(2S,5S)-2-Isobutyl-5-isopropylpiperazine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: (2S,5S)-2-Isobutyl-5-isopropylpiperazine
• 英文别名: (2R,5R)-2-(2-methylpropyl)-5-propan-2-ylpiperazine
• 化学式: C₁₁H₂₄N₂
• 分子量: 184.325
• InChiKey: ATKITPGKWBGUQL-MNOVXSKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.62
• 重原子数：
  13.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  24.06
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 (2S,5S)-2-Isobutyl-5-isopropylpiperazine 在 甲酸 作用下， 以 水 为溶剂， 反应 0.5h， 生成 (2R,5R)-2-isobutyl-5-isopropyl-1,4-dimethylpiperazine
  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
• 作为产物：
  描述：

  BOC-D-亮氨酸 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 (2S,5S)-2-Isobutyl-5-isopropylpiperazine
  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

• Solution Structure of a Dilithiumamide/Diethylzinc Heterocomplex that Catalyzes Asymmetric Alkylation Reactions
  作者：Johan Eriksson、Per I. Arvidsson、Öjvind Davidsson

  DOI：10.1002/(sici)1521-3765(19990802)5:8<2356::aid-chem2356>3.0.co;2-k

  日期：1999.8.2

  The catalytic complex between diethylzinc and the lithium salt of the chiral piperazine, (2S,5S)-2-isobutyl-5-isopropylpiperazine (1) in THF was investigated by NMR spectroscopy. The lithium salt of 1 was found to undergo East chair-twisted boat-chair conformational exchange. However, upon addition of one equivalent of diethylzinc this process was found to slow down on the NMR timescale, The piperazine ring in 1 adopts a boat conformation in which the zinc bridges the two amide nitrogens in 1. Small additions of a substrate, for example benzaldehyde, resulted in a dramatic increase of the chair-twisted boat-chair conformational exchange, as seen in the NMR spectra.
• 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.