1-(4-(benzyloxy)phenyl)-4-(4-methoxyphenyl)-N-methylbut-3-yn-2-amine | 1262680-30-7

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: 1-(4-(benzyloxy)phenyl)-4-(4-methoxyphenyl)-N-methylbut-3-yn-2-amine
• 英文别名: 4-(4-methoxyphenyl)-N-methyl-1-(4-phenylmethoxyphenyl)but-3-yn-2-amine
• CAS: 1262680-30-7
• 化学式: C₂₅H₂₅NO₂
• 分子量: 371.479
• InChiKey: GYZDPGNXQFBJLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-(benzyloxy)phenyl)-4-(4-methoxyphenyl)-N-methylbut-3-yn-2-amine 在 三甲基氯硅烷 、 silver nitrate 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 2.17h， 生成 (2Z,5Z)-benzyl 4-(4-(benzyloxy)benzyl)-2-((2-fluorobenzoyl)imino)-5-(4-methoxybenzylidene)-3-methylimidazolidine-1-carboxylate
  参考文献：
  名称：

  [EN] COMPOSITIONS AND METHODS COMPRISING 2-(ACYLAMINO)IMIDAZOLES
  [FR] COMPOSITIONS ET PROCÉDÉS COMPRENANT DES 2- (ACYLAMINO) IMIDAZOLES

  摘要：

  公开号：

  WO2015143240A3
• 作为产物：
  描述：

  2-(4-(苄氧基)苯基)乙醛 在 四(三苯基膦)钯 、 硫代水杨酸 、 copper(I) bromide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 24.0h， 生成 1-(4-(benzyloxy)phenyl)-4-(4-methoxyphenyl)-N-methylbut-3-yn-2-amine
  参考文献：
  名称：

  Synthesis of Naamidine A and Selective Access to N²-Acyl-2-aminoimidazole Analogues

  摘要：

  A short and scalable synthesis of naamidine A, a marine alkaloid with a selective ability to inhibit epidermal growth factor receptor (EGFR)-dependent cellular proliferation, has been achieved. A key achievement in this synthesis was the development of a regioselective hydroamination of a monoprotected propargylguanidine to deliver N-3-protected cyclic ene-guanidines. This permits the extension of this methodology to prepare N-2-acyl analogues in a fashion that obviates the troublesome acylation of the free 2-aminoimidazoles, which typically yields mixtures of N-2- and N-2,N-2-diacylated products.

  DOI：

  10.1021/acs.joc.5b01703

文献信息

• Concise and Diversity-Oriented Route toward Polysubstituted 2-Aminoimidazole Alkaloids and Their Analogues
  作者：Denis S. Ermolat'ev、Jitender B. Bariwal、Hans P. L. Steenackers、Sigrid C. J. De Keersmaecker、Erik V. Van der Eycken

  DOI：10.1002/anie.201004256

  日期：2010.12.3

  Alkaloids of the naamine family were synthesized from diverse propargylamines in just two steps (see scheme: R1=Me, R2=substituted benzyl, R3=Ar). Thus, the addition to a propargylamine of a carbodiimide generated in situ, silver(I)‐catalyzed intramolecular hydroamidation, and subsquent deprotection provide access to the heterocyclic core of numerous natural products and biologically active compounds

  纳胺家族的生物碱仅需两个步骤就可以由多种炔丙基胺合成（参见方案：R 1 = Me，R 2 =取代的苄基，R 3 = Ar）。因此，除了在炔丙基胺中原位生成的碳二亚胺之外，银（I）催化的分子内加氢酰胺化作用以及随后的脱保护作用也使人们可以接近许多天然产物和生物活性化合物的杂环核。Boc =叔丁氧羰基，Cbz =碳苄氧基。
• Compositions and methods comprising 2-(acylamino)imidazoles
  申请人：Curza Global, LLC

  公开号：US10493061B2

  公开（公告）日：2019-12-03

  The present invention presents 2-(acylamino)imidazoles with therapeutic activity, including selective activity against cancer cells, and compositions comprising them. Methods of using and preparing the 2-(acylamino)imidazoles are also presented.

  本发明提出了具有治疗活性（包括对癌细胞的选择性活性）的 2-(酰氨基)咪唑以及包含它们的组合物。本发明还提出了使用和制备 2-（酰氨基）咪唑的方法。
• COMPOSITIONS AND METHODS COMPRISING 2-(ACYLAMINO)IMIDAZOLES
  申请人：Curza Global LLC

  公开号：EP3119394B1

  公开（公告）日：2021-05-12
• [EN] COMPOSITIONS AND METHODS COMPRISING 2-(ACYLAMINO)IMIDAZOLES<br/>[FR] COMPOSITIONS ET PROCÉDÉS COMPRENANT DES 2- (ACYLAMINO) IMIDAZOLES
  申请人：CURZA GLOBAL LLC

  公开号：WO2015143240A3

  公开（公告）日：2015-11-12
• Synthesis of Naamidine A and Selective Access to N²-Acyl-2-aminoimidazole Analogues
  作者：Joseph B. Gibbons、Justin M. Salvant、Rachel M. Vaden、Ki-Hyeok Kwon、Bryan E. Welm、Ryan E. Looper

  DOI：10.1021/acs.joc.5b01703

  日期：2015.10.16

  A short and scalable synthesis of naamidine A, a marine alkaloid with a selective ability to inhibit epidermal growth factor receptor (EGFR)-dependent cellular proliferation, has been achieved. A key achievement in this synthesis was the development of a regioselective hydroamination of a monoprotected propargylguanidine to deliver N-3-protected cyclic ene-guanidines. This permits the extension of this methodology to prepare N-2-acyl analogues in a fashion that obviates the troublesome acylation of the free 2-aminoimidazoles, which typically yields mixtures of N-2- and N-2,N-2-diacylated products.