bis[4-(piperidin-1-yl)phenyl]methanone | 123360-76-9

• 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: bis[4-(piperidin-1-yl)phenyl]methanone
• 英文别名: 4,4'-bis(piperidino)benzophenone；4,4'-dipiperidinobenzophenone；bis(4-piperidin-1-ylphenyl)methanone
• CAS: 123360-76-9
• 化学式: C₂₃H₂₈N₂O
• 分子量: 348.488
• InChiKey: BKYIAKBZZUBSOS-UHFFFAOYSA-N

物化性质

• 熔点：
  152 °C
• 沸点：
  542.6±35.0 °C(Predicted)
• 密度：
  1.116±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙炔钠 、 bis[4-(piperidin-1-yl)phenyl]methanone 在 18-冠醚-6 作用下， 以 四氢呋喃 、 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 168.0h， 生成 1,1-bis(4-(piperidin-1-yl)phenyl)prop-2-yn-1-ol
  参考文献：
  名称：

  Convenient synthesis of diarylpropargyl alcohols

  摘要：

  Reaction between benzophenones and sodium acetylide in THF in the presence of 18-crown-6 gives the corresponding diarylpropargyl alcohols.

  DOI：

  10.1016/j.mencom.2011.11.016
• 作为产物：
  描述：

  哌啶 、 4,4'-二氯二苯甲酮 在 环丁砜 作用下， 反应 24.0h， 以52%的产率得到bis[4-(piperidin-1-yl)phenyl]methanone
  参考文献：
  名称：

  Beach, Steven F.; Hepworth, John D.; Jones, Peter, Journal of the Chemical Society. Perkin transactions II, 1989, p. 1087 - 1090

  摘要：

  DOI：

文献信息

• Ligands for monoamine receptors and transporters, and methods of use thereof
  申请人：——

  公开号：US20030050309A1

  公开（公告）日：2003-03-13

  One aspect of the present invention relates to heterocyclic compounds. A second aspect of the present invention relates to the use of the heterocyclic compounds as ligands for various mammalian cellular receptors, including dopamine, serotonin, or norepinephrine transporters. The compounds of the present invention will find use in the treatment of numerous ailments, conditions and diseases which afflict mammals, including but not limited to addiction, anxiety, depression, sexual dysfunction, hypertension, migraine, Alzheimer's disease, obesity, emesis, psychosis, schizophrenia, Parkinson's disease, inflammatory pain, neuropathic pain, Lesche-Nyhane disease, Wilson's disease, and Tourette's syndrome. An additional aspect of the present invention relates to the synthesis of combinatorial libraries of the heterocyclic compounds, and the screening of those libraries for biological activity, e.g., in assays based on dopamine transporters.

  本发明的一个方面涉及杂环化合物。本发明的第二个方面涉及将这些杂环化合物用作各种哺乳动物细胞受体的配体，包括多巴胺、5-羟色胺或去甲肾上腺素转运体。本发明的化合物将用于治疗许多困扰哺乳动物的疾病、症状和疾病，包括但不限于成瘾、焦虑、抑郁、性功能障碍、高血压、偏头痛、阿尔茨海默病、肥胖、呕吐、精神病、精神分裂症、帕金森病、炎症性疼痛、神经病性疼痛、Lesche-Nyhane病、威尔逊病和抽动症。本发明的另一个方面涉及合成这些杂环化合物的组合式库以及对这些库进行生物活性筛选，例如在基于多巴胺转运体的测定中。
• Method of treating addiction or dependence using a ligand for a monoamine receptor or transporter
  申请人：Aquila M. Brian

  公开号：US20050080078A1

  公开（公告）日：2005-04-14

  One aspect of the present invention relates to a method of treating of drug addiction or drug dependence in a mammal, comprising the step of administering to a mammal in need thereof a therapuetically effective amount of a heterocyclic compound, e.g., a 3-substituted piperidine. In a preferred embodiment, the method of the present invention treats cocaine addiction or methamphetamine addiction.

