3-acetyl-6-chloroquinolin-4(1H)-one | 872789-08-7

• 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-6-chloroquinolin-4(1H)-one
• 英文别名: 3-acetyl-6-chloro-4(1H)-quinolinone；3-acetyl-6-chloro-1H-quinolin-4-one
• CAS: 872789-08-7
• 化学式: C₁₁H₈ClNO₂
• 分子量: 221.643
• InChiKey: PREVFBIXYZGMJO-UHFFFAOYSA-N

物化性质

• 熔点：
  300 °C
• 沸点：
  369.1±37.0 °C(Predicted)
• 密度：
  1.396±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-acetyl-6-chloroquinolin-4(1H)-one 、 4-氟溴苄 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以92%的产率得到3-acetyl-6-chloro-1-(4-fluorophenyl)methyl-4(1H)-quinolinone
  参考文献：
  名称：

  Novel Quinolinonyl Diketo Acid Derivatives as HIV-1 Integrase Inhibitors: Design, Synthesis, and Biological Activities

  摘要：

  Novel quinolinonyl diketo acids were designed to obtain integrase (IN) inhibitors selectively active against the strand transfer (ST) step of the HIV integration process. Those new compounds are characterized by a single aryl diketo acid (DKA) chain in comparison to 4, a bifunctional diketo acid reported by our group as an anti-IN agent highly potent against both the 3'-processing and ST steps. Compound 6d was the most potent derivative in IN enzyme assays, while 6i showed the highest potency against HIV-1 in acutely infected cells. The selective inhibition of ST suggested the newly designed monofunctional DKAs bind the IN-DNA acceptor site without affecting the DNA donor site.

  DOI：

  10.1021/jm8001422
• 作为产物：
  描述：

  2-氨基-5-氯苯甲酸甲酯 在 potassium tert-butylate 、 双(2-二苯基磷苯基)醚 、 copper(l) chloride 作用下， 以 甲苯 为溶剂， 反应 2.34h， 生成 3-acetyl-6-chloroquinolin-4(1H)-one
  参考文献：
  名称：

  铜催化的2-氨基苯甲酸酯在β-取代的α，β-不饱和酮上的铜催化Aza-Michael加成反应：一锅法合成3-羰基-2-取代的喹啉4（1 H）-ones

  摘要：

  我们提出了一种新的，直接的一锅法，用于通过高效的Cu催化2-氨基苯甲酸酯向β-取代的α，β-不饱和酮/环化/温和的2-氨基苯甲酸酯加成反应来合成3-羰基-4-喹诺酮衍生物氧化反应。在温和的反应条件下，以较短的反应时间，由现成的化学物质制备了种类繁多的新型多功能3-羰基-喹啉-4（1 H）-酮，可产生良好至极好的收率（高达99％）。

  DOI：

  10.1021/acs.joc.7b03162

文献信息

• Mapata; Desai, Journal of the Indian Chemical Society, 1954, vol. 31, p. 951,955
  作者：Mapata、Desai

  DOI：——

  日期：——
• Novel Quinolinonyl Diketo Acid Derivatives as HIV-1 Integrase Inhibitors: Design, Synthesis, and Biological Activities
  作者：Roberto Di Santo、Roberta Costi、Alessandra Roux、Gaetano Miele、Giuliana Cuzzucoli Crucitti、Alberto Iacovo、Federica Rosi、Antonio Lavecchia、Luciana Marinelli、Carmen Di Giovanni、Ettore Novellino、Lucia Palmisano、Mauro Andreotti、Roberta Amici、Clementina Maria Galluzzo、Lucia Nencioni、Anna Teresa Palamara、Yves Pommier、Christophe Marchand

  DOI：10.1021/jm8001422

  日期：2008.8.1

  Novel quinolinonyl diketo acids were designed to obtain integrase (IN) inhibitors selectively active against the strand transfer (ST) step of the HIV integration process. Those new compounds are characterized by a single aryl diketo acid (DKA) chain in comparison to 4, a bifunctional diketo acid reported by our group as an anti-IN agent highly potent against both the 3'-processing and ST steps. Compound 6d was the most potent derivative in IN enzyme assays, while 6i showed the highest potency against HIV-1 in acutely infected cells. The selective inhibition of ST suggested the newly designed monofunctional DKAs bind the IN-DNA acceptor site without affecting the DNA donor site.
• Copper-Catalyzed Aza-Michael Addition of 2-Aminobenzoate to β-Substituted α,β-Unsaturated Ketones: One-Pot Synthesis of 3-Carbonyl-2-Substituted Quinolin-4(1<i>H</i>)-ones
  作者：Seongil Kang、Subin Park、Kyung-su Kim、Changsik Song、Yunmi Lee

  DOI：10.1021/acs.joc.7b03162

  日期：2018.3.2

  We present a new and straightforward one-pot process for the synthesis of 3-carbonyl-4-quinolone derivatives through highly efficient Cu-catalyzed aza-Michael addition of 2-aminobenzoates to β-substituted α,β-unsaturated ketones/cyclization/mild oxidation reactions. A broad range of new versatile 3-carbonyl-quinolin-4(1H)-ones is prepared from readily available chemicals under mild reaction conditions

  我们提出了一种新的，直接的一锅法，用于通过高效的Cu催化2-氨基苯甲酸酯向β-取代的α，β-不饱和酮/环化/温和的2-氨基苯甲酸酯加成反应来合成3-羰基-4-喹诺酮衍生物氧化反应。在温和的反应条件下，以较短的反应时间，由现成的化学物质制备了种类繁多的新型多功能3-羰基-喹啉-4（1 H）-酮，可产生良好至极好的收率（高达99％）。