6-chloro-4-(2-chlorophenyl)quinolin-2(1H)-one | 579520-48-2

• 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: 6-chloro-4-(2-chlorophenyl)quinolin-2(1H)-one
• 英文别名: 6-chloro-4-(2-chlorophenyl)-1H-quinolin-2-one
• CAS: 579520-48-2
• 化学式: C₁₅H₉Cl₂NO
• 分子量: 290.149
• InChiKey: KAMBXYAMFJKAJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-氯-(N-Boc)苯胺 在 盐酸 、 水 、 叔丁基锂 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 28.52h， 生成 6-chloro-4-(2-chlorophenyl)quinolin-2(1H)-one
  参考文献：
  名称：

  Synthesis of Quinolin-2-one Alkaloid Derivatives and Their Inhibitory Activities against HIV-1 Reverse Transcriptase

  摘要：

  基于已确立的HIV-1非核苷类逆转录酶抑制剂（NNRTI）的共同药效团，首次合成了一系列喹啉-2-酮衍生物，并测定了它们对HIV-1逆转录酶（RT）的体外活性。其中一些化合物表现出对抗HIV-1 RT的活性。化合物4a2和4d2显示出抑制活性，其IC50值分别为0.21和0.15 mM，与依非韦伦相似，它们与RT的别构口袋残基的相互作用方式相似。

  DOI：

  10.3390/molecules16097649

文献信息

• 2-[3-(Phthalimidomethyl)-5-methyl-4H-1,2,4-triazol-4-yl]benzophenones
  申请人：The Upjohn Company

  公开号：US03993660A1

  公开（公告）日：1976-11-23

  A process to make 6-phenyl-4H-s-triazolo[4,3-a][1,4]-benzodiazepines by converting 2-[3-(hydroxymethyl)-4H-1,2,4-triazol-4-yl]benzophenones to 2-[3-[(phthalimido or methanesulfonyl)methyl]-4H-1,2,4-triazol-4-yl]benzophenones and converting these compounds to the highly active 6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepines useful as tranquilizers and sedatives.

  将2-[3-(羟甲基)-4H-1,2,4-三唑-4-基]苯酮转化为2-[3-[(邻苯二甲酰亚胺或甲磺酰基)甲基]-4H-1,2,4-三唑-4-基]苯酮，然后将这些化合物转化为作为镇静剂和催眠剂有用的高活性6-苯基-4H-s-三唑并[4,3-a][1,4]-苯二氮䓬。
• Lactamization of sp²C−H Bonds with CO₂: Transition-Metal-Free and Redox-Neutral
  作者：Zhen Zhang、Li-Li Liao、Si-Shun Yan、Lei Wang、Yun-Qi He、Jian-Heng Ye、Jing Li、Yong-Gang Zhi、Da-Gang Yu

  DOI：10.1002/anie.201602095

  日期：2016.6.13

  The first direct use of carbon dioxide in the lactamization of alkenyl and heteroaryl C−H bonds to synthesize important 2‐quinolinones and polyheterocycles in moderate to excellent yields is reported. Carbon dioxide, a nontoxic, inexpensive, and readily available greenhouse gas, acts as an ideal carbonyl source. Importantly, this transition‐metal‐free and redox‐neutral process is eco‐friendly and desirable

  据报道，在烯基和杂芳基CH键的内酰胺化中首次直接使用二氧化碳以中等至极好的收率合成重要的2-喹啉酮和多杂环化合物。二氧化碳是一种无毒，廉价且易于获得的温室气体，是理想的羰基来源。重要的是，这种无过渡金属和氧化还原中性的工艺对生态友好，是制药业的理想之选。此外，这些反应具有广泛的底物范围，良好的官能团耐受性，简便的可扩展性和易于产品衍生化的特点。
• Synthesis of Substituted Coumarins and 2-Quinolinones by Cycloisomerisation of (Hydroxy/aminophenyl)propargyl Alcohols
  作者：Maddi Sridhar Reddy、Nuligonda Thirupathi、Madala Hari Babu

  DOI：10.1002/ejoc.201200782

  日期：2012.10

  A new cycloisomerization strategy for the synthesis of coumarins and quinolinones is described. The addition of ethoxyacetylide to 2-hydroxyacetophenones directly resulted in 4-substituted coumarins by 6-endo-dig cycloisomerisation of the intermediate 3-ethoxy-1-(2-hydroxyphenyl)-2-propyn-1-ols. Under similar conditions, 2-aminoacetophenone produced 2-ethoxyquinoline, a masked quinolinone, which was

  描述了合成香豆素和喹啉酮的一种新的环异构化策略。通过中间体 3-乙氧基-1-(2-羟基苯基)-2-丙炔-1-醇的 6-endo-dig 环异构化，将乙氧基乙炔添加到 2-羟基苯乙酮中直接产生 4-取代香豆素。在类似条件下，2-氨基苯乙酮产生2-乙氧基喹啉，一种掩蔽的喹啉酮，通过酸处理转化为喹啉酮。N-保护的中间体 8 被分离并转化为喹啉酮 [使用 In(OTf)3 或 H2SO4] 或 3-iodo-2-quinolinone（使用 I2 和 H+）。
• Synthesis and in vitro anti-hepatitis B virus activities of 4-aryl-6-chloro-quinolin-2-one and 5-aryl-7-chloro-1,4-benzodiazepine derivatives
  作者：Pi Cheng、Quan Zhang、Yun-Bao Ma、Zhi-Yong Jiang、Xue-Mei Zhang、Feng-Xue Zhang、Ji-Jun Chen

  DOI：10.1016/j.bmcl.2008.05.065

  日期：2008.7

  A series of 4-aryl-6-chloro-quinolin-2-ones and 5-aryl-7-chloro-1,4-benzodiazepine were synthesized and assayed for their in vitro anti-hepatitis B virus activities and cytotoxicities for the first time. Some of the tested compounds were active against HBsAg and HBeAg secretion in Hep G2.2.15 cells. Compound 5c showed IC50 of 0.074 and 0.449 mM on HBsAg and HBeAg secretions, respectively, which were 10 times higher than that of its analog 4c and led to better selective index (SI) values (SI = 23.2 and 3.4, respectively). (c) 2008 Elsevier Ltd. All rights reserved.
• Lactamization of Alkenyl C-H Bonds to Generate 2-Quinolinones with Triphosgene
  作者：Zhen Zhang、Guizhi Du、Zixiao Wang

  DOI：10.3987/com-20-14232

  日期：——

  A simple and easy-going method is developed to synthesize the analogues of 2-quinolinones by using triphosgene (BTC) as the carbonyl source. In these reactions, both the toxic carbon monoxide (CO) and phosgene are avoided and the 2-quinolinones are obtained in moderate to good yields under mild conditions, all of which are anticipated to be meaningful in both industry and laboratory.