ethyl 6-chloro-4-(2-chlorophenyl)-1,2-dihydro-2-oxo-3-quinolinecarboxylate | 136280-96-1

• 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: ethyl 6-chloro-4-(2-chlorophenyl)-1,2-dihydro-2-oxo-3-quinolinecarboxylate
• 英文别名: ethyl 6-chloro-4-(2-chlorophenyl)-2-oxo-1,2-dihydroquinoline-3-carboxylate；ethyl 6-chloro-4-(2-chlorophenyl)-1,2-dihydro-2-oxoquinoline-3-carboxylate；6-chloro-(2'-chlorophenyl)-2-quinolinone-3-carboxylic acid ethyl ester；ethyl 6-chloro-4-(2-chlorophenyl)-2-oxo-1H-quinoline-3-carboxylate
• CAS: 136280-96-1
• 化学式: C₁₈H₁₃Cl₂NO₃
• 分子量: 362.212
• InChiKey: SWYGIPJLKMEMBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 6-chloro-4-(2-chlorophenyl)-1,2-dihydro-2-oxo-3-quinolinecarboxylate 在 sodium methylate 、 三氯氧磷 作用下， 反应 8.0h， 生成 methyl 6-chloro-4-(2-chlorophenyl)-2-methoxy-3-quinolinecarboxylate
  参考文献：
  名称：

  香豆素和2-喹诺酮的3-脲基衍生物的合成作为有效的酰基辅酶A：胆固醇酰基转移酶抑制剂。

  摘要：

  合成了4-苯基香豆素和4-苯基-2-喹诺酮的新型3-脲基衍生物，并评估了其酰基辅酶A：胆固醇酰基转移酶（ACAT）的抑制活性。这些衍生物以10（-8）至10（-9）M的水平抑制大鼠肠道ACAT的IC50值，并发现当以膳食混合物的形式给予胆固醇喂养的大鼠时，血浆中的胆固醇水平正常化。

  DOI：

  10.1248/cpb.43.616
• 作为产物：
  描述：

  丙二酸二乙酯 在 ammonium peroxydisulfate 、 rose bengal 、 铁粉 、 碳酸氢钠 、 溶剂黄146 作用下， 以 甲醇 、 水 为溶剂， 反应 50.0h， 生成 ethyl 6-chloro-4-(2-chlorophenyl)-1,2-dihydro-2-oxo-3-quinolinecarboxylate
  参考文献：
  名称：

  Visible Light‐Induced Metal‐free Arylation of Coumarin‐3‐carboxylates with Arylboronic Acids

  摘要：

  The present work represents a novel methodology for the selective arylation of coumarin‐3‐carboxylates with arylboronic acids via a photochemical route, marking the first‐ever attempt for the direct alkenyl C−H arylation using rose bengal as a photocatalyst, which is a readily available and cost‐effective alternative to transition metal catalysis. The reaction proceeds smoothly in MeOH/H₂O solvent media in the presence of radical initiator affording the arylated products in good yields (60–80 %). The reaction parameters such as visible light, radical initiator, oxidant, anhydrous solvent, and inert atmosphere play a crucial role for the success of this methodology. The substituents present on the substrate show a significant effect on the conversion. This study provides a valuable contribution to the field of organic synthesis offering a new and efficient approach to the arylation of coumarin‐3‐carboxylic acid esters with a broad substrate scope and high functional group tolerance. It is a versatile method and provides a direct access to biologically relevant 4‐arylcoumarin‐3‐carboxylates.

  DOI：

  10.1002/asia.202400042

文献信息

• Quinoline derivatives, their production and use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US05223513A1

  公开（公告）日：1993-06-29

  A quinoline derivative of the formula (I): ##STR1## wherein each phenyl ring of A, B and C can have one or more substituents, X is ##STR2## (R.sup.1 is a hydrogen atom or a lower alkyl group) or ##STR3## (R.sup.2 is a lower alkyl group or a lower alkoxy group), and n is 0 or 1, or its salt, which possesses an inhibitory action against acyl-CoA: cholesterol acyltransferase.

