1,3,5-tris(4-methylphenyl)-2,4-diazapenta-1,4-diene

• 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: 1,3,5-tris(4-methylphenyl)-2,4-diazapenta-1,4-diene
• 英文别名: N,N'-bis<4-methylbenzylidene>-4-methylphenylmethanediamine；N,N'-(p-tolylmethylene)bis(1-p-tolylmethanimine)；1-(4-methylphenyl)-N-[(4-methylphenyl)-[(4-methylphenyl)methylideneamino]methyl]methanimine
• 化学式: C₂₄H₂₄N₂
• 分子量: 340.468
• InChiKey: UXGFPCAZAOEVCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  24.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,3,5-tris(4-methylphenyl)-2,4-diazapenta-1,4-diene 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以95%的产率得到bis(4-methylbenzyl)amine
  参考文献：
  名称：

  Highly chemoselective reductive amination-coupling by one-pot reaction of aldehydes, HMDS and NaBH4

  摘要：

  An efficient and highly chemoselective synthesis of symmetrical secondary amines via reductive amination of aldehydes with inexpensive and commercially available HMDS and sodium borohydride in high to quantitative yields is reported. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.09.048
• 作为产物：
  描述：

  4,4'-dimethyl-α,α'-imino-di-benzyl alcohol 生成 1,3,5-tris(4-methylphenyl)-2,4-diazapenta-1,4-diene
  参考文献：
  名称：

  Francis, Chemische Berichte, 1909, vol. 42, p. 2216

  摘要：

  DOI：

文献信息

• Adducts of Triallylborane with Ammonia and Aliphatic Amines as Stoichiometric Allylating Agents for Aminoallylation Reaction of Carbonyl Compounds
  作者：Nikolai Yu. Kuznetsov、Rabdan M. Tikhov、Tatiana V. Strelkova、Yuri N. Bubnov

  DOI：10.1021/acs.orglett.8b01317

  日期：2018.6.15

  Triallylborane–amines adducts are effective stoichiometric allylating agents in the aminoallylation reaction of carbonyl compounds in methanol. Moreover, copper-catalyzed diastereoselective allylation of Ellman’s imine was achieved with triallylborane–methylamine adduct.

  三烯丙基硼烷-胺加合物在甲醇中羰基化合物的氨基烯丙基化反应中是有效的化学计量烯丙基化剂。此外，用三烯丙基硼烷-甲胺加合物实现了铜催化的埃尔曼亚胺的非对映选择性烯丙基化。
• Synthesis of β-Phosphinolactams from Phosphenes and Imines
  作者：Xingyang Fu、Xinyao Li、Jiaxi Xu

  DOI：10.1021/acs.orglett.1c03182

  日期：2021.11.19

  Various cis-β-phosphinolactams are synthesized stereoselectively for the first time from imines and diazo(aryl)methyl(diaryl)phosphine oxides under microwave irradiation. Diazo(aryl)methyl(diaryl)phosphine oxides first undergo the Wolf rearrangement to generate phosphenes. Imines nucleophilically attack the phosphenes followed by an intramolecular nucleophilic addition via less steric transition states

  在微波辐射下，首次从亚胺和重氮（芳基）甲基（二芳基）氧化膦立体选择性地合成了各种顺式-β-膦内酰胺。重氮（芳基）甲基（二芳基）氧化膦首先经历沃尔夫重排以生成膦。亚胺亲核攻击膦，然后通过较少的空间过渡态进行分子内亲核加成，得到最终的顺式-β-膦内酰胺。C-苯乙烯亚胺通常以比C-芳基亚胺更高的产率产生 β-膦内酰胺。通过 DFT 理论计算对立体选择性和提出的机制进行了合理化。
• Annulation of Diaryl(aryl)phosphenes and Cyclic Imines to Access Benzo-δ-phospholactams
  作者：Yun Luo、Jiaxi Xu

  DOI：10.1021/acs.orglett.0c02346

  日期：2020.10.16

  Microwave-assisted annulation of cyclic imine dibenzo[b,f][1,4]oxazepines and diaryl(aryl)phosphenes generated from diazo(aryl)methyl(diaryl)phosphine oxides through the Wolff rearrangement accesses pentacyclic benzo-δ-phospholactams, 4b,16-dihydrodibenzo[b,f]benzo[4,5][1,2]azaphosphinino[1,6-d][1,4]oxazepine 15-oxides, in good yields.

