1-(2,4,6-三甲基苄基)哌嗪 | 41717-26-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(2,4,6-三甲基苄基)哌嗪
• 英文名称: 1-(2,4,6-trimethylbenzyl)-piperazine
• 英文别名: 1-(2,4,6-Trimethylbenzyl)piperazine；1-[(2,4,6-trimethylphenyl)methyl]piperazine
• CAS: 41717-26-4
• 化学式: C₁₄H₂₂N₂
• mdl: MFCD03094587
• 分子量: 218.342
• InChiKey: FOERNUXLFALRDN-UHFFFAOYSA-N

物化性质

• 熔点：
  88-98 °C (lit.)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.571
• 拓扑面积：
  15.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• 海关编码：
  2933599090
• WGK Germany：
  3
• 危险标志：
  GHS07
• 危险性描述：
  H315,H319,H335
• 危险性防范说明：
  P261,P305 + P351 + P338

反应信息

• 作为反应物：
  描述：

  1-(2,4,6-三甲基苄基)哌嗪 在 platinum(IV) oxide 氢气 、 sodium ascorbate 、 柠檬酸 作用下， 以 乙醇 为溶剂， 反应 14.08h， 生成 16,17,18,19,28,29-hexahydro-3-rifamycin SV
  参考文献：
  名称：

  Hypolipidemic activity of rifamycin derivatives

  摘要：

  Series of 3-piperidinyl- and 3-piperazinylrifamycins and to a certain extent 3-hydrazonorifamycins all bearing lipophilic side chains were found to exert potent hypolipidemic activity in lowering both serum cholesterol and LDL-cholesterol in rats. Starting from 3-[N'-(2,4,6-trimethylbenzyl)-N-piperazinyl]rifamycin SV (compound 25), a series of derivatives were synthesized with the aim of dissociating the hypolipidemic from the antibacterial activity, leading to the 8-O,N-dipivaloyl derivative of 25 (compound 48), which is devoid of any antibacterial activity but shows about 50-60% reduction of LDL-cholesterol and 20-30% reduction of serum cholesterol at a dose of 10 mg/kg. Compound 48 was selected for further pharmacological evaluation.

  DOI：

  10.1021/jm00164a013
• 作为产物：
  描述：

  哌嗪 、 2,4,6-三甲基氯苄 以 四氢呋喃 为溶剂， 反应 4.0h， 以94.3%的产率得到1-(2,4,6-三甲基苄基)哌嗪
  参考文献：
  名称：

  Exploration of (S)-3-aminopyrrolidine as a potentially interesting scaffold for discovery of novel Abl and PI3K dual inhibitors

  摘要：

  Based on the literature-reported compensatory effect of PI3K on Abl inhibition and the improved preclinical effect of drug combination of Abl and PI3K inhibitors, a series of compounds bearing novel scaffold of (S)-3-aminopyrrolidine was identified as Abl and PI3K dual inhibitors through support vector machine screening tool, which were subsequently synthesized and tested. Most compounds demonstrated promising cytoxicity against a CML leukemia cell-line K562 and moderate inhibition against Abl and PI3K kinases. These compounds induced no apoptosis in K562 cell-line, suggesting that their cytotoxic activities are unlikely duo to other known anti-CML mechanisms. Molecular docking study further showed that the compound 5k could bind with both Abl and PI3K, but the weaker binding with Abl compared to Imatinib is consistent with its low kinase inhibitory rates. These plus literature-reported evidences suggest that the promising cytotoxic effect of our novel compounds might be due to the collective effect of Abl and PI3K inhibition. (c) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.01.020

文献信息

• Synthesis of Aza-acyclic Nucleoside Libraries of Purine, Pyrimidine, and 1,2,4-Triazole
  作者：Vibha Pathak、Ashish K. Pathak、Robert C. Reynolds

  DOI：10.1021/acscombsci.8b00136

  日期：2019.3.11

  of the Pilot Scale Library Program of the NIH Roadmap Initiative, a new library of propan-1-amine containing aza acyclic nucleosides was designed and prepared, and we now report a diverse set of 157 purine, pyrimidine, and 1,2,4-triazole-N-acetamide analogues. These new nucleoside analogues were prepared in a parallel high throughput solution-phase format. A set of diverse amines was reacted with several

  在美国国立卫生研究院路线图计划的试点图书馆计划的主持下，设计并制备了一个新的含有丙-1-胺的氮杂无环核苷图书馆，我们现在报告了157种嘌呤，嘧啶和1,2 ，4-三唑-N-乙酰胺类似物。这些新的核苷类似物以平行的高通量溶液相形式制备。一组不同的胺与几个核碱基N反应-丙醛利用与三乙酰氧基硼氢化钠偶合的还原胺化来生成一个小的且多样化的氮杂无环核苷文库。所有反应均在惰性气氛下使用24孔反应模块和自动试剂分配平台进行。使用固体样品上样的预装柱和硅胶柱在自动化系统上纯化最终目标。所有化合物均通过NMR和HRMS进行表征，并通过HPLC分析纯度，然后提交分子库小分子储存库（MLSMR）。通过分子图书馆探针生产中心网络（MLPCN）进行的初步筛选显示了多种有趣的生物学活动。
• INHIBITORS OF STEAROYL-COA DESATURASE
  申请人：Gillespie Paul

  公开号：US20090149466A1

  公开（公告）日：2009-06-11

  Provided herein are compounds of the formula (I): as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful for the treatment of diseases such as, for example, obesity.

