1-[3,3-dimethyl-2-(2-methylnaphthalen-1-yl)indolin-1-yl]ethanone | 1567839-31-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-[3,3-dimethyl-2-(2-methylnaphthalen-1-yl)indolin-1-yl]ethanone
• 英文别名: 1-[3,3-dimethyl-2-(2-methylnaphthalen-1-yl)-2H-indol-1-yl]ethanone
• CAS: 1567839-31-9
• 化学式: C₂₃H₂₃NO
• 分子量: 329.442
• InChiKey: JNOUBXLVGUOWKP-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：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3,3-dimethyl-2-(2-methylnaphthalen-1-yl)indoline 、 乙酸酐 以 苯 为溶剂， 反应 16.0h， 以78%的产率得到1-[3,3-dimethyl-2-(2-methylnaphthalen-1-yl)indolin-1-yl]ethanone
  参考文献：
  名称：

  Isolable atropisomers of 2-aryl indoline derivatives: determination of rotational barrier by density functional theory approach

  摘要：

  The rotational process of 2-aryl ring in 1-acyl-2-aryl-3,3-dimethylindolines was determined by density functional theory (DFT) at B3LYP/6-31G(d) level. The calculated barrier height for the rotational process of 12-(2-hydroxynaphthalen-1-y1)-3,3-dimethylindolin-1-yllphenylmethanone (1) was ca. 30 kcal/mol, comparable to the previously reported experimental values of 26-28 kcal/mol for the corresponding derivatives. The Hartree-Fock (HF) calculation overestimated the barrier. The DFT-calculated rotational barrier height provided valuable information for knowing whether the conformers were isolable or not The transition structure analyses showed that the presence of 2,6-substituents on the aryl ring is essential for the isolation of the conformers at room temperature. Based on the DFT-calculated geometries, the rotational process and the intramolecular weak interactions in the restricted rotation were analyzed. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.01.031

文献信息

• Isolable atropisomers of 2-aryl indoline derivatives: determination of rotational barrier by density functional theory approach
  作者：Masashi Eto、Koki Yamaguchi、Akiko Watanabe、Kazunobu Harano

  DOI：10.1016/j.tet.2014.01.031

  日期：2014.3

  The rotational process of 2-aryl ring in 1-acyl-2-aryl-3,3-dimethylindolines was determined by density functional theory (DFT) at B3LYP/6-31G(d) level. The calculated barrier height for the rotational process of 12-(2-hydroxynaphthalen-1-y1)-3,3-dimethylindolin-1-yllphenylmethanone (1) was ca. 30 kcal/mol, comparable to the previously reported experimental values of 26-28 kcal/mol for the corresponding derivatives. The Hartree-Fock (HF) calculation overestimated the barrier. The DFT-calculated rotational barrier height provided valuable information for knowing whether the conformers were isolable or not The transition structure analyses showed that the presence of 2,6-substituents on the aryl ring is essential for the isolation of the conformers at room temperature. Based on the DFT-calculated geometries, the rotational process and the intramolecular weak interactions in the restricted rotation were analyzed. (C) 2014 Elsevier Ltd. All rights reserved.