alpha,alpha-二甲基-1-哌啶乙腈 | 2273-41-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: alpha,alpha-二甲基-1-哌啶乙腈
• 中文别名: 2-甲基-2-哌啶-1-基丙腈
• 英文名称: 2-methyl-2-(1-piperidinyl)propanenitrile
• 英文别名: 2-methyl-2-(piperidin-1-yl)propanenitrile；α-piperidino-isobutyronitrile；2-methyl-2-piperidinopropionitrile；2-piperidino-2-cyanopropane；2-Methyl-2-piperidin-1-ylpropanenitrile
• CAS: 2273-41-8
• 化学式: C₉H₁₆N₂
• mdl: MFCD10005351
• 分子量: 152.239
• InChiKey: IGSJLBUPRRXRDY-UHFFFAOYSA-N

物化性质

• 溶解度：
  可溶于丙酮、氯仿

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.888
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  alpha,alpha-二甲基-1-哌啶乙腈 在 bis-triphenylphosphine-palladium(II) chloride 、 四丁基氟化铵 、 碘 、 caesium carbonate 、 magnesium 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 乙醚 、 水 为溶剂， 反应 14.08h， 生成 3-(4-(2-(piperidin-1-yl)propan-2-yl)phenyl)-9H-pyrrolo[2,3-b:5,4-c′]dipyridine-6-carbonitrile
  参考文献：
  名称：

  Mitigation of Acetylcholine Esterase Activity in the 1,7-Diazacarbazole Series of Inhibitors of Checkpoint Kinase 1

  摘要：

  Checkpoint kinase 1 (ChK1) plays a key role in the DNA damage response, facilitating cell-cycle arrest to provide sufficient time for lesion repair. This leads to the hypothesis that inhibition of ChK1 might enhance the effectiveness of DNA-damaging therapies in the treatment of cancer. Lead compound 1 (GNE-783), the prototype of the 1,7-diazacarbazole class of ChK1 inhibitors, was found to be a highly potent inhibitor of acetylcholine esterase (AChE) and unsuitable for development. A campaign of analogue synthesis established SAR delineating ChK1 and AChE activities and allowing identification of new leads with improved profiles. In silico docking using a model of AChE permitted rationalization of the observed SAR. Compounds 19 (GNE-900) and 30 (GNE-145) were identified as selective, orally bioavailable ChK1 inhibitors offering excellent in vitro potency with significantly reduced AChE activity. In combination with gemcitabine, these compounds demonstrate an in vivo pharmacodynamic effect and are efficacious in a mouse p53 mutant xenograft model.

  DOI：

  10.1021/acs.jmedchem.5b00464
• 作为产物：
  描述：

  哌啶 、 N-氰基-N'-甲基乙脒 以 neat (no solvent) 为溶剂， 以93%的产率得到alpha,alpha-二甲基-1-哌啶乙腈
  参考文献：
  名称：

  Transamination of α-amino nitriles

  摘要：

  alpha-Amino nitriles containing a primary amino group undergo transamination with aliphatic and aromatic amines under mild conditions with high yields. A probable reaction mechanism involving intermediate elimination of cyanide ion has been proposed.

  DOI：

  10.1134/s1070428014010047

文献信息

• New nucleophilic rearrangement in the mechanism of the three-component domino cyclisation affording fluoroalkylated (pyrrolo)quinazolines
  作者：Oldřich Paleta、Bohumil Dolenský、Jiří Paleček、Jaroslav Kvíčala

  DOI：10.1016/j.jfluchem.2013.10.017

  日期：2014.1

  steps were verified for the three-component domino cyclisation affording (pyrrolo)quinazolines from 2-(aminomethyl)aniline, a very reactive oxo compound and “usual” oxo compound. The first step was a rapid reaction of very reactive oxo compound (trifluoropyruvate or hexafluoroacetone) with benzylic amino group to form hemiaminal, but not imine; the second step was the reaction of oxo compound with aromatic

