1-cyclododecyl-2-hydroxy-2-(3-nitrophenyl)-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-4-ium bromide | 1042275-13-7

• 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-cyclododecyl-2-hydroxy-2-(3-nitrophenyl)-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-4-ium bromide
• 英文别名: 1-cyclododecyl-2-(3-nitrophenyl)-3H-imidazo[1,2-a]pyrimidin-4-ium-2-ol;bromide
• CAS: 1042275-13-7
• 化学式: Br*C₂₄H₃₃N₄O₃
• 分子量: 505.455
• InChiKey: AJVMOUQMRWVWHG-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.62
• 重原子数：
  32
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  86.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-cyclododecyl-2-hydroxy-2-(3-nitrophenyl)-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-4-ium bromide 在 一水合肼 作用下， 以 乙腈 为溶剂， 反应 0.17h， 以75%的产率得到cyclododecyl[4-(3-nitrophenyl)-1H-imidazol-2-yl]amine
  参考文献：
  名称：

  A Divergent Synthesis of Substituted 2-Aminoimidazoles from 2-Aminopyrimidines

  摘要：

  A new divergent and efficient synthesis of substituted 2-aminoimidazoles 5 and 6 has been developed starting from the readily available 2-aminopyrimidines 1 and alpha-broinocarbonyl compounds 2, Using conventional heating or microwave irradiation. Thus, the cleavage of 1,2,3-substituted imidazo[1,2-a]pyrimidin-1 -iumsalts 4 with hydrazine or secondary amines led to 1,4,5-trisubstituted 2-aminoimidazoles 5, when the hydrazinolysis of 2-hydroxy-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-4-ium salts 3, followed by a novel Dimroth-type rearrangement, resulted in formation of 2-amino-1H-imidazoles 6. The relevant pathway of transformations was identified by characterization of the intermediates.

  DOI：

  10.1021/jo8008758
• 作为产物：
  描述：

  环十二烷基(嘧啶-2-基)胺 、 2-溴-3'-硝基苯乙酮 在 4-二甲氨基吡啶 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以68%的产率得到1-cyclododecyl-2-hydroxy-2-(3-nitrophenyl)-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-4-ium bromide
  参考文献：
  名称：

  A Divergent Synthesis of Substituted 2-Aminoimidazoles from 2-Aminopyrimidines

  摘要：

  A new divergent and efficient synthesis of substituted 2-aminoimidazoles 5 and 6 has been developed starting from the readily available 2-aminopyrimidines 1 and alpha-broinocarbonyl compounds 2, Using conventional heating or microwave irradiation. Thus, the cleavage of 1,2,3-substituted imidazo[1,2-a]pyrimidin-1 -iumsalts 4 with hydrazine or secondary amines led to 1,4,5-trisubstituted 2-aminoimidazoles 5, when the hydrazinolysis of 2-hydroxy-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-4-ium salts 3, followed by a novel Dimroth-type rearrangement, resulted in formation of 2-amino-1H-imidazoles 6. The relevant pathway of transformations was identified by characterization of the intermediates.

  DOI：

  10.1021/jo8008758

文献信息

• COMPOUNDS, COMPOSITIONS AND METHODS FOR CONTROLLING BIOFILMS
  申请人：Katholieke Universiteit Leuven, K.U. Leuven R&D

  公开号：EP2513064A2

  公开（公告）日：2012-10-24
• COMPOUNDS, COMPOSITIONS, AND METHODS FOR CONTROLLING BIOFILMS
  申请人：De Keersmaecker Sigrid

  公开号：US20130029981A1

  公开（公告）日：2013-01-31

  The invention relates to substituted 2-aminoimidazoles and their imidazo[1,2- a ]pyrimidinium salts precursors being active against biofilm formation. The invention also relates to imidazo[1,2- a ]pyrimidinium salts bearing an azidoalkyl substituent, and to substituted 2-aminoimidazoles wherein the amino group bears a terminal heterocyclic group such as a triazolyl group which are formed through azide-alkyne Huisgen cycloaddition starting from said imidazo[1,2- a ]pyrimidinium salts bearing an azidoalkyl substituent. The invention also relates to a class of N-(azidoalkyl)pyrimidin-2-amines useful as starting materials for the synthesis of said imidazo[1,2- a ]pyrimidinium salts bearing an azidoalkyl substituent. The invention also relates to antimicrobial compositions that include a microbial biofilm formation inhibiting amount of such substituted 2-aminoimidazoles or imidazo[1,2- a ]pyrimidinium salts in combination with excipients. Methods for inhibiting or controlling microbial biofilm formation in a plant, a body part of a human or an animal, or a surface with which a human or an animal may come into contact are also disclosed.
• US8906915B2
  申请人：——

  公开号：US8906915B2

  公开（公告）日：2014-12-09
• [EN] COMPOUNDS, COMPOSITIONS AND METHODS FOR CONTROLLING BIOFILMS<br/>[FR] COMPOSÉ, COMPOSITIONS ET PROCÉDÉS DE LUTTE CONTRE LES BIOFILMS
  申请人：UNIV LEUVEN KATH

  公开号：WO2011080132A2

  公开（公告）日：2011-07-07

  This invention relates to substituted 2-aminoimidazoles and their imidazo[1,2- a]pyrimidinium salts precursors being active against biofilm formation. The present invention also relates to antimicrobial compositions comprising a microbial biofilm formation inhibiting amount of such substituted 2-aminoimidazoles or imidazo[1,2- a]pyrimidinium salts in combination with excipients. The present invention also relates to methods for inhibiting or controlling microbial biofilm formation in a plant, a body part of a human or an animal, or a surface with which a human or an animal may come into contact.
• A Divergent Synthesis of Substituted 2-Aminoimidazoles from 2-Aminopyrimidines
  作者：Denis S. Ermolat’ev、Erik V. Van der Eycken

  DOI：10.1021/jo8008758

  日期：2008.9.1

  A new divergent and efficient synthesis of substituted 2-aminoimidazoles 5 and 6 has been developed starting from the readily available 2-aminopyrimidines 1 and alpha-broinocarbonyl compounds 2, Using conventional heating or microwave irradiation. Thus, the cleavage of 1,2,3-substituted imidazo[1,2-a]pyrimidin-1 -iumsalts 4 with hydrazine or secondary amines led to 1,4,5-trisubstituted 2-aminoimidazoles 5, when the hydrazinolysis of 2-hydroxy-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-4-ium salts 3, followed by a novel Dimroth-type rearrangement, resulted in formation of 2-amino-1H-imidazoles 6. The relevant pathway of transformations was identified by characterization of the intermediates.