3-[(3,5-Dichlorophenyl)amino]-5,5-dimethylcyclohex-2-en-1-one | 443908-53-0

• 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: 3-[(3,5-Dichlorophenyl)amino]-5,5-dimethylcyclohex-2-en-1-one
• 英文别名: 3-(3,5-dichloroanilino)-5,5-dimethylcyclohex-2-en-1-one
• CAS: 443908-53-0
• 化学式: C₁₄H₁₅Cl₂NO
• 分子量: 284.185
• InChiKey: QPDHSSRWWRORRC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  水合茚三酮 、 3-[(3,5-Dichlorophenyl)amino]-5,5-dimethylcyclohex-2-en-1-one 在 溶剂黄146 、 三氟乙酸 作用下， 反应 0.4h， 以77%的产率得到11-(3,5-dichlorophenyl)-9,9-dimethyl-9,10-dihydroisochromeno[4,3-b]indole-5,7(8H,11H)-dione
  参考文献：
  名称：

  Domino bicyclization of 2,2-dihydroxyindene-1,3-dione with cyclic enaminones leading to isochromeno[4,3-b]indoles

  摘要：

  New and practical acid-promoted domino bicyclization between 2,2-dihydroxyindene-1,3-dione and cyclic enaminones has been established for the formation of tetracyclic isochromeno[4,3-b]indoles under microwave heating. The present method simultaneously installs C-N, C-O, and C-C bonds, allowing direct assemble of functionalized isochromeno[4,3-b]indole skeleton with a wide diversity in substituents. The reaction features reliable scalability, flexibility of structural modification, and wide substrate scope as well as operational simplicity, and it can avoid time-consuming and costly syntheses, tedious work-up, and isolation of intermediate. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.11.005

文献信息

• Domino reactions of cyclic enaminones leading to selective synthesis of pentacyclic indoles and its functionalization
  作者：Wei Fan、Yan-Rong Li、Qun Li、Bo Jiang、Guigen Li

  DOI：10.1016/j.tet.2016.06.058

  日期：2016.8

  established, providing selective protocol to pentacyclic indoles with different substituted patterns (up to 50 examples). Both substitutions on the cyclic enaminone ring and reaction temperatures showed obvious impact on the reaction pathways. For instance, selective allylic hydroxylation and allylic esterification of in situ generated indoles depend on reaction temperatures. With special substituents

  建立了在酸酐溶剂中环状烯胺酮与1,2-二酮的新的多组分多米诺骨牌反应，为具有不同取代方式的五环吲哚提供了选择性方案（最多50个实例）。环状烯胺环上的两个取代和反应温度都对反应路径有明显的影响。例如，原位生成的吲哚的选择性烯丙基羟基化和烯丙基酯化取决于反应温度。在具有特殊取代基的情况下，反应进行脱氢过程，从而可以以良好或优异的产率获得不同的取代稠合吲哚。这些反应具有温和的条件，方便的一锅操作和较短的反应时间。
• Synthesis of Diastereoenriched Oxazolo[5,4-<i>b</i>]indoles via Catalyst-Free Multicomponent Bicyclizations
  作者：Lu Wang、Li-Xia Shi、Lu Liu、Zhuo-Xuan Li、Ting Xu、Wen-Juan Hao、Guigen Li、Shu-Jiang Tu、Bo Jiang

  DOI：10.1021/acs.joc.7b00129

  日期：2017.4.7

  These microwave-assisted transformations in environmentally compatible ethanol resulted in continuous multiple bond-forming events including C–C, C–N, and C–O bonds, enabling catalyst-free multicomponent bicyclizations to rapidly build up functional N,O-heterocycles.

  从具有环烯胺酮和氨基酸的简单易得的芳基乙二醛中，已经公开了一种新的，高度环保的方法，该方法具有高收率和高非对映选择性（高达> 99：1），可用于多样化和功能化的恶唑并[5,4- b ]吲哚。这些在环境相容的乙醇中的微波辅助转化导致连续的多个键形成事件，包括C–C，C–N和C–O键，从而使无催化剂的多组分双环化能够快速建立功能性的N，O-杂环。
• Highly Selective Domino Multicyclizations for Forming Polycyclic Fused Acridines and Azaheterocyclic Skeletons
  作者：Bo Jiang、Xue Wang、Hai-Wei Xu、Man-Su Tu、Shu-Jiang Tu、Guigen Li

  DOI：10.1021/ol400322v

  日期：2013.4.5

  Highly selective four-component domino multicyclizations for the synthesis of new fused acridines and azaheterocyclic skeletons have been established by mixing common reactants in isobutyric acid under microwave irradiation. The reactions proceed at fast rates and were conducted to completion within 20-30 min. Up to seven new chemical bonds, four rings, and four stereocenters were assembled in a convenient one-pot operation. The resulting hexacyclic and pentacyclic fused acridines and their stereochemistry have been fully characterized and determined by X-ray structural analysis.
• A new and efficient domino strategy to indole derivatives synthesis and its C3-bisfunctionalization
  作者：Li-Yuan Xue、Bo Jiang、Man-Su Tu、Shu-Jiang Tu

  DOI：10.1016/j.tetlet.2012.09.120

  日期：2012.11

  A series of new poly-functionalized indole derivatives were synthesized via domino reactions of alloxan monohydrate and N-aryl substituted enaminones in HOAc at room temperature. The direct C3-bisfunctionalization of indole ring was achieved in a one-pot operation. The reaction is easy to perform simply by mixing common reactants in acetic acid. The reaction proceeds at fast rates and can be finished within 24 min, which makes workup convenient to give good to excellent chemical yields. (C) 2012 Elsevier Ltd. All rights reserved.
• Domino bicyclization of 2,2-dihydroxyindene-1,3-dione with cyclic enaminones leading to isochromeno[4,3-b]indoles
  作者：Fu-Jie Zhao、Mu-Yan Sun、Yi-Jing Dang、Xiao-Yan Meng、Bo Jiang、Wen-Juan Hao、Shu-Jiang Tu

  DOI：10.1016/j.tet.2014.11.005

  日期：2014.12

  New and practical acid-promoted domino bicyclization between 2,2-dihydroxyindene-1,3-dione and cyclic enaminones has been established for the formation of tetracyclic isochromeno[4,3-b]indoles under microwave heating. The present method simultaneously installs C-N, C-O, and C-C bonds, allowing direct assemble of functionalized isochromeno[4,3-b]indole skeleton with a wide diversity in substituents. The reaction features reliable scalability, flexibility of structural modification, and wide substrate scope as well as operational simplicity, and it can avoid time-consuming and costly syntheses, tedious work-up, and isolation of intermediate. (C) 2014 Elsevier Ltd. All rights reserved.