2-methyl-2-phenylpentanamide | 100368-87-4

• 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: 2-methyl-2-phenylpentanamide
• 英文别名: 2-methyl-2-phenyl-valeric acid amide；2-Methyl-2-phenyl-valeriansaeure-amid
• CAS: 100368-87-4
• 化学式: C₁₂H₁₇NO
• 分子量: 191.273
• InChiKey: ICVQRZLAEBUECC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  α-甲基苯腈 在 palladium on activated charcoal 正丁基锂 、 水 、 氢气 、 二异丙胺 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 为溶剂， 反应 49.5h， 生成 2-methyl-2-phenylpentanamide
  参考文献：
  名称：

  Platinum-Catalyzed Selective Hydration of Hindered Nitriles and Nitriles with Acid- or Base-Sensitive Groups

  摘要：

  Hindered tertiary nitriles can be hydrolyzed under neutral and mild conditions to the corresponding amides using platinum(II) catalysts with dimethylphosphine oxide or other secondary phosphine oxides (SPOs, phosphinous acids) as ligands. We have found that this procedure also works well for nitriles with acid- or base-sensitive groups, which is unprecedented in terms of yield and selectivity. The catalyst loading can be as low as 0.5 mol %. Amides are isolated as the only product in high yield, and no further hydrolysis to the corresponding acids takes place. Reactions are carried out at 80 degreesC but take place even at room temperature. When enantiopure secondary phosphine oxide ligands are used in the hydrolysis of racemic nitriles, no kinetic resolution is observed, presumably due to racemization of the ligand during the reaction.

  DOI：

  10.1021/jo035487j

文献信息

• [EN] BENZOLACTAM COMPOUNDS AS PROTEIN KINASE INHIBITORS<br/>[FR] COMPOSÉS BENZOLACTAMES UTILISÉS EN TANT QU'INHIBITEURS DE PROTÉINE KINASE
  申请人：OTSUKA PHARMA CO LTD

  公开号：WO2017068412A1

  公开（公告）日：2017-04-27

  The invention provides a compound of formula (0): or a pharmaceutically acceptable salt, N-oxide or tautomer thereof. The compounds are inhibitors of ERK 1/2 kinases and will be useful in the treatment of ERKl/2-mediated conditions. The compounds are therefore useful in therapy, in particular in the treatment of cancer.

  该发明提供了一个化合物，其化学式为(0)：或其药学上可接受的盐、N-氧化物或互变异构体。这些化合物是ERK 1/2激酶的抑制剂，并将在治疗ERKl/2介导的疾病中发挥作用。因此，这些化合物在治疗中特别是在癌症治疗中是有用的。
• Levy; Tabart, Bulletin de la Societe Chimique de France, 1931, vol. <4> 49, p. 1782,1786
  作者：Levy、Tabart

  DOI：——

  日期：——
• BENZOLACTAM COMPOUNDS AS PROTEIN KINASE INHIBITORS
  申请人：Otsuka Pharmaceutical Co., Ltd.

  公开号：EP3365334A1

  公开（公告）日：2018-08-29
• US9006433B2
  申请人：——

  公开号：US9006433B2

  公开（公告）日：2015-04-14
• Platinum-Catalyzed Selective Hydration of Hindered Nitriles and Nitriles with Acid- or Base-Sensitive Groups
  作者：Xiao-bin Jiang、Adriaan J. Minnaard、Ben L. Feringa、Johannes G. de Vries

  DOI：10.1021/jo035487j

  日期：2004.4.1

  Hindered tertiary nitriles can be hydrolyzed under neutral and mild conditions to the corresponding amides using platinum(II) catalysts with dimethylphosphine oxide or other secondary phosphine oxides (SPOs, phosphinous acids) as ligands. We have found that this procedure also works well for nitriles with acid- or base-sensitive groups, which is unprecedented in terms of yield and selectivity. The catalyst loading can be as low as 0.5 mol %. Amides are isolated as the only product in high yield, and no further hydrolysis to the corresponding acids takes place. Reactions are carried out at 80 degreesC but take place even at room temperature. When enantiopure secondary phosphine oxide ligands are used in the hydrolysis of racemic nitriles, no kinetic resolution is observed, presumably due to racemization of the ligand during the reaction.