(2S,5S)-2,5-dibenzyl-1,4-dimethylpiperazine | 81536-08-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (2S,5S)-2,5-dibenzyl-1,4-dimethylpiperazine
• CAS: 81536-08-5
• 化学式: C₂₀H₂₆N₂
• 分子量: 294.44
• InChiKey: HGCOAWJFJGNIBD-PMACEKPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  环二(N-甲基苯丙氨酸) 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 以80%的产率得到(2S,5S)-2,5-dibenzyl-1,4-dimethylpiperazine
  参考文献：
  名称：

  用于对映选择性合成环状二肽的 3,6-二亚烷基-2,5-二酮哌嗪的红外催化双不对称氢化

  摘要：

  Ir/spiro[4,4]-1,6-壬二烯基膦-恶唑啉配体 (SpinPHOX) 配合物催化 3,6-二亚烷基-1,4-二甲基哌嗪-2,5-二酮的双不对称氢化开发，提供高效和实用的途径以高产率获得各种手性 3,6-二取代-2,5-二酮哌嗪，具有独特的顺式非对映选择性和优异的对映选择性（>99% de，高达 98% ee）。该协议的合成效用已在 6a 的克级合成和手性产品 8、14 和 17 以及 2-丁烯基桥连双环二酮哌嗪 10 和羟基二酮哌嗪 11 的有效构建中得到证明。 使用类似的非手性 Ir 催化剂，对映纯单氢化中间体 7a 的氢化得到 cis-6a 作为唯一的产物，表明标题转化的第二步氢化是手性底物控制的过程。5a 的不对称加氢 (AH) 的反应曲线研究表明，单加氢中间体 7a 的浓度在加氢过程中保持在低水平 (<8%)。5a 到 6a 的加氢速度明显快于其半加氢中间体 (S)-7

  DOI：

  10.1021/jacs.9b02920
• 作为试剂：
  描述：

  diethylzinc 、 4-甲氧基苯甲醛 在 (2S,5S)-2,5-dibenzyl-1,4-dimethylpiperazine 作用下， 以 甲苯 为溶剂， 反应 48.25h， 以5%的产率得到
  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

• Enantioselective Henry reaction catalyzed by C2-symmetric chiral diamine–copper(II) complex
  作者：Sermadurai Selvakumar、Dhanasekaran Sivasankaran、Vinod K. Singh

  DOI：10.1039/b904254g

  日期：——

  A copper(II) complex of C2-symmetric diamine has been proved to be an efficient catalyst for the enantioselective Henry reaction between nitroalkanes and various aldehydes to provide β-hydroxy nitroalkanes in high yields (up to 97%), moderate diastereoselectivities (up to 71:29) and excellent enantiomeric excesses (up to 96%). The chiral nitroaldol adduct obtained has been further converted into chiral

  事实证明，C 2对称二胺的铜（II）络合物是硝基链烷烃与各种醛之间对映选择性亨利反应的有效催化剂，以高产率（高达97％），中等非对映选择性（高达90％以上）提供β-羟基硝基链烷烃。至71:29）和出色的对映体过量（高达96％）。所获得的手性硝基醛醇加合物在几个步骤中已进一步转化为手性氮丙啶。
• (2S,5S)-2,5-dibenzyl-1,4-dimethylpiperazine, a novel alkaloid from zanthoxylum arborescens
  作者：Jonas A. Grina、Frank R. Stermitz

  DOI：10.1016/s0040-4039(01)92474-8

  日期：——

  The isolation and structure determination of (2S,5S)-2,5-dibenzyl-1,4-dimethylpiperazine (), a new alkaloid biogenetically related to L-phenylalanine diketopiperazine, is described.

  描述了（2S，5S）-2,5-二苄基-1,4-二甲基哌嗪（）的分离和结构测定，该新生物碱与L-苯丙氨酸二酮哌嗪具有生物相关性。
• 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.
• Organic chemistry of L-tyrosine. 1. General synthesis of chiral piperazines from amino acids
  作者：Michael E. Jung、John C. Rohloff

  DOI：10.1021/jo00224a051

  日期：1985.11
• 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：——