3‑acetyl‑2,7,7‑trimethyl‑4‑phenyl‑4,6,7,8‑tetrahydroquinoline‑5(1H)‑one | 19732-54-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3‑acetyl‑2,7,7‑trimethyl‑4‑phenyl‑4,6,7,8‑tetrahydroquinoline‑5(1H)‑one
• 英文别名: 3-acetyl-2,7,7-trimethyl-4-phenyl-4,6,7,8-tetrahydro-1H-quinolin-5-one；3-ethanoyl-4-phenyl-2,7,7-trimethyl-4,6,7,8-tetrahydro-5(1H)-quinolone；3-acetyl-2,7,7-trimethyl-4-phenyl-4,6,7,8-tetrahydro-5(1H)-quinolinone；3-acetyl-2,7,7-trimethyl-4-phenyl-1,4,6,8-tetrahydroquinolin-5-one
• CAS: 19732-54-8
• 化学式: C₂₀H₂₃NO₂
• 分子量: 309.408
• InChiKey: NJMBVVVLSJLFOA-UHFFFAOYSA-N

物化性质

• 熔点：
  198-200 °C
• 沸点：
  476.2±45.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  乙酰丙酮 在 ammonium acetate 作用下， 以 乙醇 为溶剂， 反应 3.33h， 生成 3‑acetyl‑2,7,7‑trimethyl‑4‑phenyl‑4,6,7,8‑tetrahydroquinoline‑5(1H)‑one
  参考文献：
  名称：

  Efficient synthesis of decahydroacridine-1,8-diones and polyhydroquinolines using the step-wise method

  摘要：

  通过两步环化缩合反应合成了多种对称的和非对称的十氢吖啶-1,8-二酮和多氢喹啉衍生物。与其它一步合成反应相比，逐步加入反应物的优势在于避免形成2或3个不希望的副产品，从而实现了更清洁的反应处理。这种高效环化缩合方法的关键因素是，将制备的β-烯胺酮组分逐滴加入到溶液中，在该溶液中醛分子与1,3-二羰基化合物反应逐渐形成Knoevenagel缩合产物。将提出的逐步方法的结果与一步合成反应所得结果进行比较和讨论。

  DOI：

  10.1007/s11164-021-04643-z

文献信息

• Novel SO₃H-Functionalized Ionic Liquids - Catalyzed Facile and Efficient Synthesis of Polyhydroquinoline Derivatives via Hantzsch Condensation under Ultrasound Irradiation
  作者：Bai Lin Li、Ai Guo Zhong、An Guo Ying

  DOI：10.1002/jhet.2070

  日期：2015.3

  A facile and efficient synthesis of polyhydroquinolines has been developed via four‐component condensation reactions of aldehydes, dimedone, ethyl acetoacetate, and ammonium acetate in the presence of Novel SO3H‐functionalized ionic liquid catalysts through Hantzsch reaction under ultrasound irradiation without solvent. Simple work‐up procedure, environmentally friendly, inexpensive, and non‐toxic

  在新型SO 3 H官能化离子液体催化剂存在下，通过Hantzsch反应，在无溶剂的情况下，通过Hantzsch反应，通过醛，二甲酮，乙酰乙酸乙酯和乙酸铵的四组分缩合反应，开发了一种简便高效的聚氢喹啉合成方法。该实用方法的重要特点是操作步骤简单，环保，廉价且无毒的催化剂，较短的反应时间以及优异的产品收率。
• 5-Pyrrolidin-2-yltetrazole-Promoted One-Pot Hantzsch Polyhydroquinoline Synthesis Using NH4HCO3 as Nitrogen Source
  作者：Weike Su、Jia Li、Jianjun Li

  DOI：10.1071/ch08197

  日期：——

  A straightforward and green synthesis of polyhydroquinoline derivatives was reported via a four-component coupling reaction of aldehydes, dimedone, active methylene compounds, and ammonium bicarbonate in the presence of 5-pyrrolidin-2-yltetrazole under solvent-free conditions. The method offers several advantages including high yields, an environmental friendly procedure, a short reaction time, and easy isolation of products.

