(4-benzylpiperazin-1-yl)(phenyl)methanone | 63991-67-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4-benzylpiperazin-1-yl)(phenyl)methanone
• 英文别名: Piperazine, 1-benzoyl-4-benzyl-；(4-benzylpiperazin-1-yl)-phenylmethanone
• CAS: 63991-67-3
• 化学式: C₁₈H₂₀N₂O
• mdl: MFCD00419057
• 分子量: 280.37
• InChiKey: VFSAEAGKVBCUNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.277
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4-benzylpiperazin-1-yl)(phenyl)methanone 在 palladium on activated charcoal 甲酸铵 作用下， 以 甲醇 为溶剂， 反应 8.0h， 以71%的产率得到1-苯甲酰哌嗪
  参考文献：
  名称：

  Structure–activity relationship studies on unifiram (DM232) and sunifiram (DM235), two novel and potent cognition enhancing drugs

  摘要：

  Structure-activity relationships on two novel potent cognition enhancing drugs, unifiram (DM232, 1) and sunifiram (DM235, 2), are reported. Although none of the compounds synthesised reached the potency of the parent drugs, some fairly active compounds have been identified that may represent new leads to develop other cognition enhancing drugs. An interesting result of this research is the identification of two compounds (13 and 14) that are endowed with amnesing activity (the opposite of the activity of the original molecules) and are nearly equipotent to scopolamine. Moreover, two compounds of the series (5 and 6) were found endowed with analgesic activity on a rat model of neuropathic pain at the dose of 1 mg/kg. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.10.025
• 作为产物：
  描述：

  4-苄基-1-(三氟乙酰基)哌嗪 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 (4-benzylpiperazin-1-yl)(phenyl)methanone
  参考文献：
  名称：

  叔苄胺与酰氯的轻度N-脱烷基作用：在固相化学中的应用

  摘要：

  对于溶液和固相都描述了用酰氯温和，容易地裂解适当取代的叔苄胺。

  DOI：

  10.1016/s0040-4039(98)00584-x

文献信息

• Direct reductive amination of carbonyl compounds using bis(triphenylphosphine) copper(I) tetrahydroborate
  作者：Mayur J. Bhanushali、Nitin S. Nandurkar、Malhari D. Bhor、Bhalchandra M. Bhanage

  DOI：10.1016/j.tetlet.2006.12.037

  日期：2007.2

  A direct reductive amination protocol for aldehydes/ketones using bis(triphenylphosphine) copper(I) tetrahydroborate as a novel reducing agent in the presence of sulfamic acid has been developed. The reagent chemoselectively reduces the imine moiety and does not affect other reducible functionalities such as chloro, nitro, cyano and methoxy.

  已经开发了在氨基磺酸存在下使用双（三苯基膦）四氢硼酸铜（I）作为新型还原剂的醛/酮直接还原胺化方案。该试剂化学选择性地还原亚胺部分，并且不影响其他可还原的官能团，例如氯，硝基，氰基和甲氧基。
• Aerobic Oxidative Amidation of Aromatic and Cinnamic Aldehydes with Secondary Amines by CuI/2-Pyridonate Catalytic System
  作者：Mingwen Zhu、Ken-ichi Fujita、Ryohei Yamaguchi

  DOI：10.1021/jo301553v

  日期：2012.10.19

  A simple and convenient CuI/2-pyridonate catalytic system for the oxidative amidation of aldehydes with secondary amines has been developed. With this system, a variety of useful arylamides have been synthesized in moderate to good yields in the presence of small amount of copper catalyst and the pyridonate ligand, generating only water as a coproduct. Synthesis of cinnamamides was also achieved by

  开发了一种简单方便的CuI / 2-吡啶酮催化体系，用于醛与仲胺的氧化酰胺化反应。使用该系统，在少量铜催化剂和吡啶酸酯配体的存在下，已以中等至良好的产率合成了多种有用的芳基酰胺，仅产生水作为副产物。肉桂酰胺与仲胺的反应还可以中等产率合成肉桂酰胺。空气已成功地用作该催化系统中的绿色氧化剂，从而实现了安全，原子效率高的酰胺合成系统。
• Fused imidazopyridine derivatives as antihyperlipidemic agents
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US06235731B1

