1-methyl-1,2,3,4-tetrahydrobenzo[b]azepin-5-one | 1407968-50-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: 1-methyl-1,2,3,4-tetrahydrobenzo[b]azepin-5-one
• 英文别名: 1-Methyl-2,3,4,5-tetrahydro-1-benzazepin-5-ol；1-methyl-2,3,4,5-tetrahydro-1-benzazepin-5-ol
• CAS: 1407968-50-6
• 化学式: C₁₁H₁₅NO
• 分子量: 177.246
• InChiKey: QVBDKOPEJVMJMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-[N-(2-iodophenyl)-N-methylamino]butanol 在 四(三苯基膦)钯 、 草酰氯 、 caesium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 、 甲苯 为溶剂， 反应 0.33h， 生成 1-甲基-1,2,3,4-四氢喹啉-4-酮 、 1-methyl-1,2,3,4-tetrahydrobenzo[b]azepin-5-one 、 1-methyl-1,2,3,4-tetrahydrobenzo[b]azepin-5-one
  参考文献：
  名称：

  Intramolecular Pd(0)-Catalyzed Reactions of (2-Iodoanilino)-aldehydes: A Joint Experimental–Computational Study

  摘要：

  An extensive joint experimental-computational density functional theory (DFT) study has been carried out to gain insight into the factors that control the chemoselectivity (i.e., acylation vs alpha-arylation reaction) of palladium-catalyzed cyclizations of (2-iodoanilino)-aldehydes. To this end, the nature of the tethers joining the aniline nitrogen and the aldehyde moiety, different palladium precatalysts and reaction conditions (base and temperature), as well as different additives (mono- and bidendate ligands) has been explored. The adequate selection of these variables allows for the control of the selectivity of the process. Thus, (2-iodoanilino)-aldehydes generally lead to the formation of nucleophilic addition derived products when Cs2CO3/Et3N is used as base. In contrast, the use of stronger bases like (KOBu)-O-t (in the presence of PhOH) mainly forms alpha-arylation reaction products. The different reaction pathways leading to the experimentally observed reaction products have been studied by means of computational tools.

  DOI：

  10.1021/jo301924e

文献信息

• NAPHTALENE COMPOUNDS TO TREAT ITCH
  申请人：Mitsubishi Tanabe Pharma Corporation

  公开号：EP2727594B1

  公开（公告）日：2017-12-20
• Intramolecular Pd(0)-Catalyzed Reactions of (2-Iodoanilino)-aldehydes: A Joint Experimental–Computational Study
  作者：Daniel Solé、Francesco Mariani、Israel Fernández、Miguel A. Sierra

  DOI：10.1021/jo301924e

  日期：2012.11.16

  An extensive joint experimental-computational density functional theory (DFT) study has been carried out to gain insight into the factors that control the chemoselectivity (i.e., acylation vs alpha-arylation reaction) of palladium-catalyzed cyclizations of (2-iodoanilino)-aldehydes. To this end, the nature of the tethers joining the aniline nitrogen and the aldehyde moiety, different palladium precatalysts and reaction conditions (base and temperature), as well as different additives (mono- and bidendate ligands) has been explored. The adequate selection of these variables allows for the control of the selectivity of the process. Thus, (2-iodoanilino)-aldehydes generally lead to the formation of nucleophilic addition derived products when Cs2CO3/Et3N is used as base. In contrast, the use of stronger bases like (KOBu)-O-t (in the presence of PhOH) mainly forms alpha-arylation reaction products. The different reaction pathways leading to the experimentally observed reaction products have been studied by means of computational tools.