1-(4'-chlorobenzoyl)-2-hydroxy-3,3-dimethylindoline | 51459-50-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-(4'-chlorobenzoyl)-2-hydroxy-3,3-dimethylindoline
• 英文别名: 1H-Indol-2-ol, 1-(4-chlorobenzoyl)-2,3-dihydro-3,3-dimethyl-；(4-chlorophenyl)-(2-hydroxy-3,3-dimethyl-2H-indol-1-yl)methanone
• CAS: 51459-50-8
• 化学式: C₁₇H₁₆ClNO₂
• 分子量: 301.773
• InChiKey: BEAZUXUWZQUOGU-UHFFFAOYSA-N

物化性质

• 沸点：
  464.7±45.0 °C(Predicted)
• 密度：
  1.289±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4'-chlorobenzoyl)-2-hydroxy-3,3-dimethylindoline 以72%的产率得到
  参考文献：
  名称：

  Kitamura Takeo, Harano Kazunobu, Hisano Takuzo, Chem. and Pharm. Bull., 40 (1992) N 9, S 2255-2261

  摘要：

  DOI：
• 作为产物：
  描述：

  3,3-dimethylindolenine 在 水 作用下， 以 苯 为溶剂， 生成 1-(4'-chlorobenzoyl)-2-hydroxy-3,3-dimethylindoline
  参考文献：
  名称：

  芳环之间的面对面相互作用在与苯形成1-苯甲酰基-2-羟基二氢吲哚衍生物的包合物中的作用。X射线晶体与PM6相互作用的分析

  摘要：

  （4-硝基苯基和4-氯苯基）（2-羟基-3,3-二甲基吲哚-1-基）甲酮（4a，b）是苯客人的包合物主体。对4a和4b与苯的夹杂物进行X射线晶体分析表明，“边对面相互作用”在与苯形成夹杂物以及主体与主体之间的相互作用中起着重要作用。发现PM6分子轨道计算可重现分子内和分子间边对面相互作用的特征结构特征。

  DOI：

  10.1016/j.tet.2011.07.021

文献信息

• Coupling Reaction of 2-Hydroxyindoline with Arenes by BF3Et2O. A Convenient Synthetic Method of Isolable Diastereomeric Atropisomers.
  作者：Takeo KITAMURA、Kazunobu HARANO、Takuzo HISANO

  DOI：10.1248/cpb.40.2255

  日期：——

  A simple method for synthesis of 2-aryl-substituted 3, 3-dimethylindoline derivatives was established by the reaction of 1-acyl-2-hydroxy-3, 3-dimethylindoline with electron-rich arenes in the presence of boron trifluoride-diethly ether in dioxane. In the reaction with β-naphthol, a pair of isolable diastereomeric atropisomers was isolated. The conformations of both atropisomers were determined by single crystal X-ray analyses. The substitution reaction behavior toward various arenes was accounted for in terms of frontier molecular orbital (FMO) theory.

  1-acyl-2-hydroxy-3, 3-dimethylindoline 与富电子烯烃在三氟化硼-二乙醚存在下于二噁烷中反应，建立了合成 2-芳基取代的 3, 3-二甲基吲哚啉衍生物的简单方法。在与β-萘酚的反应中，分离出了一对可分离的非对映异构体。通过单晶 X 射线分析确定了这两种异构体的构象。根据前沿分子轨道（FMO）理论解释了对各种炔烃的取代反应行为。
• Conformation of aromatic rings in isolable atropisomers of 2-arylindoline derivatives and kinetic evidences for π–π interaction
  作者：Masashi Eto、Koki Yamaguchi、Itaru Shinohara、Fumikazu Ito、Yasuyuki Yoshitake、Kazunobu Harano

  DOI：10.1016/j.tet.2009.11.102

  日期：2010.1

  constants [K=anti/syn] of a pair of atropisomers due to restricted rotation about Csp3–Csp2 bond for [2-(2-hydroxynaphthalen-1-yl)-3,3-dimethylindolin-1-yl](4-substituted phenyl)methanone were determined in some solvents. The presence of the effective π–π interaction was demonstrated by the correlation between the equilibrium constants (K) and the substituent effect of the phenyl groups (σp), suggesting that

  由于[2-（2-（2-羟基萘-1-基）-3,3-二甲基吲哚-1-基]围绕Csp 3 -Csp 2键的旋转受限制而导致的一对阻转异构体的平衡常数[ K = anti / syn ]在某些溶剂中测定了（4-取代的苯基）甲酮。有效的π-π相互作用的存在通过平衡常数（K）和苯基的取代基效应（σp）之间的相关性证明，表明“中性型”相互作用是有效的。
• Atropisomers of 1-(Acyl or Aroyl)-2-naphthylindolines. Isolation, X-Ray Crystal Structure and Conformational Analysis
  作者：Fumikazu Ito、Tetsuya Moriguchi、Yasuyuki Yoshitake、Masashi Eto、Shoji Yahara、Kazunobu Harano

  DOI：10.1248/cpb.51.688

  日期：——

  A series of pairs of stable diastereomeric atropisomers caused by restricted rotation around the Csp3–Csp2 bond of [2-(2-hydroxynaphthalen-1-yl)-3,3-dimethyl-2,3-dihydroindol-1-yl]-(3- or 4-substituted phenyl)-methanone or [2-(2-hydroxynaphthalen-1-yl)-3,3-dimethyl-2,3-dihydroindol-1-yl]-1-alkanone were isolated. The conformational analyses of the atropisomers were performed based on the X-ray crystallographic and 1H-NMR spectral data. It became clear that rotation about the C2–naphthyl bond is restricted at room temperature, whereas the >NCO–Ar bond rotates freely.

  分离出一系列稳定的非对映异构体对旋光异构体，它们是由[2-(2-羟基萘-1-基)-3,3-二甲基-2,3-二氢吲哚-1-基]-(3-或4-取代苯基)-甲酮或[2-(2-羟基萘-1-基)-3,3-二甲基-2,3-二氢吲哚-1-基]-1-烷酮的Csp3-Csp2键的受限旋转引起的。根据X射线晶体学和1H-NMR光谱数据对旋光异构体进行了构象分析。结果表明，室温下C2-萘基键的旋转受到限制，而>NCO-Ar键可以自由旋转。
• Role of 2-Naphthyl Ether Intermediate in Formation of Isolable Atropisomers Derived from the Coupling Reaction of (2-Hydroxy-3,3-dimethylindolin-1-yl)(substituted Phenyl)methanones with 2-Naphthol
  作者：Kazunobu Harano、Masashi Eto、Fumikazu Ito、Hidetoshi Sato、Itaru Shinohara、Koki Yamaguchi、Yasuyuki Yoshitake

  DOI：10.3987/com-09-11644

  日期：——

  The formation pathway of the atropisomers derived from the reaction of (2-hydroxy-3,3-dimethylindolin-1-yl)(4-substituted phenyl)methanones with 2-naphthol in the presence of BF(3)center dot Et(2)O was discussed on the basis of the isolation of the 2-naphthyl ether intermediate whose structure was determined by single crystal X-ray analysis, The results indicate that the coupling reaction proceeds through stepwise mechanism, i.e., the ether intermediate formation followed by Fries-type rearrangement.
• Watanabe, Akiko; Yamaguchi, Koki; Ito, Fumikazu, Heterocycles, 2007, vol. 71, # 2, p. 343 - 359
  作者：Watanabe, Akiko、Yamaguchi, Koki、Ito, Fumikazu、Yoshitake, Yasuyuki、Harano, Kazunobu

  DOI：——

  日期：——