tert-butyl 4–(2-methoxybenzyl)piperazine-1-carboxylate | 872846-69-0

• 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: tert-butyl 4–(2-methoxybenzyl)piperazine-1-carboxylate
• 英文别名: Tert-butyl 4-[(2-methoxyphenyl)methyl]piperazine-1-carboxylate
• CAS: 872846-69-0
• 化学式: C₁₇H₂₆N₂O₃
• mdl: MFCD09953084
• 分子量: 306.405
• InChiKey: NWOMHGCDCSSYDD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.588
• 拓扑面积：
  42
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl 4–(2-methoxybenzyl)piperazine-1-carboxylate 在 N-甲基吗啉 、 盐酸 、 HATU 、 水 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 (3-(4-chlorophenyl)-1H-pyrazol-5-yl)(4-(2-methoxybenzyl)piperazin-1-yl)methanone
  参考文献：
  名称：

  Discovery of 3-aryl-5-acylpiperazinyl-pyrazoles as antagonists to the NK3 receptor

  摘要：

  A series of 3-aryl-5-acylpiperazinyl-pyrazoles (e.g., 3a-b) initially identified through a high-throughput screening campaign using the aequorin Ca2+ bioluminescence assay as novel, potent small molecule antagonists of the G protein-coupled human tachykinin NK3 receptor (hNK3-R) is described. Preliminary profiling revealed poor plasma and metabolic stability for these structures in rodents. Further optimization efforts resulted in analogs with improved potency, stability, and pharmacokinetic properties as well as good brain permeability, for example, compounds 26 and 42. Unexpected cytotoxicity was observed in such N-Me pyrazole structures as compounds 41-42. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.033
• 作为产物：
  描述：

  邻甲氧基苯甲醛 、 N-Boc-哌嗪 在 苯硅烷 、 二丁基二氯化锡 作用下， 以 四氢呋喃 为溶剂， 反应 0.12h， 以69%的产率得到tert-butyl 4–(2-methoxybenzyl)piperazine-1-carboxylate
  参考文献：
  名称：

  Microwave-Accelerated Methodology for the Direct Reductive Amination of Aldehydes

  摘要：

  [GRAPHICS]An improved procedure for the direct reductive amination of aldehydes was developed which uses dibutyltin dichloride as catalyst in the presence of phenylsilane as reductant. Rapid reaction is promoted by the use of microwave conditions with anilines, secondary and primary amines being suitable reactants.

  DOI：

  10.1021/ol0522844

文献信息

• 10.1080/14756366.2024.2353711
  作者：Wu, Tingting、Cheng, Hu、Sima, Lijie、Wang, Zhongyuan、Ouyang, Weiwei、Wang, Jianta、Hou, Yunlei、Zhao, Dongsheng、Liao, Weike、Hu, Chujiao

  DOI：10.1080/14756366.2024.2353711

  日期：——

  The PD-1/PD-L1 pathway is considered as one of the most promising immune checkpoints in tumour immunotherapy. However, researchers are faced with the inherent limitations of antibodies, driving the...

  PD-1/PD-L1 通路被认为是肿瘤免疫治疗中最有前途的免疫检查点之一。然而，研究人员面临着抗体的固有局限性，推动了...
• Microwave-Accelerated Methodology for the Direct Reductive Amination of Aldehydes
  作者：Jussi J. Kangasmetsä、Tony Johnson

  DOI：10.1021/ol0522844

  日期：2005.12.1

  [GRAPHICS]An improved procedure for the direct reductive amination of aldehydes was developed which uses dibutyltin dichloride as catalyst in the presence of phenylsilane as reductant. Rapid reaction is promoted by the use of microwave conditions with anilines, secondary and primary amines being suitable reactants.
• Discovery of 3-aryl-5-acylpiperazinyl-pyrazoles as antagonists to the NK3 receptor
  作者：Hamid R. Hoveyda、Marie-Odile Roy、Sebastien Blanc、Sophie Noël、Joseph M. Salvino、Mark A. Ator、Graeme Fraser

  DOI：10.1016/j.bmcl.2011.02.033

  日期：2011.4

  A series of 3-aryl-5-acylpiperazinyl-pyrazoles (e.g., 3a-b) initially identified through a high-throughput screening campaign using the aequorin Ca2+ bioluminescence assay as novel, potent small molecule antagonists of the G protein-coupled human tachykinin NK3 receptor (hNK3-R) is described. Preliminary profiling revealed poor plasma and metabolic stability for these structures in rodents. Further optimization efforts resulted in analogs with improved potency, stability, and pharmacokinetic properties as well as good brain permeability, for example, compounds 26 and 42. Unexpected cytotoxicity was observed in such N-Me pyrazole structures as compounds 41-42. (C) 2011 Elsevier Ltd. All rights reserved.