (SPD)-treated B 16, and HeLa cell lines. Results demonstrated that homospermidine was a more effective vector than piperazine-substituted homospermidine in ferrying diverse arenes into cells via the polyamine transporter. The leading compound, 9-anthracenemethyl-homospermidine (1a), was shown to induce apoptosis in B16 cells and IL-3 dependent FL5.12A proB cells. The novel conjugate 4-biphenylmethyl-homospermidine (1e) could also induce apoptosis. However, it exhibited different effect on the cell cycle of B16 cells compared to la. (c) 2007 Elsevier Ltd. All rights reserved.