  在无溶剂条件下，5-吡咯烷-2-基四氮唑存在下，通过醛、二甲基酮、活性亚甲基化合物和碳酸氢铵的四组分偶联反应，报道了一种直接、绿色的多氢喹啉衍生物合成方法。该方法具有收率高、程序环保、反应时间短和易于分离产物等优点。
• [EN] QUINOLONE AND ACRIDINONE DERIVATIVES FOR THE TREATMENT OF URINARY INCONTINENCE<br/>[FR] DERIVES DE QUINOLONE ET D'ACRIDINONE UTILISES DANS LE TRAITEMENT DE L'INCONTINENCE URINAIRE
  申请人：ZENECA LIMITED

  公开号：WO1994008966A1

  公开（公告）日：1994-04-28

  (EN) Compounds of Formula (I) wherein R2, R3, R4, R10 and R11 have any of the meanings given in the specification, and their pharmaceutically acceptable salts are useful in the treatment of urinary incontinence. Also disclosed are pharmaceutical compositions, processes for preparing the compounds of Formula (I) and intermediates.(FR) Composés de la formule (I) dans laquelle R2, R3, R4, R10 et R11 ont les notations données dans le descriptif de l'invention. Ces composés et leurs sels pharmaceutiquement acceptables peuvent être utilisés dans le traitement de l'incontinence urinaire. Des compositions pharmaceutiques, des procédés de préparation des composés de la formule (I) et des intermédiaires sont également décrits.

  (EN) 公式(I)的化合物，其中R2、R3、R4、R10和R11具有规范中给出的任何含义，它们的药学上可接受的盐在治疗尿失禁方面有用。还公开了制备公式(I)化合物和中间体的药物组合物和过程。 (FR) 公式(I)中R2、R3、R4、R10和R11具有规范中给出的任何含义的化合物及其药学上可接受的盐可用于治疗尿失禁。还描述了药物组合物、制备公式(I)化合物和中间体的过程。
• Methyl 2,7,7-Trimethyl-4-(3-nitrophenyl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate and 3-Acetyl-2,7,7-trimethyl-4-phenyl-1,4,5,6,7,8-hexahydro-5-quinolone
  作者：A. D. Morales、S. García-Granda、M. S. Navarro、A. M. Diviú、R. E. Pérez-Barquero

  DOI：10.1107/s0108270196004611

  日期：1996.9.15

  The 1,4-dihydropyridine (1,4-DHP) ring and the cyclohexanone ring adopt similar conformations in both the title compounds, methyl 2,7,7-trimethyl-4-(3-nitrophenyl)-5-oxo-1 4,5,6,7,8-hexahydroquinoline-3-carboxylate, C20H22N2O5, (I) and 3-acetyl-2,7,7-trimethyl-4-phenyl-1 ,4,5,6,7,8-hexahydro-5-quinolone, C20H23NO2, (II). The 1,4-DHP rings have boat conformations with the aryl group occupying the pseudo-axial position and orthogonal to the plane through the 1,4-DHP ring. The cyclohexanone ring has an intermediate half-chair/sofa form, In both compounds, the carboxyl group is coplanar to the endocyclic double bond as a consequence of ir conjugation, The molecules are linked by N-H ... O hydrogen bonds but the packing is different in each case, In compound (I) a hydrogen bond is formed between the N-H and the carboxyl group while in compound (II), a hydrogen bond is formed between the N-H and the O atom of the cyclohexanone ring.
• QUINOLONE DERIVATIVE FOR TREATMENT OF URINARY INCONTINENCE
  申请人：AstraZeneca AB

  公开号：EP0755382B1

  公开（公告）日：2001-06-13