1-(4-甲氧基苄基)-4-甲基哌嗪 | 414879-57-5

• 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-(4-甲氧基苄基)-4-甲基哌嗪
• 英文名称: N-(4-methoxybenzyl)-N'-methylpiperazine
• 英文别名: 1-(4-methoxybenzyl)-4-methylpiperazine；4-(4-methoxybenzyl)-1-methylpiperazine；1-[(4-methoxyphenyl)methyl]-4-methylpiperazine
• CAS: 414879-57-5
• 化学式: C₁₃H₂₀N₂O
• mdl: MFCD01466576
• 分子量: 220.315
• InChiKey: VRBZXMTXVNIWQC-UHFFFAOYSA-N

物化性质

• 沸点：
  313.6±27.0 °C(Predicted)
• 密度：
  1.044±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.538
• 拓扑面积：
  15.7
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933599090

反应信息

• 作为反应物：
  描述：

  3-苯基-1,2,4-恶二唑 、 1-(4-甲氧基苄基)-4-甲基哌嗪 在 碘 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以75 %的产率得到5-(4-methylpiperazin-1-yl)-3-phenyl-1,2,4-oxadiazole
  参考文献：
  名称：

  Tertiary Amines as Temporary Masked Secondary Amines: A Direct Access to 5-Dialkylamino-1,2,4-oxadiazoles from 1,2,4-Oxadiazol-5(4H)-ones

  摘要：

  A novel strategy utilizing tertiary amines as temporary masked secondary amines to synthesize 5-dialkylamino 1,2,4-oxadiazoles via Ph3P-I2 mediated amination of 1,2,4-oxadiazol-5(4H)-ones was developed. A one-step N-dealkylative functionalization of tertiary amines with the 1,2,4-oxadiazole ring enables a convenient access to diverse 5-amino-1,2,4-oxadiazoles. Additionally, orthogonally functionalized piperazine derivatives can be effectively constructed through site-selective reaction of 1,4-dialkylpiperazines or via a sequential N-functionalization of 1-methylpiperazine obviating laborious protection/deprotection steps.

  DOI：

  10.1055/s-0042-1751555
• 作为产物：
  描述：

  N-甲基哌嗪 在 palladium diacetate 、 caesium carbonate 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 49.0h， 生成 1-(4-甲氧基苄基)-4-甲基哌嗪
  参考文献：
  名称：

  Reinvestigation of Aminomethyltrifluoroborates and Their Application in Suzuki−Miyaura Cross-Coupling Reactions

  摘要：

  A reinvestigation into the chemical composition of potassium aminomethyltrifluoroborates is reported. These trifluoroborato salts have been reassigned as zwitterionic ammoniomethyltrifluoroborates. Minor adjustments to the previously disclosed reaction conditions are reported that permit a similar level of activity as nucleophiles in Suzuki-Miyaura cross-coupling reactions.

  DOI：

  10.1021/jo2001066

文献信息

• Aminomethylation via Cyclopalladated-Ferrocenylimine-Complexes-Catalyzed Suzuki-Miyaura Coupling of Aryl Halides with Potassium N,N-Dialkylaminomethyltrifluoroborates
  作者：Yangjie Wu、Yusheng Wu、Dapeng Zou、Hongmeng Cui、Lijin Qin、Jingya Li

  DOI：10.1055/s-0030-1259331

  日期：2011.2

  Using cyclopalladated ferrocenylimine complexes (1-3 mol%) as catalysts, the Suzuki-Miyaura coupling of potassium N,N-dialkylaminomethyltrifluoroborates with aryl and heteroaryl halides were carried out in a 10:1 THF-H2O mixture at 80 ˚C in the presence of Cs2CO3 (3.0 equiv) as base, giving the desired cross-coupling products in 14-87% yields. A variety of potassium alkyltrifluoroborates were also examined.

  使用环钯化二茂铁亚胺配合物（1-3摩尔%）作为催化剂，在Cs2CO3（3.0当量）作为碱的存在下，在80 ℃的10:1 THF-H2O混合物中，进行钾N,N-二烷基氨基甲基三氟硼酸盐与芳基和杂芳基卤化物的铃木-宫浦偶联反应，得到了所需的交叉偶联产物，产率为14-87%。还研究了各种烷基三氟硼酸钾。
• [EN] SUBSTITUTED PYRAZOLO[1,5-A]PYRIDINE COMPOUNDS AS RET KINASE INHIBITORS<br/>[FR] COMPOSÉS SUBSTITUÉS DE PYRAZOLO[1,5-A]PYRIDINES COMME INHIBITEURS DE LA KINASE RET
  申请人：ARRAY BIOPHARMA INC

  公开号：WO2017011776A1

  公开（公告）日：2017-01-19

  Provided herein are compounds of the General Formula I: and stereoisomers and pharmaceutically acceptable salts or solvates thereof, in which A, B, D, E, X1, X2, X3 and X4 have the meanings given in the specification, which are inhibitors of RET kinase and are useful in the treatment and prevention of diseases which can be treated with a RET kinase inhibitor, including diseases or disorders mediated by a RET kinase.