  本发明的一个方面涉及一种治疗哺乳动物药物成瘾或药物依赖的方法，包括向需要的哺乳动物施用治疗有效量的杂环化合物的步骤，例如，3-取代哌啶。在一个优选实施例中，本发明的方法治疗可卡因成瘾或甲基苯丙胺成瘾。
• Insights into the General and Efficient Cross McMurry Reactions between Ketones
  作者：Xin-Fang Duan、Jing Zeng、Jia-Wei Lü、Zhan-Bin Zhang

  DOI：10.1021/jo061644d

  日期：2006.12.1

  The selective cross McMurry couplings of diaryl or aryl ketones with various substituted ketones were achieved in 53−94% isolated yields. It is believed that the strong affinity of the substituents to the low-valent titanium surface plays an important role in regards to moderating selectivity. Through the introduction of such substituents followed by their removal post McMurry coupling, structurally

  二芳基或芳基酮与各种取代酮的选择性交叉McMurry偶联以53-94％的分离产率实现。据信，取代基对低价钛表面的强亲和力在缓和选择性方面起着重要作用。通过引入此类取代基，然后在McMurry偶联后将其除去，可以有效地交叉偶联结构相似的酮。
• An Environmentally Friendly Synthesis of Michler’s Ketone Analogues in Water
  作者：Valerii Shirinian、Alexey Shimkin、Dmitry Lonshakov、Artur Mailyan、Andrey Lvov、Michail Krayushkin

  DOI：10.1055/s-0031-1289623

  日期：2012.2

  An environmentally friendly method for the synthesis of a series of novel, unsymmetrical Michler’s ketone analogues, [4-(dialkylamino)phenyl](aryl)methanones, via nucleophilic aromatic substitution of (fluorophenyl)(aryl)methanones with various amines in water­ is described. The reaction products are formed in high yields and additional purification is not required. The aqueous solvent and unreacted

  描述了一种环境友好的 方法，该方法可通过在水中用多种胺类进行亲核芳香取代，将一系列新的，不对称的米歇尔酮类似物[4-（二烷基氨基）苯基]（芳基）亚甲基合成。反应产物以高收率形成，不需要额外的纯化。水性溶剂和未反应的胺可以再循环。 米歇尔酮-亲核取代-环保-仲胺-水
• Solid-state Structures of N-Substituted Michler’s Ketones and Their Relation to Solvatochromism
  作者：Stefan Spange、Mohamed El-Sayed、Hardy Müller、Gerd Rheinwald、Heinrich Lang、Wolfgang Poppitz

  DOI：10.1002/1099-0690(200212)2002:24<4159::aid-ejoc4159>3.0.co;2-h

  日期：2002.12

  found to be mainly the dipolarity/polarizability (π*) and hydrogen bond acidity (α) of the solvent that contribute to the bathochromic UV/Vis band shift. As strongly basic sites are present as substituents at the peripheries of the molecules, protonation takes place at the secondary nitrogen atom of, for example, MK(pipaz)2 (2d) in strongly hydrogen bond-donating (HBD) solvents. This specific type of substitution

  N-取代的米氏酮的溶剂化变色 (νmax) - 包括 4'-[双(2-乙酰氧基乙基)氨基]-4-(二甲氨基)二苯甲酮 [MK(OAc)2, 1a], 4,4'-双(二乙氨基) )二苯甲酮 [MK(NEt2)2, 1e], 4,4'-双(4-乙氧基羰基哌嗪基)二苯甲酮 [MK(pipOEt)2, 2a], 4,4'-双(哌啶基)二苯甲酮 [MK(pip)2 , 2b], 4,4'-双(吗啉)二苯甲酮 [MK(mor)2, 2c], 4,4'-双(哌嗪基)二苯甲酮 [MK(pipaz)2, 2d], 4,4'-bis [4-(2-羟乙基)哌嗪基]二苯甲酮 [MK(pipazOH)2, 2e] 和 1,4-双(4-苯甲酰基苯基)哌嗪 (BBP, 3) - 已在 298 K 下在各种溶剂中进行了广泛研究偶极和氢键能力。根据 Kamlet-Taft 线性溶剂化能 (LSE) 关系分析了溶剂化变色特性