  环亚胺二苯并[ b，f ] [1,4]氮杂ox庚因和重氮芳基甲基（二芳基）膦氧化物通过Wolff重排生成的二芳基（芳基）膦的微波辅助环化反应获得五环苯并-δ-膦内酰胺，4b ，16-二氢二苯并[ b，f ]苯并[4,5] [1,2]氮杂膦基[1,6- d ] [1,4]奥氮平15-氧化物，收率良好。
• Design, Synthesis, and <i>In Vitro</i> and <i>In Vivo</i> Biological Evaluation of Limonin Derivatives for Anti-Inflammation Therapy
  作者：Ming Bian、Guohua Gong、Pang Lei、Huanhuan Du、Chunmei Bai、Chengxi Wei、Zheshan Quan、Qianqian Ma

  DOI：10.1021/acs.jafc.1c04989

  日期：2021.11.17

  In this study, limonin derivatives were used to design new anti-inflammatory compounds with high pharmacological activity and low toxicity. A total of 23 new limonin derivatives were discovered, synthesized, and screened for their anti-inflammatory activity against lipopolysaccharide (LPS)-treated RAW 264.7 cells. Of them, compound f4 was found to be the most active, with a higher efficiency compared

  在这项研究中，柠檬苦素衍生物用于设计具有高药理活性和低毒性的新型抗炎化合物。总共发现、合成了 23 种新的柠檬苦素衍生物，并筛选了它们对脂多糖 (LPS) 处理的 RAW 264.7 细胞的抗炎活性。其中，发现化合物f4活性最高，与柠檬苦素和塞来昔布相比具有更高的效率。随后，我们研究了f4活性的潜在机制，发现它通过阻断 LPS 处理的 RAW 264.7 细胞和小鼠中的 NF-κB/MAPK 信号通路来抑制促炎细胞因子。总之，f4可能是一种很有前途的抗炎先导化合物。
• Novel Method for the Synthesis of α-Amino-α′-hydroxyalkylphosphinic Acids and Bis(α-aminoalkyl)phosphinic Acids: Nuclephilic Addition of α-Hydroxy-H-phosphinic Acids to Diimines
  作者：Babak Kaboudin、Hamideh Haghighat、Saied Alaie、Tsutomu Yokomatsu

  DOI：10.1055/s-0032-1316706

  日期：2012.8

  here a novel and simple method for the synthesis of α-amino-α′-hydroxyalkylphosphinic acids in good yields in two simple steps without any protection–deprotection steps. We have developed an efficient method for the synthesis of α-amino-α′-hydroxyalkylphosphinic acids via the reaction of easily available α-hydroxyalkylphosphinic acids with diimines. Treatment of α-­hydroxyalkylphosphinic acids with diimines

  我们在此报告了一种新颖且简单的方法，可通过两个简单的步骤以良好的收率合成 α-氨基-α'-羟烷基次膦酸，无需任何保护-脱保护步骤。我们开发了一种通过容易获得的 α-羟烷基次膦酸与二亚胺反应合成 α-氨基-α'-羟烷基次膦酸的有效方法。在三甲基甲硅烷基氯 (TMSCl) 存在下用二亚胺处理 α-羟烷基次膦酸以良好的收率得到 α-氨基-α'-羟烷基次膦酸。该反应得到α-氨基-α'-羟基烷基次膦酸的两种非对映异构形式的混合物。在有机溶剂中溶解度的差异使我们能够轻松地分离非对映异构体。