tert-butyl 4-(naphthalen-1-yl)piperazine-1-carboxylate | 206347-34-4

• 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-(naphthalen-1-yl)piperazine-1-carboxylate
• 英文别名: tert-butyl 4-(naphthalene-1-yl)piperazine-1-carboxylate；1-Piperazinecarboxylic acid, 4-(1-naphthalenyl)-, 1,1-dimethylethyl ester；tert-butyl 4-naphthalen-1-ylpiperazine-1-carboxylate
• CAS: 206347-34-4
• 化学式: C₁₉H₂₄N₂O₂
• 分子量: 312.412
• InChiKey: SWSYBZJEUSXCHF-UHFFFAOYSA-N

物化性质

• 沸点：
  458.4±38.0 °C(Predicted)
• 密度：
  1.139±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  32.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-(naphthalen-1-yl)piperazine-1-carboxylate 在 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 13.0h， 生成 N-(4-(4-(naphthalen-1-yl)piperazin-1-yl)butyl)benzamide
  参考文献：
  名称：

  Targeting Dopamine D₃ and Serotonin 5-HT_1A and 5-HT_2A Receptors for Developing Effective Antipsychotics: Synthesis, Biological Characterization, and Behavioral Studies

  摘要：

  Combination of dopamine D-3 antagonism, serotonin 5-HT1A partial agonism, and antagonism at 5-HT2A leads to a novel approach to potent atypical antipsychotics. Exploitation of the original structureactivity relationships resulted in the identification of safe and effective antipsychotics devoid of extrapyramidal symptoms liability, sedation, and catalepsy. The potential atypical antipsychotic 5bb was selected for further pharmacological investigation. The distribution of c-fos positive cells in the ventral striatum confirmed the atypical antipsychotic profile of 5bb in agreement with behavioral rodent studies. 5bb administered orally demonstrated a biphasic effect on the MK801-induced hyperactivity at dose levels not able to induce sedation, catalepsy, or learning impairment in passive avoidance. In microdialysis studies, 5bb increased the dopamine efflux in the medial prefrontal cortex. Thus, 5bb represents a valuable lead for the development of atypical antipsychotics endowed with a unique pharmacological profile for addressing negative symptoms and cognitive deficits in schizophrenia.

  DOI：

  10.1021/jm501119j
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 palladium diacetate 、 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 溶剂黄146 作用下， 以 1,4-二氧六环 为溶剂， 反应 21.17h， 生成 tert-butyl 4-(naphthalen-1-yl)piperazine-1-carboxylate
  参考文献：
  名称：

  [EN] COMPOUNDS FOR BINDING PROPROTEIN CONVERTASE SUBTILISIN/KEXIN TYPE 9 (PCSK9)
  [FR] COMPOSÉS SE LIANT À LA PROPROTÉINE CONVERTASE SUBTILISINE/KEXINE DE TYPE 9 (PCSK9)

  摘要：

  本公开涉及与PCSK9结合的新化合物、方法和组合物，从而调节PCSK9前蛋白酶酶活性。本公开的化合物包括化合物式（I）。

  公开号：

  WO2017147328A1

文献信息

• Novel Aryl Piperazine Derivatives With Medical Utility
  申请人：Campiani Giuseppe

  公开号：US20090238761A1

  公开（公告）日：2009-09-24

  This invention provides novel aryl piperazine derivatives having medical utility, in particular as modulators of dopamine and serotonin receptors, preferably the D 3 , D 2 -like and 5-HT 2 receptor subtypes, and in particular useful for the treatment of neuropsychiatric disorders incl. schizophrenia.

  这项发明提供了具有医疗效用的新型芳基哌嗪衍生物，特别是作为多巴胺和5-羟色胺受体的调节剂，优选为D3、D2样和5-HT2受体亚型，特别适用于治疗包括精神分裂症在内的神经精神障碍。
• Scope and Utility of CsOH·H₂O in Amination Reactions via Direct Coupling of Aryl Halides and<i>sec</i>-Alicyclic Amines
  作者：Srinivas R. Adapa、Ravi Varala、E. Ramu、M. Mujahid Alam

  DOI：10.1055/s-2004-830853

  日期：——

  Direct coupling of aryl halides with sec-alicyclic amines promoted by CsOH·H2O in DMSO to the corresponding aryl substituted amines, with good to excellent yields, is reported herein. A variety of aryl halides and sec-alicyclic amines with a broad range of electronic diversity and functional groups was studied in this transformation, thus offering general applicability in organic synthesis.

  本文报告了芳基卤化物与仲脂环胺在 DMSO 中 CsOH-H2O 的促进下直接偶联生成相应的芳基取代胺的过程，收率从良好到极佳。在这一转化过程中，研究了多种具有广泛电子多样性和官能团的芳基卤化物和仲脂环胺，从而为有机合成提供了普遍适用性。
• Direct Chan–Lam Amination and Etherification of Aryl BMIDA Reagents
  作者：John M. Halford‐McGuff、Eva M. Israel、Matthew J. West、Julien C. Vantourout、Allan J. B. Watson

  DOI：10.1002/ejoc.202200993

  日期：2022.12.6

  The direct Chan–Lam coupling of arylboronic acid methyliminodiacetic acid esters (ArBMIDA) with amine and alcohol nucleophiles is reported. Limitations of the process are also discussed. We also demonstrate how this method can be used in the chemoselective synthesis of heterocyclic scaffolds by using the unique attributes of the BMIDA protecting group.

  报道了芳基硼酸甲基亚氨基二乙酸酯 (ArBMIDA) 与胺和醇亲核试剂的直接 Chan-Lam 偶联。还讨论了该过程的局限性。我们还展示了如何通过使用 BMIDA 保护基团的独特属性，将此方法用于杂环支架的化学选择性合成。
• Synthesis of arylpiperazines via palladium-catalysed aromatic amination reactions of bromoarenes with N-tert-butoxycarbonylpiperazine
  作者：Frank Kerrigan、Claire Martin、Gerard H. Thomas

  DOI：10.1016/s0040-4039(98)00179-8

  日期：1998.4

  Reaction of a series of bicyclic bromoarenes with N-tert-butoxycarbonylpiperazine (N-Boc-piperazine) under palladium-calalysed coupling conditions followed by routine removal of the Boc group with trifluoroacetic acid in dichloromethane gave the corresponding arylpiperazines in moderate to good yield. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Discovery of imidazole carboxamides as potent and selective CCK1R agonists
  作者：Cheng Zhu、Alexa R. Hansen、Thomas Bateman、Zhesheng Chen、Tom G. Holt、James A. Hubert、Bindhu V. Karanam、Susan J. Lee、Jie Pan、Su Qian、Vijay B.G. Reddy、Marc L. Reitman、Alison M. Strack、Vincent Tong、Drew T. Weingarth、Michael S. Wolff、Doug J. MacNeil、Ann E. Weber、Joseph L. Duffy、Scott D. Edmondson

  DOI：10.1016/j.bmcl.2008.06.057

  日期：2008.8

  High-throughput screening revealed diaryl pyrazole 3 as a selective albeit modest cholecystokinin 1 receptor (CCK1R) agonist. SAR studies led to the discovery and optimization of a novel class of 1,2-diaryl imidazole carboxamides. Compound 44, which was pro. led extensively, showed good in vivo mouse gallbladder emptying (mGBE) and lean mouse overnight food intake (ONFI) reduction activities. (c) 2008 Elsevier Ltd. All rights reserved.