4,6-二氯-2-(1-吡咯烷基)嘧啶 | 154117-91-6

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 4,6-二氯-2-(1-吡咯烷基)嘧啶
• 中文别名: 4,6-二氯-2-(吡咯烷-1-基)嘧啶
• 英文名称: 4,6-dichloro-2-pyrrolidin-1-yl-pyrimidine
• 英文别名: 4,6-Dichloro-2-(pyrrolidin-1-yl)pyrimidine；4,6-dichloro-2-pyrrolidin-1-ylpyrimidine
• CAS: 154117-91-6
• 化学式: C₈H₉Cl₂N₃
• mdl: MFCD09607722
• 分子量: 218.086
• InChiKey: LZHQEVZABXPJNN-UHFFFAOYSA-N

物化性质

• 沸点：
  356.2±45.0 °C(Predicted)
• 密度：
  1.413±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  4,6-二氯-2-(1-吡咯烷基)嘧啶 在 sodium hydroxide 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 11.0h， 生成 4-amino-N-[6-chloro-2-(pyrrolidin-1-yl)pyrimidin-4-yl]benzenesulfonamide
  参考文献：
  名称：

  5-HT6 receptor antagonists: lead optimisation and biological evaluation of N-aryl and N-heteroaryl 4-amino-benzene sulfonamides

  摘要：

  RO-04-6790 (6a) has been identified in a random screen for 5-HT6 receptor antagonists. In a medicinal chemistry optimisation program a series of analogs comprising N-heteroaryl- and N-arylbenzenesulfonamides have been synthesised and investigated for their binding affinity. Compounds with a log D profile indicative of brain penetration have been subjected to in vivo testing for reversal of a scopolamine-induced retention deficit in a passive avoidance paradigm. (C) 2001 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)01209-5
• 作为产物：
  描述：

  四氢吡咯 、 2,4,6-三氯嘧啶 在 水 、 正己烷 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以to give 7.51 g (25.27%) of 4,6-dichloro-2-pyrrolidinopyrimidine, m.p. 95°-98° C.的产率得到4,6-二氯-2-(1-吡咯烷基)嘧啶
  参考文献：
  名称：

  Piperazinyl-bis(alkylamino)pyrimidine derivatives and process for

  摘要：

  本发明揭示了一种中间化合物，其在制备抑制脂质过氧化的物质中非常有用，所述中间化合物选自以下组合：2,4-双[1-金刚烷基]氨基-6-(1-哌嗪基)嘧啶；和4,6-双(1-金刚烷基)氨基-2-(1-哌嗪基)嘧啶；或其药学上可接受的酸盐。

  公开号：

  US05550240A1

文献信息

• Piperazinyl-bis(alkylamino)pyrimidine derivatives and process for
  申请人：Richter Gedeon Vegyeszeti Gyar Rt.

  公开号：US05550240A1

  公开（公告）日：1996-08-27

  An intermediate compound is disclosed that is useful in the preparation of a lipid-peroxidation inhibiting substance and that is selected from the group consisting of: 2,4-bis[1-adamantylamino]-6-(1-piperazinyl)pyrimidine; and 4,6-bis(1-adamantylamino)-2-(1-piperazinyl)pyrimidine; or a pharmaceutically acceptable acid addition salt thereof.

  披露了一种中间化合物，该化合物在制备抑制脂质过氧化的物质时非常有用，该化合物选自以下组：2,4-双[1-金刚烷基氨基]-6-(1-哌嗪基)嘧啶；以及4,6-双(1-金刚烷基氨基)-2-(1-哌嗪基)嘧啶；或其药用可接受的酸加成盐。
• Facile aromatic nucleophilic substitution (S_NAr) reactions in ionic liquids: an electrophile–nucleophile dual activation by [Omim]Br for the reaction
  作者：Xiao Zhang、Guo-ping Lu、Chun Cai

  DOI：10.1039/c6gc01742h

  日期：——

  A facile aromatic nucleophilic substitution reaction (SNAr) in recyclable [Omim]Br under relatively mild conditions has been described. An electrophile-nucleophile dual activation by [Omim]Br is also discovered based on control experiments,...

