2-(4-methylphenyl)-N-(2-phenylpropan-2-yl)benzamide | 249764-83-8

• 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-(4-methylphenyl)-N-(2-phenylpropan-2-yl)benzamide
• CAS: 249764-83-8
• 化学式: C₂₃H₂₃NO
• 分子量: 329.442
• InChiKey: BJMCZOUFBVNNBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(4-methylphenyl)-N-(2-phenylpropan-2-yl)benzamide 在 三氟乙酸 作用下， 以 乙醚 为溶剂， 反应 4.0h， 生成 替米沙坦杂质27
  参考文献：
  名称：

  N-Cumyl Benzamide, Sulfonamide, and Aryl O-Carbamate Directed Metalation Groups. Mild Hydrolytic Lability for Facile Manipulation of Directed Ortho Metalation Derived Aromatics

  摘要：

  [GRAPHICS]N-Cumyl benzamide (2), sulfonamide (8), and O-carbamate (11) compounds undergo directed ortho metalation under standard conditions to give, after quench with a variety of electrophiles, the substituted products 3, 9, and 12, respectively. Regiospecific and convenient approaches to phthalimides (7), 1,2-benzisothiazole 1,1-dioxides (10b), and ortho-substituted phenols (13a) and salicylamides (13b) are thereby established. The mild deprotection protocol for these new cumyl directed metalation groups (DMGs) suggests that they will supersede previous corresponding groups for synthetic anionic aromatic chemistry.

  DOI：

  10.1021/ol990846b
• 作为产物：
  描述：

  2-苯基-2-丙醇 在 四(三苯基膦)钯 lithium aluminium tetrahydride 、 四甲基乙二胺 、 仲丁基锂 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 乙醚 为溶剂， 反应 20.0h， 生成 2-(4-methylphenyl)-N-(2-phenylpropan-2-yl)benzamide
  参考文献：
  名称：

  N-Cumyl Benzamide, Sulfonamide, and Aryl O-Carbamate Directed Metalation Groups. Mild Hydrolytic Lability for Facile Manipulation of Directed Ortho Metalation Derived Aromatics

  摘要：

  [GRAPHICS]N-Cumyl benzamide (2), sulfonamide (8), and O-carbamate (11) compounds undergo directed ortho metalation under standard conditions to give, after quench with a variety of electrophiles, the substituted products 3, 9, and 12, respectively. Regiospecific and convenient approaches to phthalimides (7), 1,2-benzisothiazole 1,1-dioxides (10b), and ortho-substituted phenols (13a) and salicylamides (13b) are thereby established. The mild deprotection protocol for these new cumyl directed metalation groups (DMGs) suggests that they will supersede previous corresponding groups for synthetic anionic aromatic chemistry.

  DOI：

  10.1021/ol990846b

文献信息

• <i>N</i>-Cumyl Benzamide, Sulfonamide, and Aryl <i>O</i>-Carbamate Directed Metalation Groups. Mild Hydrolytic Lability for Facile Manipulation of Directed Ortho Metalation Derived Aromatics
  作者：Costa Metallinos、Sven Nerdinger、Victor Snieckus

  DOI：10.1021/ol990846b

  日期：1999.10.1

  [GRAPHICS]N-Cumyl benzamide (2), sulfonamide (8), and O-carbamate (11) compounds undergo directed ortho metalation under standard conditions to give, after quench with a variety of electrophiles, the substituted products 3, 9, and 12, respectively. Regiospecific and convenient approaches to phthalimides (7), 1,2-benzisothiazole 1,1-dioxides (10b), and ortho-substituted phenols (13a) and salicylamides (13b) are thereby established. The mild deprotection protocol for these new cumyl directed metalation groups (DMGs) suggests that they will supersede previous corresponding groups for synthetic anionic aromatic chemistry.