5-甲基-2-(嘧啶-2-基)苯甲腈 | 1373917-20-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 5-甲基-2-(嘧啶-2-基)苯甲腈
• 英文名称: 5-methyl-2-pyrimidin-2-ylbenzonitrile
• 英文别名: 4-methyl-2-(pyrimidin-2-yl)benzonitrile；5-Methyl-2-(pyrimidin-2-yl)benzonitrile
• CAS: 1373917-20-4
• 化学式: C₁₂H₉N₃
• 分子量: 195.224
• InChiKey: ACBRZBTVCIFPCJ-UHFFFAOYSA-N

物化性质

• 沸点：
  296.4±40.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  49.6
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  5-甲基-2-(嘧啶-2-基)苯甲腈 在 2,6-二甲基吡啶 、 盐酸 、 三甲基乙酰氯 、 1-丙基磷酸酐 作用下， 以 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 50.0h， 生成 MK-6096
  参考文献：
  名称：

  Unusual Pyrimidine Participation: Efficient Stereoselective Synthesis of Potent Dual Orexin Receptor Antagonist MK-6096

  摘要：

  An asymmetric synthesis of dual orexin receptor antagonist MK-6096 (1) is described. Key steps for the trans-2,5-disubstituted piperidinyl ether fragment include a biocatalytic transamination, a trans-selective Mukaiyama aldol, and a regioselective pyridyl SNAr process. The pyrimidyl benzoic acid was synthesized via a Negishi coupling and a nitrile hydrolysis. Coupling of the two fragments via a catalytic T3P-mediated amidation completed the synthesis. Unusual behaviors in the hydrolysis of pyrimidyl benzonitrile and the amide coupling of the pyrimidyl benzoic acid are also described.

  DOI：

  10.1021/ol5028249
• 作为产物：
  描述：

  2-溴-5-甲基苯腈 在 lithium chloro-isopropyl-magnesium chloride 、 三丁基膦 、 正丁基氯化镁 、 palladium diacetate 作用下， 以 四氢呋喃 为溶剂， 反应 21.0h， 生成 5-甲基-2-(嘧啶-2-基)苯甲腈
  参考文献：
  名称：

  Unusual Pyrimidine Participation: Efficient Stereoselective Synthesis of Potent Dual Orexin Receptor Antagonist MK-6096

  摘要：

  An asymmetric synthesis of dual orexin receptor antagonist MK-6096 (1) is described. Key steps for the trans-2,5-disubstituted piperidinyl ether fragment include a biocatalytic transamination, a trans-selective Mukaiyama aldol, and a regioselective pyridyl SNAr process. The pyrimidyl benzoic acid was synthesized via a Negishi coupling and a nitrile hydrolysis. Coupling of the two fragments via a catalytic T3P-mediated amidation completed the synthesis. Unusual behaviors in the hydrolysis of pyrimidyl benzonitrile and the amide coupling of the pyrimidyl benzoic acid are also described.

  DOI：

  10.1021/ol5028249

文献信息

• [EN] PROCESS FOR THE PREPARATION OF AN OREXIN RECEPTOR ANTAGONIST<br/>[FR] PROCÉDÉ DE PRÉPARATION D'UN ANTAGONISTE DU RÉCEPTEUR DE L'OREXINE
  申请人：MERCK SHARP & DOHME

  公开号：WO2012058129A1

  公开（公告）日：2012-05-03

  The present invention is directed to processes for preparing a pyridyl piperidine compound which is an antagonist of orexin receptors, and which is useful in the treatment or prevention of neurological and psychiatric disorders and diseases in which orexin receptors are involved.

  本发明涉及制备吡啶基哌啶化合物的方法，该化合物是促进睡眠的受体拮抗剂，可用于治疗或预防涉及促进睡眠的神经和精神障碍和疾病。
• α-Iminonitrile: a new cyanating agent for the palladium catalyzed C–H cyanation of arenes
  作者：Zhen-Bang Chen、Fang-Ling Zhang、Qing Yuan、Hai-Fang Chen、Yong-Ming Zhu、Jing-Kang Shen

  DOI：10.1039/c6ra14512d

  日期：——

  An efficient palladium-catalyzed C–H cyanation reaction of arenes using α-iminonitrile as a new cyanating reagent has been developed.

  一种高效的钯催化芳烃C-H氰化反应已经开发出来，使用α-亚胺腈作为新的氰化试剂。
• Rhodium-Catalyzed Direct C–H Bond Cyanation of Arenes with Isocyanide
  作者：Xiaohu Hong、Hao Wang、Guangyin Qian、Qitao Tan、Bin Xu

  DOI：10.1021/jo500087g

  日期：2014.4.4

  An efficient rhodium-catalyzed regioselective C-H bond cyanation of arenes was developed using tert-butyl isocyanide as the cyanide source. A wide range of (hetero)aryl and cycloalkenyl nitriles could be afforded with high regioselectivity and good functional group tolerance.
• Org. Lett. 2014, 16, 5890-5893
  作者：

  DOI：——

  日期：——
• PROCESS FOR THE PREPARATION OF AN OREXIN RECEPTOR ANTAGONIST
  申请人：Merck Sharp & Dohme Corp.

  公开号：EP2632253B1

  公开（公告）日：2016-04-06