  以下机构的步骤进行验证为具有三种成分的多米诺环化，得到（吡咯），从2-（氨基甲基）苯胺，很活泼的氧代化合物和“通常”氧代喹唑啉化合物。第一步是使反应性很强的羰基化合物（三氟丙酮酸或六氟丙酮）与苄基氨基快速反应，形成半胱氨酸，但不能形成亚胺。第二步是使羰基化合物与芳族氨基反应生成亚胺（席夫碱），其烯胺形式处于平衡状态。第三步骤是通过烯胺碳后跟一个新亲核重排以形成四氢周期的半缩醛胺的碳的分子内攻击; 第四步骤是内酰胺环的闭合，如果酯基团是可作为三氟丙酮。
• Novel and Convenient Aldolization of Methyl 3,3,3-Trifluoropyruvate Using Enamines Instead of Ketones
  作者：Oldřich Paleta、Jiří Paleček

  DOI：10.1055/s-2004-815954

  日期：——

  Piperidine enamines derived from acetone, acetophenone, cyclopentanone and cyclohexanone react easily in minutes with methyl 3,3,3-trifluoropyruvate (1) to afford products of the aldol condensation in high yields at room temperature, which is in contrast to the direct aldolization of 1 with the ketones.

  从丙酮、苯乙酮、环戊酮和环己酮中提取的哌啶烯胺与 3,3,3-三氟丙酮酸甲酯（1）很容易在几分钟内发生反应，并在室温下以高产率得到醛醇缩合产物，这与 1 与酮的直接醛化形成鲜明对比。
• COMPOUNDS HAVING ACTIVITY AT THE GLYCINE TRANSPORTER GLYT1 AND USES THEREOF
  申请人：Branch Clive Leslie

  公开号：US20090227629A1

  公开（公告）日：2009-09-10

  The present invention relates to compounds of formula (I), salts or solvates thereof, their use in the manufacture of medicaments for treating neurological and neuropsychiatric disorders, in particular psychoses, dementia or attention deficit disorder. The invention further comprises processes to make these compounds and pharmaceutical formulations thereof. wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and n are as defined in the description.

  本发明涉及化合物(I)的公式，其盐或溶剂，其用于制造治疗神经和神经精神障碍的药物，特别是精神病、痴呆或注意力缺陷障碍的药物。本发明还包括制造这些化合物和药物配方的过程。其中R1、R2、R3、R4、R5、R6和n如描述中所定义。
• Glycine Transport Inhibitors
  申请人：Bradley Daniel Marcus

  公开号：US20080287547A1

  公开（公告）日：2008-11-20

  The present invention relates to compounds of formula (I), or to salts or solvates thereof, their use in the manufacture of medicaments for treating neurological and neuropsychiatric disorders, in particular psychoses, dementia or attention deficit disorder. The invention further comprises processes to make these compounds and pharmaceutical formulations thereof.

  本发明涉及公式（I）的化合物，或其盐或溶剂化物，其用于制造治疗神经和神经精神障碍的药物，特别是精神病、痴呆或注意力缺陷障碍。该发明还包括制备这些化合物和制药配方的过程。
• Glycine transport inhibitors
  申请人：Glaxo Group Limited

  公开号：US07745642B2

  公开（公告）日：2010-06-29

  The present invention relates to compounds of formula (I), or to salts or solvates thereof, their use in the manufacture of medicaments for treating neurological and neuropsychiatric disorders, in particular psychoses, dementia or attention deficit disorder. The invention further comprises processes to make these compounds and pharmaceutical formulations thereof.

  本发明涉及公式（I）的化合物，或其盐或溶剂化物，它们在制造用于治疗神经系统和神经精神障碍的药物中的使用，特别是用于治疗精神病、痴呆或注意力缺陷障碍。该发明还包括制备这些化合物和它们的药物制剂的过程。