(2R,5R)-2,5-dibenzylpiperazine

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (2R,5R)-2,5-dibenzylpiperazine
• 英文别名: (2R,5R)-2,5-Dibenzylpiperazine
• 化学式: C₁₈H₂₂N₂
• 分子量: 266.386
• InChiKey: MHZXGSQZAQYQPG-QZTJIDSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  24.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 (2R,5R)-2,5-dibenzylpiperazine 在 甲酸 作用下， 以 水 为溶剂， 反应 0.5h， 以78%的产率得到(2R,5R)-2,5-dibenzyl-1,4-dimethylpiperazine
  参考文献：
  名称：

  Preventing Candida albicans biofilm formation using aromatic-rich piperazines

  摘要：

  The global increase in microbial resistance is an imminent threat to public health. Effective treatment of infectious diseases now requires new antimicrobial therapies. We report herein the discovery of aromatic-rich piperazines that inhibit biofilm formation by C. albicans. 22 piperazines, including 16 novel ones, were prepared efficiently using a combination of solid- and solution phase synthesis. The most potent compound prevents morphological switching under several hypha-inducing conditions and reduces C. albicans' ability to adhere to epithelial cells. These processes are essential to the development of Candida biofilms, which are associated with its increased resistance to immune defenses and antifungal agents.

  DOI：

  10.1016/j.bmc.2020.115810
• 作为产物：
  描述：

  Boc-D-苯丙氨酸 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 、 N,N'-二异丙基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 (2R,5R)-2,5-dibenzylpiperazine
  参考文献：
  名称：

  Novel chiral N,N′-dimethyl-1,4-piperazines with metal binding abilities

  摘要：

  With the objective of developing novel chiral ligands, we report an efficient strategy to prepare chiral N,N-dimethyl-1,4-piperazines, six-member heterocyclic molecules that possess metal binding features. We prepared and characterized 18 piperazines, and evaluated their ability to complex different mono- and divalent metals, using a rapid picrate extraction technique. Some newly prepared diamine ligands were used in diethylzinc alkylation of aryl aldehydes. Yields increased significantly in the presence of the diamine ligands, though enantioselectivity was low. The results demonstrate the validity of the approach for preparing and identifying useful chiral diamine ligands. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.08.051

文献信息

• Novel chiral N,N′-dimethyl-1,4-piperazines with metal binding abilities
  作者：Christopher Bérubé、Sébastien Cardinal、Pierre-Luc Boudreault、Xavier Barbeau、Nicolas Delcey、Martin Giguère、Dave Gleeton、Normand Voyer

  DOI：10.1016/j.tet.2015.08.051

  日期：2015.10

  With the objective of developing novel chiral ligands, we report an efficient strategy to prepare chiral N,N-dimethyl-1,4-piperazines, six-member heterocyclic molecules that possess metal binding features. We prepared and characterized 18 piperazines, and evaluated their ability to complex different mono- and divalent metals, using a rapid picrate extraction technique. Some newly prepared diamine ligands were used in diethylzinc alkylation of aryl aldehydes. Yields increased significantly in the presence of the diamine ligands, though enantioselectivity was low. The results demonstrate the validity of the approach for preparing and identifying useful chiral diamine ligands. (C) 2015 Elsevier Ltd. All rights reserved.
• Catalytic Hydrogenation of 2,5-Dialkylpyrazines and 3,6-Dialkyl-2-hydroxypyrazines
  作者：Akihiro Ohta、Yukari Okuwaki、Tsuyoshi Komaru、Mieko Hisatome、Yasushi Yoshida、Jun Aizawa、Yumi Nakano、Hiroko Shibata、Takuya Miyazaki、Tokuhiro Watanabe

  DOI：10.3987/r-1987-10-2691

  日期：——
• Preventing Candida albicans biofilm formation using aromatic-rich piperazines
  作者：Gaëlle Simon、Christopher Bérubé、Pierre-Alexandre Paquet-Côté、Daniel Grenier、Normand Voyer

  DOI：10.1016/j.bmc.2020.115810

  日期：2020.12

  The global increase in microbial resistance is an imminent threat to public health. Effective treatment of infectious diseases now requires new antimicrobial therapies. We report herein the discovery of aromatic-rich piperazines that inhibit biofilm formation by C. albicans. 22 piperazines, including 16 novel ones, were prepared efficiently using a combination of solid- and solution phase synthesis. The most potent compound prevents morphological switching under several hypha-inducing conditions and reduces C. albicans' ability to adhere to epithelial cells. These processes are essential to the development of Candida biofilms, which are associated with its increased resistance to immune defenses and antifungal agents.