  公开（公告）日：2001-05-22

  A novel compound of the formula: wherein ring Q is an optionally substituted pyridine ring; One of R0, R1 and R2 is —Y0—Z0, and the other tow groups are a hydrogen, a halogen, an optionally substituted hydroxy group, a hydrocarbon group that may be an optionally substituted hydrocarbon group or an acyl group; Y0 is a bond or an optionally substituted bivalent hydrocarbon group; Z0 is a basic group which may be bonded via oxygen, nitrogen, —CO—, —CS—, —SO2N(R3)— (where R3 is hydrogen or an optionally substituted hydrocarbon group), or S(O)n (wherein n is to 0, 1 or 2); ......... is a single bond or a double bond, or a salt thereof, which has an excellent LDL receptor up-regulating, blood-lipids lowering, blood-sugar lowering and diabetic complication-ameliorating activity.

  其中环Q是一个可选择取代的吡啶环； R0、R1和R2中的一个是—Y0—Z0，另外两个基团是氢、卤素、可选择取代的羟基、可能是可选择取代的碳氢基团或酰基； Y0是一个键或一个可选择取代的二价碳氢基团； Z0是一种碱性基团，可以通过氧、氮、—CO—、—CS—、—SO2N(R3)—（其中R3是氢或可选择取代的碳氢基团）或S(O)n（其中n为0、1或2）与之键合； .........是一种单键或双键，或其盐，具有出色的LDL受体上调、降低血脂、降低血糖和改善糖尿病并发症的活性。
• GPR52 Antagonist Reduces Huntingtin Levels and Ameliorates Huntington’s Disease-Related Phenotypes
  作者：Congcong Wang、Yu-Fang Zhang、Shimeng Guo、Quan Zhao、Yanping Zeng、Zhicheng Xie、Xin Xie、Boxun Lu、Youhong Hu

  DOI：10.1021/acs.jmedchem.0c01133

  日期：2021.1.28

  studies showed that Comp-43 reduces mHTT levels by targeting GPR52 and promotes survival of mouse primary striatal neurons. Moreover, in vivo study showed that Comp-43 not only reduces mHTT levels but also rescues HD-related phenotypes in HdhQ140 mice. Taken together, our study confirms that inhibition of GPR52 is a promising strategy for HD therapy, and the GPR52 antagonist Comp-43 might serve as a lead

  GPR52是一种孤儿G蛋白偶联受体（GPCR），最近被认为是亨廷顿氏病（HD）（一种无法治愈的单基因神经退行性疾病）的潜在药物靶标。在这项研究中，我们发现GPR52的纹状体敲低可降低成年HdhQ140小鼠的mHTT水平，从而将GPR52确认为HD靶标。此外，通过结构-活性关系（SAR）研究，我们发现了一种高效且特异的GPR52拮抗剂Comp- 43，IC 50值为0.63μM 。进一步的研究表明，Comp- 43通过靶向GPR52降低mHTT水平，并促进了小鼠原代纹状体神经元的存活。此外，体内研究表明Comp- 43不仅降低了mHTT水平，而且还挽救了HdhQ140小鼠的HD相关表型。两者合计，我们的研究证实，抑制GPR52是HD治疗的一种有前途的策略，而GPR52拮抗剂Comp- 43可能充当进一步研究的先导化合物。
• Catalytic N‐Acylation of Cyclic Amines by Arylglyoxylic Acids via Radical‐Radical Cross‐Coupling
  作者：Ajijur Rahaman、Anupam Kumar Singh、Aniket Gupta、Sukalyan Bhadra

  DOI：10.1002/ejoc.202100381

  日期：2021.4.22

  A unique copper‐based catalyst system allows for the N‐acylation of cyclic amines by arylglyoxylic acids via radical‐radical cross‐coupling strategy. As evidenced by EPR, UV‐Vis, and mass spectrometric analysis, the amide linkage formation proceeds through a Cu(I)/Cu(II) catalytic cycle involving a twofold SET process.

  独特的铜基催化剂体系可通过自由基-自由基交叉偶联策略使芳基乙醛酸对环胺进行N酰化。正如EPR，UV-Vis和质谱分析所证明的那样，酰胺键的形成过程通过涉及双重SET过程的Cu（I）/ Cu（II）催化循环进行。