3-(4-chlorophenylamino)-3-phenyl-1-(4-nitrophenylpropan)-1-one | 4210-10-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 3-(4-chlorophenylamino)-3-phenyl-1-(4-nitrophenylpropan)-1-one
• 英文别名: 3-phenyl-3-(4-chloroanilino)-1-(4-nitrophenyl)-1-acetone；3-(4-Chloroanilino)-1-(4-nitrophenyl)-3-phenylpropan-1-one
• CAS: 4210-10-0
• 化学式: C₂₁H₁₇ClN₂O₃
• 分子量: 380.831
• InChiKey: LSYPCIHKAMGEMY-UHFFFAOYSA-N

物化性质

• 熔点：
  150-151 °C
• 沸点：
  586.7±50.0 °C(Predicted)
• 密度：
  1.328±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-chlorophenylamino)-3-phenyl-1-(4-nitrophenylpropan)-1-one 、 2-(三甲基硅)苯基三氟甲烷磺酸盐 在 potassium fluoride 、 18-冠醚-6 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以63%的产率得到1-(4-chlorophenyl)-4-(4-nitrophenyl)-2-phenyl-1,2,3,4-tetrahydroquinolin-4-ol
  参考文献：
  名称：

  Diastereoselective Synthesis of N-Aryl Tetrahydroquinolines and N-Aryl Indolines by the Tandem Reaction of Arynes

  摘要：

  A tandem reaction of arynes with α- or β-amino ketones has been revealed. Arynes react with β-amino ketones through a cascade insertion-cyclization process to afford N-aryl tetrahydroquinolines in good yield with excellent anti-selectivity. Meanwhile, the coupling of arynes with α-amino ketones produces multisubstituted indolines in high yield with syn-selectivity. A quaternary carbon center can be constructed in this process, and the reaction can be easily scaled up.

  DOI：

  10.1021/jo5003399
• 作为产物：
  描述：

  1-(4-nitro-phenyl)-3-phenyl-propenone 、 对氯苯胺 以 乙醇 为溶剂， 反应 1.08h， 生成 3-(4-chlorophenylamino)-3-phenyl-1-(4-nitrophenylpropan)-1-one
  参考文献：
  名称：

  K3PO4-catalyzed one-pot synthesis of β-amino ketones

  摘要：

  A new strategy which uses cheap K3PO4 as a very effective catalyst has been developed for synthesis of beta-amino ketones by one-pot reaction of an aryl aldehyde, acetophenone derivative, and amine in EtOH at room temperature.

  DOI：

  10.1007/s00706-012-0729-1

文献信息

• Three-Component Mannich Reaction of Aromatic Ketones, Aldehydes and Amines Catalyzed by Reusable Aluminium Methanesulfonate
  作者：Min Wang、Zhi-Guo Song、Heng Jiang

  DOI：10.1080/00304940903078111

  日期：2009.7.22

  derived from aromatic ketones, aldehydes and amines can only be realized indirectly by “amine exchange reaction” or “the addition of ketones to Schiff bases”.3,4 Yi and co-workers described the three-component Mannich reaction of aromatic ketones, aldehydes and amines could be catalyzed by HCl/EtOH in 1991.5 Since then, the Mannich reaction has been expanded to include various ketones, aldehydes and amines

  曼尼希反应已经扩展到包括使用 HCl/EtOH 的各种酮、醛和胺。6 然而，使用 HCl/EtOH 的曼尼希碱的盐酸盐在放置时不稳定。5 此外，盐酸对环境不友好。因此，已经报道了这些多取代曼尼希碱的更实用的合成方法，使用十二烷基苯磺酸、7 聚苯乙烯-SO3H、NbCl5、Re(PFO)3、Re(OPf)3、酸性离子液体、12 H3PW12O40、NaBAr4、 SiO2-OAlCl2、QAS Gemini 含氟表面活性剂、16 等。但是，催化剂过量、试剂昂贵、反应时间长、收率低等缺点仍然存在。此外，由于空间效应，邻位取代的芳香胺的曼尼希反应没有得到所需的产物。此外，传统的路易斯酸不能使用，因为在亚胺形成过程中存在游离胺和水。因此，从原子经济和环境的角度来看，需要为直接一锅曼尼希反应开发一种新的有效系统。
• Non-Steroidal Androgen Receptor Modulators, Preparation Process, Pharmaceutical Composition and Use Thereof
  申请人：Wang Mingwei

  公开号：US20080293808A1

  公开（公告）日：2008-11-27

  Non-steroidal androgen receptor modulating compounds of the general formula (I), their pharmaceutically acceptable salts, preparation process and pharmaceutically compositions containing the said compounds are disclosed. Such compounds of the general formula (I) or their pharmaceutically acceptable salts can be used for preparing non-steroidal medicines to treat and/or prevent conditions or diseases such as prostatic hyperplasia, prostate cancer, hirsutism, severe hormone-dependent alopecia or acne, etc. as a result of androgen receptor antagonistic activities.

  一般式(I)的非类固醇雄激素受体调节化合物、其药学上可接受的盐、制备过程以及含有上述化合物的药学组合物已被披露。一般式(I)的这种化合物或其药学上可接受的盐可用于制备非类固醇药物，用于治疗和/或预防前列腺增生、前列腺癌、多毛症、严重依赖激素的脱发或痤疮等疾病，因其雄激素受体拮抗活性而产生的效果。
• Wang, Min; Liang, Yan; Song, Zhiguo, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2010, vol. 49, # 12, p. 1653 - 1656
  作者：Wang, Min、Liang, Yan、Song, Zhiguo

  DOI：——

  日期：——
• SnCl₄·5H₂O-CATALYZED SYNTHESIS OF<i>β</i>-AMINO CARBONYL COMPOUNDS VIA A DIRECT MANNICH-TYPE REACTION
  作者：Min Wang、Zhiguo Song、Yan Liang

  DOI：10.1080/10826068.2010.489008

  日期：2010.12.29

  An efficient three-component, one-pot synthesis of beta-amino carbonyl compounds from aromatic ketones, aromatic aldehydes; and aromatic amines using tin tetrachloride at room temperature in ethanol is described. The advantages of the new method are good yields (62-96%), simple workup, and inexpensive catalyst.
• EP1889829
  申请人：——

  公开号：——

  公开（公告）日：——