  本文提供了一般式I的化合物及其立体异构体和药用可接受的盐或溶剂，其中A、B、D、E、X1、X2、X3和X4的含义如规范中所述，这些化合物是RET激酶的抑制剂，可用于治疗和预防可以用RET激酶抑制剂治疗的疾病，包括由RET激酶介导的疾病或紊乱。
• Regioselective Borylation of the C–H Bonds in Alkylamines and Alkyl Ethers. Observation and Origin of High Reactivity of Primary C–H Bonds Beta to Nitrogen and Oxygen
  作者：Qian Li、Carl W. Liskey、John F. Hartwig

  DOI：10.1021/ja503676d

  日期：2014.6.18

  Borylation of aliphatic C-H bonds in alkylamines and alkyl ethers to form primary aminoalkyl and alkoxyalkyl boronate esters and studies on the origin of the regioselectivity of these reactions are reported. The products of these reactions can be used directly in Suzuki-Miyaura cross-coupling reactions or isolated as air-stable potassium trifluoroborate salts. Selective borylation of the terminal C-H

  报道了烷基胺和烷基醚中脂肪族 CH 键的硼化反应，形成伯氨基烷基和烷氧基烷基硼酸酯，并研究了这些反应的区域选择性起源。这些反应的产物可直接用于 Suzuki-Miyaura 交叉偶联反应或作为空气稳定的三氟硼酸钾盐分离。位置 β 的末端 CH 键选择性硼化为氧和氮，优先于其他末端 CH 键的硼化。实验研究和计算结果表明，CH 键断裂是当前硼化反应的速率决定步骤。在乙胺和醚的末端位置观察到的 CH 键的更高反应性是由于有吸引力的路易斯酸碱和氢键相互作用的结合，以及过渡态中典型的排斥性空间相互作用。在这种过渡态中，杂原子直接位于一个硼基配体的硼原子上方，在弱路易斯酸和路易斯碱之间产生稳定的相互作用，并且底物的一系列 CH 键位于硼基配体的氧原子附近，参与一组弱的 CH···O 相互作用，导致形成主要产物的过渡态显着稳定。
• Scope of Aminomethylations via Suzuki−Miyaura Cross-Coupling of Organotrifluoroborates
  作者：Gary A. Molander、Paul E. Gormisky、Deidre L. Sandrock

  DOI：10.1021/jo800183q

  日期：2008.3.1

  previously reported the Suzuki−Miyaura reaction of N,N-dialkylaminomethyltrifluoroborates with aryl bromides. Herein, we report a further investigation of the scope and limitations of this palladium-catalyzed aminomethylation reaction. Aryl chlorides, iodides, and triflates coupled in good to excellent yields to give N,N-dialkylbenzylic amines. The aminomethylation of alkenyl bromides was also examined.

  我们先前报道了N，N-二烷基氨基甲基三氟硼酸酯与芳基溴化物的Suzuki-Miyaura反应。本文中，我们报告了对该钯催化的氨基甲基化反应的范围和局限性的进一步研究。芳基氯化物，碘化物和三氟甲磺酸酯以良好至优异的收率偶联，得到N，N-二烷基苄基胺。还检查了烯基溴化物的氨基甲基化。
• [EN] SUBSTITUTED PYRAZOLO[1,5-a]PYRAZINE COMPOUNDS AS RET KINASE INHIBITORS<br/>[FR] COMPOSÉS DE PYRAZOLO[1,5-A]PYRAZINE SUBSTITUÉS UTILISÉS EN TANT QU'INHIBITEURS DE LA KINASE RET
  申请人：ANDREWS STEVEN W

  公开号：WO2018136661A1

  公开（公告）日：2018-07-26

  Provided herein are compounds of the Formula I: and stereoisomers and pharmaceutically acceptable salts or solvates thereof, in which A, B, D, E, X1, X2, X3 and X4 have the meanings given in the specification, which are inhibitors of RET kinase and are useful in the treatment and prevention of diseases which can be treated with a RET kinase inhibitor, including diseases or disorders mediated by a RET kinase.

  本文提供了Formula I的化合物及其立体异构体和药学上可接受的盐或溶剂，其中A、B、D、E、X1、X2、X3和X4在规范中给出的含义，这些化合物是RET激酶的抑制剂，可用于治疗和预防可以用RET激酶抑制剂治疗的疾病，包括由RET激酶介导的疾病或紊乱。