  提供以下式(I)化合物： 以及药用可接受的盐，其中取代基如说明书中所披露。这些化合物以及包含它们的药物组合物可用于治疗诸如肥胖等疾病。
• Solution-Phase Parallel Synthesis of Acyclic Nucleoside Libraries of Purine, Pyrimidine, and Triazole Acetamides
  作者：Ashish K. Pathak、Vibha Pathak、Robert C. Reynolds

  DOI：10.1021/co500067c

  日期：2014.9.8

  produced and report herein a diverse library of 181 purine, pyrimidine, and 1,2,4-triazole-N-acetamide analogues which were prepared in a parallel high throughput solution-phase reaction format. A set of assorted amines were reacted with several nucleic acid N-acetic acids utilizing HATU as the coupling reagent to produce diverse acyclic nucleoside N-acetamide analogues. These reactions were performed

  使用高通量筛选技术，分子多样性在针对表型或基于酶的靶标的现代药物发现中起着关键作用。在美国国立卫生研究院路线图计划的试点图书馆计划的主持下，我们生产并报告了181种嘌呤，嘧啶和1,2,4-三唑-N-乙酰胺类似物的多样化文库，它们以平行的高通量制备溶液相反应形式。利用HATU作为偶联剂，将一组各种胺与几种核酸N-乙酸反应，以产生多种无环核苷N-乙酰胺类似物。这些反应是在惰性气氛下使用24孔反应块和自动试剂分配平台进行的。使用自动装载固体样品的预装柱和预装硅胶柱，在自动纯化系统上纯化目标化合物。所有化合物均通过NMR和HRMS进行表征，并通过HPLC分析纯度，然后提交至NIH的分子库小分子储存库（MLSMR）。通过分子图书馆探针生产中心网络（MLPCN）程序进行的初步筛选表明，几种类似物均表现出多样而有趣的生物学活性。
• Palladium-Catalyzed Synthesis of 2-(Aminomethyl)indoles from Ethyl 3-(<i>o</i>-Trifluoroacetamidophenyl)-1-propargyl Carbonate
  作者：Ilaria Ambrogio、Sandro Cacchi、Giancarlo Fabrizi

  DOI：10.1021/ol060499n

  日期：2006.5.1

  [reaction: see text] The palladium-catalyzed reaction of ethyl 3-(o-trifluoroacetamidophenyl)-1-propargyl carbonate with piperazines in the presence of Pd(PPh(3))(4) in THF at 80 degrees C affords 2-(piperazin-1-ylmethyl)indoles in excellent yields. Good to excellent yields are also obtained with other secondary amines.

  [反应：参见正文]在THF中，在Pd（PPh（3））（4）存在下，钯3-催化碳酸3-（邻三氟乙酰氨基苯基）-1-炔丙基碳酸酯与哌嗪的反应得到2- （哌嗪-1-基甲基）吲哚的产率高。用其他仲胺也能获得良好至优异的产率。
• 3-(o-Trifluoroacetamidoaryl)-1-propargylic esters: common intermediates for the palladium-catalyzed synthesis of 2-aminomethyl-, 2-vinylic, and 2-alkylindoles
  作者：Ilaria Ambrogio、Sandro Cacchi、Giancarlo Fabrizi、Alessandro Prastaro

  DOI：10.1016/j.tet.2009.06.113

  日期：2009.10

  3-(o-Trifluoroacetamidoaryl)-1-propargylic esters have been used as common synthetic intermediates for the preparation of a variety of 3-unsubstituted 2-substituted indoles. Treating ethyl 3-(o-trifluoroacetamidoaryl)-1-propargylic carbonates unsubstituted or containing an aryl substituent at the propargylic carbon with piperazines and Pd(PPh3)4 in THF at 80 °C affords 2-(piperazin-1-ylmethyl)indoles in excellent yields

  3-（邻-三氟乙酰氨基芳基）-1-炔丙基酯已被用作制备各种3-未取代的2-取代的吲哚的常用合成中间体。在80°C下用哌嗪和Pd（PPh 3）4在THF中处理未取代的或在炔丙基碳上包含芳基取代基的3-（邻-三氟乙酰氨基芳基）-1-丙炔碳酸酯，得到2-（哌嗪-1-基甲基）吲哚高产。用其他仲胺也可获得2-氨基甲基吲哚的良好至优异的产率。在炔丙基碳上带有烷基取代基的乙基3-（邻-三氟乙酰氨基芳基）-1-炔丙基碳酸酯和乙基3-（o在炔丙基碳处被二取代的-（三氟乙酰氨基芳基）-1-炔丙基乙酸酯在80°C下的Pd（OAc）2 / PPh 3组合和Et 3 N在THF中的生成2-乙烯基吲哚。2-乙烯基吲哚的形成具有很强的立体选择性，至少在我们研究的底物上会生成反式乙烯基衍生物。在80°C下于MeCN中存在甲酸，Et 3 N和Pd（PPh 3）4的情况下，乙基3-（邻三氟乙酰胺基芳基）-1-炔丙基碳酸酯能以优异的产率获得2-烷基吲哚。