3-(3-chloro-4-methylphenylamino)-5,5-dimethylcyclohex-2-enone | 166883-86-9

• 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-chloro-4-methylphenylamino)-5,5-dimethylcyclohex-2-enone
• 英文别名: 3-[(3-Chloro-4-methylphenyl)amino]-5,5-dimethylcyclohex-2-en-1-one；3-(3-chloro-4-methylanilino)-5,5-dimethylcyclohex-2-en-1-one
• CAS: 166883-86-9
• 化学式: C₁₅H₁₈ClNO
• mdl: MFCD03016373
• 分子量: 263.767
• InChiKey: LEGBHXGPDYDBEO-UHFFFAOYSA-N

物化性质

• 溶解度：
  16.2 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  3-(3-chloro-4-methylphenylamino)-5,5-dimethylcyclohex-2-enone 在 sodium hydride 、 sodium amide 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 66.0h， 生成 1,2,3,9-tetrahydro-4,4,6,9-tetramethyl-2H-carbazol-2-one
  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
• 作为产物：
  描述：

  5,5-二甲基-1,3-环己二酮 、 3-氯-4-甲基苯胺 在 phosphomolybdic acid 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以90%的产率得到3-(3-chloro-4-methylphenylamino)-5,5-dimethylcyclohex-2-enone
  参考文献：
  名称：

  Phosphomolybdic Acid (PMA) Catalyzed Highly Efficient and Rapid Synthesis of β-Enaminones

  摘要：

  beta-Enamino derivatives have been synthesized by the condensation of amines and beta-dicarbonyl compounds in the presence of 1 mol% of phosphomolybdic acid (PMA) at room temperature in good to excellent yields.

  DOI：

  10.1080/00397911.2010.524339

文献信息

• Efficient Synthesis of Functionalized Dihydro-1<i>H</i>-indol-4(5<i>H</i>)-ones via One-Pot Three-Component Reaction under Catalyst-Free Conditions
  作者：Hui-Yan Wang、Da-Qing Shi

  DOI：10.1021/co4000198

  日期：2013.5.13

  A facile and efficient one-pot procedure for the preparation of functionalized dihydro-1H-indol-4(5H)-ones by a catalyst-free, three-component reaction of 1,3-dicarbonyl compounds, arylglyoxal monohydrate and enaminones under mild conditions in excellent yield is reported. This synthesis was confirmed to follow the group-assisted-purification (GAP) chemistry process, which can avoid traditional purifications

  一种简便有效的一锅法，用于在温和条件下通过无催化剂的1,3-二羰基化合物，芳基乙二醛一水合物和烯胺酮的三组分反应制备官能化的二氢-1H-吲哚-4（5H）-酮据报道，其收率极高。证实该合成遵循组辅助纯化（GAP）化学过程，该过程可避免传统的纯化，色谱法和重结晶。
• Efficient Synthesis of Functionalized Benzo[<i>b</i>][1,8]naphthyridine Derivatives via Three-Component Reaction Catalyzed by <scp>l</scp>-Proline
  作者：Lei Fu、Wei Lin、Ming-Hua Hu、Xue-Cheng Liu、Zhi-Bin Huang、Da-Qing Shi

  DOI：10.1021/co4001524

  日期：2014.5.12

  A facile and efficient one-pot procedure for the preparation of functionalized benzo[b][1,8]naphthyridine derivatives by three-component reaction of 2-chloroquinoline-3-carbaldehyde, 1,3-dicarbonyl compounds, and enaminones catalyzed by l-proline is described. This new protocol has the advantages of environmental friendliness, good yields, and convenient operation.
• Shi, Chunling; Chen, Hui; Li, Yan, Journal of Chemical Research, 2008, # 9, p. 534 - 537
  作者：Shi, Chunling、Chen, Hui、Li, Yan、Shi, Daqing、Ji, Min

  DOI：——

  日期：——
• An efficient one-pot three-component synthesis of tetrahydrofuro[3,4-b]quinoline-1,8(3H,4H)-dione derivatives catalyzed by L-proline
  作者：Chun-Ling Shi、Hui Chen、Daqing Shi

  DOI：10.1002/jhet.782

  日期：2012.1

  AbstractL‐Proline is found to be an efficient catalyst for the synthesis of tetrahydrofuro[3,4‐b]quinoline‐1,8(3H,4H)‐dione derivatives. This protocol is novel and has the advantages of mild condition, high yield, and easy operation. J. Heterocyclic Chem., (2012).
• 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.