  已经描述了在相对温和的条件下在可再循环的[Omim] Br中的容易的芳族亲核取代反应（SNAr）。基于对照实验，还发现了[Omim] Br引起的亲电亲核双重激活，...
• Highly Selective Hydrolysis of Chloropyrimidines to Pyrimidones in 12 N Hydrochloric Acid
  作者：Amphlett G. Padilla、Bruce A. Pearlman

  DOI：10.1021/op060093q

  日期：2006.9.1

  using methodological tools developed by Bunnett established that the transition state for hydrolysis of the 6-chloro isomer involves two more molecules of water (each acting as a base) than does the transition state for hydrolysis of the 2-chloro isomer. As the concentration of HCl increases from 3 N to 6 N to 12 N, there are fewer unprotonated water molecules. Thus, the transition state that involves

  描述了无色谱法合成异构纯形式的6-哌嗪基-2,4-双-吡咯烷基基嘧啶。关键步骤是通过以下方法纯化粗制的6-氯-2,4-双-吡咯烷基基嘧啶/ 2-氯-4,6-双-吡咯烷基基嘧啶异构体混合物（通过2,4,6-三氯嘧啶与吡咯烷的反应生成） 2-氯异构体的高选择性酸催化水解为嘧啶酮。在6 N HCl中，2-氯异构体的水解速度是6-氯异构体的350倍，在12 N HCl中的水解速度是1750倍。为了正确看待这些比率，2-氯异构体与胺和醇盐的反应仅比6-氯异构体快约10-17倍。使用Bunnett开发的方法学工具进行的机械研究确定，6-氯异构体水解的过渡态比2-氯异构体水解的过渡态所涉及的水分子多于两个分子（每个都作为碱）。随着HCl浓度从3 N增加到6 N再增加到12 N，未质子化的水分子就会减少。因此，如所观察到的，涉及较多数量的未质子化的水分子（6-氯-2,4-双-吡咯烷基基嘧啶）的过渡态预计将
• NEW COMPOUNDS, PHARMACEUTICAL COMPOSITIONS AND USES THEREOF
  申请人：ROTH Gerald Juergen

  公开号：US20120157425A1

  公开（公告）日：2012-06-21

  The invention relates to new piperidine derivatives of the formula I to their use as medicaments, to methods for their therapeutic use and to pharmaceutical compositions containing them.

  该发明涉及新的哌啶衍生物，其化学式I，用作药物，用于治疗的方法以及含有它们的药物组合物。
• Biologically active eburnamenine derivatives, pharmaceutical
  申请人：Richter Gedeon Vegyeszeti Gyar Rt.

  公开号：US05510345A1

  公开（公告）日：1996-04-23

  The invention relates to novel eburnamenine derivatives of formula (I): ##STR1## wherein R.sup.1 and R.sup.2 as well as R.sup.3 and R.sup.4, independently from each other, stand for hydrogen, C.sub.2-6 alkyl group, C.sub.2-6 alkenyl group; or a C.sub.3-10 alicyclic group involving 1 to 3 rings, and this latter group may be substituted by a C.sub.1-6 alkyl or C.sub.2-6 alkenyl group; or R.sup.1 and R.sup.2 and/or R.sup.3 and R.sup.4, together with the adjacent nitrogen atom and optionally with an additional oxygen or nitrogen atom, form a 4- to 6-membered, saturated or unsaturated cyclic group which may be substituted by a C.sub.1-6 alkyl or C.sub.2-6 alkenyl group; two of X, Y and Z are nitrogen whereas the third of them means a methine group; n is 1 or 2; W means oxygen or two hydrogen atoms; and the wavy line means .alpha.-/.alpha.-, .alpha.-/.beta.- or .beta.-/.alpha.- steric position, as well as their acid addition salts and solvates. The invention further relates to pharmaceutical compositions containing the above compounds as well as a process for preparing the compounds of formula (I). The compounds of formula (I) possess antioxidant effect and therefore, they are useful for inhibiting the peroxidation of lipids occurring in mammals (including human).

  该发明涉及式(I)的新型eburnamenine衍生物：其中R.sup.1和R.sup.2以及R.sup.3和R.sup.4，彼此独立地代表氢、C.sub.2-6烷基、C.sub.2-6烯基；或涉及1至3个环的C.sub.3-10脂环基，该后者可以被C.sub.1-6烷基或C.sub.2-6烯基基团取代；或者R.sup.1和R.sup.2和/或R.sup.3和R.sup.4，与相邻氮原子以及可选地与额外的氧原子或氮原子一起形成一个4到6元的饱和或不饱和环基团，该环基团可以被C.sub.1-6烷基或C.sub.2-6烯基基团取代；X、Y和Z中的两个是氮，第三个是甲基基团；n为1或2；W表示氧或两个氢原子；波浪线表示α-/α-、α-/β-或β-/α-立体位置，以及它们的酸盐和溶剂化合物。该发明还涉及含有上述化合物的药物组合物以及制备式(I)化合物的方法。式(I)化合物具有抗氧化作用，因此它们可用于抑制发生在哺乳动物（包括人类）中的脂质过氧化。