3-(3-Chloro-4-methoxy-phenylamino)-5,5-dimethyl-cyclohex-2-enone | 153865-39-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(3-Chloro-4-methoxy-phenylamino)-5,5-dimethyl-cyclohex-2-enone
• 英文别名: 3-(3-Chloro-4-methoxyanilino)-5,5-dimethylcyclohex-2-en-1-one
• CAS: 153865-39-5
• 化学式: C₁₅H₁₈ClNO₂
• 分子量: 279.766
• InChiKey: DJZBZMHFZUJEAM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(3-Chloro-4-methoxy-phenylamino)-5,5-dimethyl-cyclohex-2-enone 在 sodium amide 、 sodium t-butanolate 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以62%的产率得到6-methoxy-2,2-dimethyl-2,3-dihydro-1H-carbazol-4(9H)-one
  参考文献：
  名称：

  复杂的碱促进卤代亚胺或烯胺的芳烃环化：吲哚衍生物的区域化学合成

  摘要：

  复杂的碱式NaNH 2 -tBuONa可以通过亚胺或氯苯胺的烯胺的芳基环化反应迅速合成吲哚衍生物。不稳定，无需纯化即可使用，复杂的碱对杂质不敏感。

  DOI：

  10.1016/s0040-4039(00)91822-7
• 作为产物：
  描述：

  5,5-二甲基-1,3-环己二酮 、 3-氯-4-甲氧基苯胺 在 APTS 作用下， 以 苯 为溶剂， 生成 3-(3-Chloro-4-methoxy-phenylamino)-5,5-dimethyl-cyclohex-2-enone
  参考文献：
  名称：

  Aggregative activation and heterocyclic chemistry I complex bases promoted arynic cyclisation of imines or enaminoketones; regiochemical synthesis of indoles

  摘要：

  The complex base NaNH2-t-BuONa allowed expeditious syntheses of indoles by arynic cyclisation of imines or enaminoketones prepared from halogeno anilines and carbonyl derivatives. Unstable imines may be used without purification, complex bases being unsensitive to impurities. It is showed that this kind of reaction may be applied to mixture of substrates suitably halogenated on the benzene ring. Formation of three components aggregates is proposed to explain a number of observations.

  DOI：

  10.1016/s0040-4020(01)89304-2

文献信息

• Complex bases promoted arynic cyclisations of halogenated imines or enamines: A regiochemical synthesis of indole derivatives
  作者：Catherine Caubère、Paul Caubère、Pierre Renard、Jean-Guy Bizot-Espiart、Brigitte Jamart-Grégoire

  DOI：10.1016/s0040-4039(00)91822-7

  日期：1993.10

  The complex base NaNH2-tBuONa allows expeditious synthesis of indole derivatives by arynic cyclization of imines or enamines of chloroanilines. Unstable may be used without purification, complex bases being unsensitive to impurities.

  复杂的碱式NaNH 2 -tBuONa可以通过亚胺或氯苯胺的烯胺的芳基环化反应迅速合成吲哚衍生物。不稳定，无需纯化即可使用，复杂的碱对杂质不敏感。
• 10.1039/d4nj01583e
  作者：Sinha, Goutam、Pramanik, Sayan、Jana, Debashis、Ghosh, Anirban、Mukhopadhyay, Chhanda

  DOI：10.1039/d4nj01583e

  日期：——

  indole-2,4-diones from readily available β-enaminones and glyoxal and subsequent I2/DMSO-mediated oxidation/aromatization of tetrahydro indole-2,4-dione to produce 4-hydroxyisatin derivatives. The key aspect of this protocol includes the dual catalytic activity of molecular iodine in the presence of DMSO. Mechanistic study suggested that this reaction is substrate selective as corresponding aromatization

  我们报道了一种从容易获得的β-烯胺酮和乙二醛合成四氢吲哚-2,4-二酮的有效合成路线，以及随后的I 2 /DMSO介导的四氢吲哚-2,4氧化/芳构化-二酮生产4-羟基靛红衍生物。该协议的关键方面包括分子碘在 DMSO 存在下的双重催化活性。机理研究表明，该反应具有底物选择性，因为相应的芳构化和 sp 3 C-H 氧化在 6,6-二取代四氢吲哚-2,4-二酮存在下停止。此外，对 β-烯胺酮和乙二醛进行酸催化环化/脱水/烯醇-酮互变异构反应后合成四氢吲哚-2,4-二酮进行了彻底的研究。
• Aggregative activation and heterocyclic chemistry I complex bases promoted arynic cyclisation of imines or enaminoketones; regiochemical synthesis of indoles
  作者：Catherine Caubère、Paul Caubère、Sandra Ianelli、Mario Nardelli、Brigitte Jamart-Grégoire

  DOI：10.1016/s0040-4020(01)89304-2

  日期：1994.1

  The complex base NaNH2-t-BuONa allowed expeditious syntheses of indoles by arynic cyclisation of imines or enaminoketones prepared from halogeno anilines and carbonyl derivatives. Unstable imines may be used without purification, complex bases being unsensitive to impurities. It is showed that this kind of reaction may be applied to mixture of substrates suitably halogenated on the benzene ring. Formation of three components aggregates is proposed to explain a number of observations.