3-(N,N-dimethylamino)-1-(1-methyl-1H-benzimidazol-2-yl)prop-2-en-1-one | 1251916-03-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 3-(N,N-dimethylamino)-1-(1-methyl-1H-benzimidazol-2-yl)prop-2-en-1-one
• 英文别名: 3-(Dimethylamino)-1-(1-methylbenzimidazol-2-yl)prop-2-en-1-one；3-(dimethylamino)-1-(1-methylbenzimidazol-2-yl)prop-2-en-1-one
• CAS: 1251916-03-6
• 化学式: C₁₃H₁₅N₃O
• 分子量: 229.282
• InChiKey: LXRTULKVTBBTGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  38.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(N,N-dimethylamino)-1-(1-methyl-1H-benzimidazol-2-yl)prop-2-en-1-one 在 ammonium hydroxide 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 36.0h， 生成
  参考文献：
  名称：

  Organocatalytic Enantioselective Conjugate Alkynylation of β-Aminoenones: Access to Chiral β-Alkynyl-β-Amino Carbonyl Derivatives

  摘要：

  Readily available potassium alkynyltrifluoroborates were used for organocatalytic asymmetric conjugate alkynylation of beta-enaminones. The interception of a modified binaphthol catalyst and in situ generated organodifluoroboranes proved important to access functionalized beta-alkynyl-beta-amino carbonyls and derivatives with improved chemo-reactivity and enantio-induction. Mechanistic studies revealed the impact of molecular sieves on efficiency and stereocontrol. The products undergo additional functionalization to yield a diverse set of valuable beta-alkynyl-beta-amino carbonyl scaffolds.

  DOI：

  10.1021/acs.orglett.0c02394
• 作为产物：
  描述：

  1-甲基苯并咪唑 在 正丁基锂 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 49.25h， 生成 3-(N,N-dimethylamino)-1-(1-methyl-1H-benzimidazol-2-yl)prop-2-en-1-one
  参考文献：
  名称：

  Organocatalytic Enantioselective Conjugate Alkynylation of β-Aminoenones: Access to Chiral β-Alkynyl-β-Amino Carbonyl Derivatives

  摘要：

  Readily available potassium alkynyltrifluoroborates were used for organocatalytic asymmetric conjugate alkynylation of beta-enaminones. The interception of a modified binaphthol catalyst and in situ generated organodifluoroboranes proved important to access functionalized beta-alkynyl-beta-amino carbonyls and derivatives with improved chemo-reactivity and enantio-induction. Mechanistic studies revealed the impact of molecular sieves on efficiency and stereocontrol. The products undergo additional functionalization to yield a diverse set of valuable beta-alkynyl-beta-amino carbonyl scaffolds.

  DOI：

  10.1021/acs.orglett.0c02394

文献信息

• One-Pot Synthesis of Enaminones Using Golds Reagent
  作者：Tamer S. Saleh、Mohamed A. Al-Omar、Hatem A. Abdel-Aziz

  DOI：10.2174/157017810791824793

  日期：2010.9.1

  Enaminones were efficiently prepared via modification for Gupton method, which depends on carrying out the latter procedure in one step reaction, avoiding the isolation of [3-(dimethylamino)-2-azaprop-2-en-1- ylidene]dimethylammonium chloride (Golds reagent) (5) which is prepared in situ from cyanuric chloride (4) then it reacts successfully with ketone 1a-j to produce the enaminones 3a-j in suitable yields. The modified method overcomes the drawbacks of the known methods for preparation of enaminones.

  通过对Gupton方法的改进，有效地制备了烯酰胺。这一过程依赖于在一步反应中进行，避免了对[3-(二甲基氨基)-2-氮杂丙-2-烯-1-亚基]二甲基铵氯化物（Golds试剂）（5）的分离，该试剂是通过氰尿酸氯（4）原位制备的，随后与酮1a-j成功反应，生成产率适宜的烯酰胺3a-j。改进的方法克服了已知烯酰胺制备方法的缺点。
• Kumar, Kishore; Hemasunder; Naidu, Indian Journal of Heterocyclic Chemistry, 2011, vol. 20, # 4, p. 393 - 398
  作者：Kumar, Kishore、Hemasunder、Naidu、Dubey

  DOI：——

  日期：——
• 2-Anilino-4-(benzimidazol-2-yl)pyrimidines – A multikinase inhibitor scaffold with antiproliferative activity toward cancer cell lines
  作者：Renate Determann、Jan Dreher、Knut Baumann、Lutz Preu、Peter G. Jones、Frank Totzke、Christoph Schächtele、Michael H.G. Kubbutat、Conrad Kunick

  DOI：10.1016/j.ejmech.2012.04.007

  日期：2012.7

  2-Anilino-4-(benzimidazol-2-yl)-pyrimidines, synthesized by reaction of a readily available benzimidazole-substituted enaminone with suitable arylguanidines, were shown to inhibit four cancer-related protein kinases (Aurora B, PLK1, FAK, and VEGF-R2). The most potent derivative exhibited antiproliferative activity for several cancer cell lines of the NCI in vitro cell line panel in submicromolar concentrations. Both the anilinopyrimidine structure and the substitution pattern at the aniline ring appear to be important for the protein kinase inhibitory activity. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Organocatalytic Enantioselective Conjugate Alkynylation of β-Aminoenones: Access to Chiral β-Alkynyl-β-Amino Carbonyl Derivatives
  作者：Jian-Fei Wang、Xin Meng、Chao-Huan Zhang、Chuan-Ming Yu、Bin Mao

  DOI：10.1021/acs.orglett.0c02394

  日期：2020.10.2

  Readily available potassium alkynyltrifluoroborates were used for organocatalytic asymmetric conjugate alkynylation of beta-enaminones. The interception of a modified binaphthol catalyst and in situ generated organodifluoroboranes proved important to access functionalized beta-alkynyl-beta-amino carbonyls and derivatives with improved chemo-reactivity and enantio-induction. Mechanistic studies revealed the impact of molecular sieves on efficiency and stereocontrol. The products undergo additional functionalization to yield a diverse set of valuable beta-alkynyl-beta-amino carbonyl scaffolds.