6,6-dimethyl-1,2-diphenyl-1,5,6,7-tetrahydro-4H-indol-4-one | 68638-85-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 6,6-dimethyl-1,2-diphenyl-1,5,6,7-tetrahydro-4H-indol-4-one
• 英文别名: 6,6-dimethyl-1,2-diphenyl-6,7-dihydro-1H-indol-4(5H)-one；6,6-dimethyl-1,2-diphenyl-5,7-dihydroindol-4-one
• CAS: 68638-85-7
• 化学式: C₂₂H₂₁NO
• mdl: MFCD00265990
• 分子量: 315.415
• InChiKey: KQSSMCPKNVMYEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6,6-dimethyl-1,2-diphenyl-1,5,6,7-tetrahydro-4H-indol-4-one 在 吡啶 、 盐酸羟胺 作用下， 以0.6 g的产率得到N-(6,6-dimethyl-1,2-diphenyl-5,7-dihydroindol-4-ylidene)hydroxylamine
  参考文献：
  名称：

  Nagarajan, K.; Talwalker, P. K.; Shah, R. K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1985, vol. 24, p. 98 - 111

  摘要：

  DOI：
• 作为产物：
  描述：

  5,5-二甲基-1,3-环己二酮 在 potassium carbonate 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 生成 6,6-dimethyl-1,2-diphenyl-1,5,6,7-tetrahydro-4H-indol-4-one
  参考文献：
  名称：

  Dagher, C.; Hanna, R.; Terentiev, P. B., Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 645 - 647

  摘要：

  DOI：

文献信息

• Wang resin-supported sulfonic acid-catalyzed multicomponent reaction in water leading to 4-oxo-4,5,6,7-tetrahydroindole derivatives
  作者：Naresh Kumar Reddy Dinne、Ramamohan Mekala、S. Pulla Reddy、Ganesh Yaddanapudi Sesha Siva、Chandrasekhar Kothapalli Bannoath

  DOI：10.1080/00397911.2018.1458240

  日期：2018.7.3

  ABSTRACT A greener approach for the synthesis of 4-oxo-4,5,6,7-tetrahydro indole derivatives has been achieved through Wang-OSO3H-mediated three-component reaction involving dimedone, phenacyl bromide, and primary amine in water. A variety of indole derivatives were prepared using this operationally simple and straight forward methodology in acceptable yields. GRAPHICAL ABSTRACT

  摘要 4-oxo-4,5,6,7-四氢吲哚衍生物的合成通过Wang-OSO3H 介导的三组分反应实现了合成4-oxo-4,5,6,7-四氢吲哚衍生物的绿色方法，该反应涉及水中的二甲酮、苯甲酰溴和伯胺。使用这种操作简单且直接的方法以可接受的产率制备了多种吲哚衍生物。图形概要
• In silico studies and β-cyclodextrin mediated neutral synthesis of 4-oxo-4,5,6,7-tetrahydroindoles of potential biological interest
  作者：G. Dhananjaya、A.V. Dhanunjaya Rao、Kazi Amirul Hossain、Venkateswara Rao Anna、Manojit Pal

  DOI：10.1016/j.tetlet.2020.151972

  日期：2020.6

  Prompted by the in silico docking study predictions the first β-cyclodextrin (β-CD) mediated synthesis of 4-oxo-4,5,6,7-tetrahydroindoles in water was achieved via a 3-component reaction under neutral conditions. A range of compounds was prepared by using this environmentally friendly method in good yields (82–92%). The catalyst β-CD could be recovered and recycled. The in silico docking studies predicted

  通过计算机对接研究的预测，在中性条件下通过3组分反应实现了第一个由β-环糊精（β-CD）介导的水中4-氧代-4,5,6,7-四氢吲哚的合成。使用这种环境友好的方法可以制备出一系列化合物，收率很高（82–92％）。催化剂β-CD可以回收和再循环。的在计算机芯片对接研究预测分支酸变位酶（CM）的一些合成的tetrahydroindoles，是由随后的结果的支持的抑制性质的体外测定法。
• A metal‐free visible light promoted three‐component facile synthesis of 4‐oxo‐tetrahydroindoles in ethanol–water
  作者：Khursheed Ansari、Mohd Nazeef、Shabir Ali、Malik A. Waseem、Wajaht A. Shah、Saif Ansari、Ibadur R. Siddiqui、Jagdamba Singh

  DOI：10.1002/jhet.4202

  日期：2021.2

  A mild and efficient visible light–mediated one‐pot multicomponent tandem approach to construct 4‐oxo‐tetrahydroindoles in ethanol–water medium at room temperature has been described. The characteristics of reported methodology are the utilization of visible light, an ideal source of energy to generate CC and CN bonds from commercially available substrates namely dimedone, phenacyl bromides, and

  已经描述了一种温和有效的可见光介导的单锅多组分串联方法，可在室温下在乙醇-水介质中构建4-氧代-四氢吲哚。所报告方法的特点是利用可见光，这是一种理想的能源，可以从可商购获得的底物，即二甲酮，苯甲酰溴和胺中生成C andC和CN键。所提出的方案与开发4-氧-四氢吲哚衍生物具有高度的兼容性，具有更高的选择性和高收率。此外，无金属合成，环境友好的溶剂，简便的后处理，高原子经济性，成本效益，反应时间短和广泛的底物范围是所报道方案的主要优点。
• Sulfamic acid promoted one-pot multicomponent reaction: a facile synthesis of 4-oxo-tetrahydroindoles under ball milling conditions
  作者：Trimurti L. Lambat、Ahmed A. Abdala、Sami Mahmood、Pankaj V. Ledade、Ratiram G. Chaudhary、Subhash Banerjee

  DOI：10.1039/c9ra08478a

  日期：——

  We report an efficient and facile one-pot synthesis of 4-oxo-tetrahydroindoles using sulfamic acid under ball milling conditions. The present protocol for preparation of biologically important 4-oxo-tetrahydroindoles offers several advantages such as mild reaction conditions, improved selectivity and higher isolated yields. Moreover, solvent-free reaction conditions and the use of ball milling make

  我们报告了在球磨条件下使用氨基磺酸有效且简便的一锅法合成 4-氧代-四氢吲哚。本协议用于制备生物学上重要的 4-氧代-四氢吲哚具有几个优点，例如温和的反应条件、提高的选择性和更高的分离产率。此外，无溶剂反应条件和球磨的使用使本协议本质上对环境友好。
• Synthesis and spectral properties of the 1-aryl-2-phenyl-4-oxo-4,5,6,7-tetrahydroindole oximes and of their beckmann rearrangement products
  作者：C. Dagher、R. Hanna、P. B. Terentiev、Y. G. Boundel、B. I. Maksimov、N. S. Kulikov

  DOI：10.1002/jhet.5570200428

  日期：1983.7

  Under Beckmann conditions the oximes of the 1-aryl-2-phenyl-4-oxo-4,5,6,7-tetrahydroindoles 2a-k are rearranged yielding as the sole product, 1-aryl-2-phenyl-4-oxo-1,4,5,6,7,8-hexahydropyrrolo[3,2-c]azepine 3a-k. The spectral data (ir, uv, ms) of these two classes of compounds are also discussed.

  在贝克曼条件下，将1-芳基-2-苯基-4-氧代4,5,6,7-四氢吲哚2a-k的肟重排，得到唯一的产物1-芳基-2-苯基-4-氧代。 -1,4,5,6,7,8-六氢吡咯并[3,2- c ]氮杂3a-k。还讨论了这两类化合物的光谱数据（ir，uv，ms）。