3-<(4'-chlorophenyl)amino>-5-methyl-2-cyclohexen-1-one

• 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-<(4'-chlorophenyl)amino>-5-methyl-2-cyclohexen-1-one
• 英文别名: 3-((4-chlorophenyl)amino)-5-methylcyclohex-2-en-1-one；DM 27；3-(4-Chloroanilino)-5-methylcyclohex-2-en-1-one
• 化学式: C₁₃H₁₄ClNO
• 分子量: 235.713
• InChiKey: YPHPEIMMVSEBTK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 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-<(4'-chlorophenyl)amino>-5-methyl-2-cyclohexen-1-one 在 溶剂黄146 、 三氟乙酸 作用下， 反应 0.47h， 以84%的产率得到11-(4-chlorophenyl)-9-methyl-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
• 作为产物：
  描述：

  4-(4-氯苯胺基)-6-甲基-2-氧代环己-3-烯-1-羧酸乙酯 在 porcine liver esterase (EC 3.1.1.1) 作用下， 以 水 为溶剂， 反应 8.0h， 生成 3-<(4'-chlorophenyl)amino>-5-methyl-2-cyclohexen-1-one
  参考文献：
  名称：

  烯胺酮的合成和抗惊厥活性。第7部分。4-[（取代的苯基）氨基] -6-甲基-2-氧代环己基-3-烯-1-羧酸乙酯及其相应的5-甲基环己-2-烯酮衍生物的合成和抗惊厥性评价。

  摘要：

  试图进一步研究烯胺酮的潜在抗惊厥活性，以发现代谢产物作为烯胺酮的酯的活性/共活性实体的可能作用。合成了一系列5-甲基-2-环己烯烯酮，它们是假设的代谢产物，对应于一系列活性和非活性酯，并评估了其抗惊厥活性。4-[（4-氰基苯基）氨基] -6-甲基-2-氧代环己基-3-烯-1-羧酸乙酯（1k）和3- [N-（4-氰基苯基）氨基] -5 -惊厥药-甲基-2-环己烯酮（3g）和乙基4-（苯氨基）-6-甲基-2-环己烯酮（1n）和3-N-（苯基氨基）-5-甲基-2-环己烯酮（3j）筛选数据是平行的，酯及其推定的脱羧类似物显示出相似的活性。本系列中评估最活跃的类似物，4-[（4-氯苯基）氨基] -6-甲基-2-氧代环己基-3-烯-1-羧酸乙酯（1e），其ED（50）为16.7 mg kg（-1）和TD（小鼠最大电击发作（MES）测试中110.7 mg kg（-1）（保护指数，PI = TD（50）/

  DOI：

  10.1016/s0223-5234(02)00006-5

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。
• A Reusable CNT‐Supported Single‐Atom Iron Catalyst for the Highly Efficient Synthesis of C−N Bonds
  作者：Qifeng Ding、Yang Yu、Fei Huang、Lihui Zhang、Jian‐Guo Zheng、Mingjie Xu、Jonathan B. Baell、He Huang

  DOI：10.1002/chem.201905468

  日期：2020.4.6

  reaction, which is important for the synthesis of nitrogen-containing molecules in both organic and pharmaceutical chemistry. Noble metal and homogeneous catalysts have been used for C-N bond formation frequently, however, there are still some problems for these catalysts such as high cost, serious pollution and low atom economy. Herein the low-toxic and cheaper iron complex was loaded on CNTs and the heterogenous

  CN键的形成被认为是非常有用且基本的反应，这对于有机化学和药物化学中含氮分子的合成非常重要。贵金属和均相催化剂经常被用于形成CN键，但是，这些催化剂仍然存在一些问题，例如成本高，污染严重和原子经济性低。在此将低毒且便宜的铁络合物负载在CNT上，并制备了名为Fe-N x / CNTs的异质单原子催化剂（SAC）。我们首次将这种SAC应用于CN键的合成。发现Fe-N x / CNTs是从芳族胺和酮合成CN键的有效催化剂。催化性能非常出色，产率高达96％，比贵金属催化剂（例如AuCl 3 / CNT和RhCl 3 / CNT）高6倍。它适用于多达13种不含添加剂的芳族胺底物，并获得17种烯胺酮。通过将高角度环形暗场扫描透射电子显微镜（HAADF-STEM）与X射线吸收光谱法（XAS）结合使用，我们观察到Fe-N x / CNTs的铁物种分散良好，因为单原子和Fe- N x可能是催化活性位点。该Fe-N
• Synthesis and anticonvulsant activity of enaminones. 2. Further structure-activity correlations
  作者：K. R. Scott、Ivan O. Edafiogho、Erica L. Richardson、Vida A. Farrar、Jacqueline A. Moore、Elizabeth I. Tietz、Christine N. Hinko、Hyejung Chang、Afif El-Assadi、Jesse M. Nicholson

  DOI：10.1021/jm00066a003

  日期：1993.7

  shown to be safer alternatives, the most notable was methyl 4-[(p-bromophenyl)amino]-6-methyl-2-oxocyclohex-3-en-1-oate, 13. Compound 13 had an ip ED50 of 4 mg/kg in the rat and a TD50 of 269 mg/kg, providing a protective index (TD50/ED50) of > 67. By variation in the ring size, additional aromatic substitutions and the synthesis of acyclic analogs, these newer compounds provide a more definitive insight

  该报告继续对4-[（对氯苯基）氨基] -6-甲基-2-氧代环己基-3-烯-1-酸酯1（ADD 196022）和甲基4-（苄基氨基）进行深入评估-6-甲基-2-氧代环己基-3-烯-1-酸酯，2个，两个有效的抗惊厥性烯胺酮。这些化合物采用杏仁核点燃模型进行评估。1和2都没有针对杏仁核点燃的癫痫发作的活性，进一步支持了角膜点燃的模型作为抗电击癫痫发作评估的确定工具，如先前报道。关于1的其他腹膜内（ip）数据显示，在100 mg / kg的24小时内有毒性。为了使毒性最小化，已经制备了几种活性类似物。在由抗癫痫药物开发（ADD）计划开发的特殊ip大鼠屏幕中，对这些新的类似物进行了评估，以防最大剂量10 mg / kg的电击惊厥（MES）和100 mg / kg的神经毒性。从该筛选中，显示出几种化合物是更安全的替代品，最引人注目的是4-[（（对-溴苯基）氨基] -6-甲基-2-氧代环己基-3-en-
• Ultraviolet spectroscopy of anticonvulsant enaminones
  作者：I.O Edafiogho、O.A Phillips、M Abdel-Hamid、A.A.M Ali、W.C Matowe、A El-Hashim、S.B Kombian

  DOI：10.1016/s0968-0896(01)00314-5

  日期：2002.3

  The ultraviolet (UV) spectra of selected enaminones were determined in acidic, alkaline and neutral media and compared to their anticonvulsant activities. The wavelength of maximum absorption and molar absorptivity were compared with the anticonvulsant activity of the selected secondary and tertiary enaminones. and general inferences were made. The UV spectra of the enaminones had hypsochromic shifts in acidic media in comparison with neutral media. Generally, a small hypsochromic shift occurred in alkaline media when compared to the neutral solutions of the enaminones. The tertiary enaminones absorbed UV light at longer wavelength than the secondary enaminones in acidic, neutral and alkaline media. In particular, the tertiary enaminones displayed absorption at the higher end and secondary enaminones towards the lower end of the UV wavelength range 292-315 nm in aqueous media. Tertiary enaminones (30-33) which were devoid of the NH proton were found to be uniformly inactive in a mouse model of electroshock seizures, while some secondary enaminones (1, 5-8, 12. 16, 18, 20, 23-25, 28 and 29) had anticonvulsant activity. Thus the NH group of secondary enaminones is very important for anticonvulsant activity, and this agrees with an already established trend in proton NMR spectroscopy. In addition, the pares-substitution on the phenyl group in some enaminones result in higher molar absorptivity (a) values that enhance anticonvulsant activity. These results indicate that the anticonvulsant activity of enaminones is not due to electronic effect alone, but is probably due to a combination of factors including electronic and steric effects. lipophilicity, and hydrogen bonding. (C) 2002 Elsevier Science Ltd. All rights reserved.
• US5468775A
  申请人：——

  公开号：US5468775A

  公开（公告）日：1995-11-21