  式(I)的喹啉衍生物：##STR1##其中A、B和C的每个苯环可以有一个或多个取代基，X是##STR2##（R1是一个氢原子或低级烷基组）或##STR3##（R2是一个低级烷基组或低级烷氧基组），n是0或1，或其盐，具有抑制酰基辅酶A:胆固醇酰基转移酶的作用。
• A convenient and efficient C–OH bond activation, PdCl₂(PPh₃)₂catalyzed, C–C bond formation of tautomerizable quinolinones with the aid of BOP reagent and boronic acids
  作者：Yadavalli Suneel Kumar、C. Dasaradhan、Kamalakannan Prabakaran、Fazlur-Rahman Nawaz Khan、Euh Duck Jeong、Eun Hyuk Chung、Hyun Gyu Kim Hyun Gyu Kim

  DOI：10.1039/c4ra05161k

  日期：——

  C–C bond formation of tautomerizable quinolinones. C–OH bond activation using BOP reagent and boronic acids.

  酮互变异构的喹啉酮的C-C键形成。使用BOP试剂和硼酸对C-OH键进行活化。
• Quinoline-3-carboxylates as potential antibacterial agents
  作者：V. Krishnakumar、Fazlur-Rahman Nawaz Khan、Badal Kumar Mandal、Sukanya Mitta、Ramu Dhasamandha、Vindhya Nanu Govindan

  DOI：10.1007/s11164-012-0505-1

  日期：2012.10

  The ethyl-2-chloroquinoline-3-carboxylates, 4, were achieved from o-aminobenzophenones in two steps. i.e. initially, the ethyl-2-oxoquinoline-3-carboxylates, 3, were obtained by base-catalyzed Friedlander condensations of o-aminobenzophenones, 1, and diethylmalonate, 2. The 2-chloroquinoline-3-carboxylates, 4, were then obtained by the reaction with POCl3 in good yields. The chemical structures were confirmed by FTIR, mass and 1H-NMR spectroscopic techniques. All the synthesized compounds were tested for their in vitro antibacterial activity against Bacillus subtilis and Vibrio cholera and found to possess moderate activity.

  邻氨基二苯甲酮通过两个步骤获得 2-氯喹啉-3-羧酸乙酯 4，即首先通过邻氨基二苯甲酮 1 和二乙基丙二酸二酯在碱催化下的弗里德兰德缩合反应获得 2-氧代喹啉-3-羧酸乙酯 3，然后通过与 POCl3 反应以良好的产率获得 2-氯喹啉-3-羧酸乙酯 4。傅立叶变换红外光谱、质谱和 1H-NMR 光谱技术证实了这些化合物的化学结构。对所有合成化合物进行了体外抗菌测试，发现它们对枯草杆菌和霍乱弧菌具有中等程度的抗菌活性。
• Syntheses of fused heterocyclic compounds and their inhibitory activities for squalene synthase
  作者：Takashi Miki、Masakuni Kori、Akira Fujishima、Hiroshi Mabuchi、Ryu-ichi Tozawa、Masahira Nakamura、Yasuo Sugiyama、Hidefumi Yukimasa

  DOI：10.1016/s0968-0896(01)00289-9

  日期：2002.2

  A variety of fused heterocyclic compounds (2-11) were synthesized as a modification of the lead compound 1a and evaluated for their inhibition of squalene synthase. 4,1-Benzothiazepine derivative 2, 1,4-benzodiazepine derivative 6, 1,3-benzodiazepine derivative 7, 1-benzazepine derivative 9, and 4,1-benzoxazocine derivative 10 potently inhibited squalene synthase activity, whereas the 4,1-benzoxazepine

  合成了多种稠合的杂环化合物（2-11），作为先导化合物1a的修饰，并评估了它们对角鲨烯合酶的抑制作用。4,1-苯并噻氮平衍生物2、1,4-苯并二氮杂卓衍生物6、1,3-苯并二氮杂卓衍生物7、1-苯并ze庚因衍生物9和4,1-苯并恶唑啉衍生物10有效抑制角鲨烯合酶活性，而4,1-苯并a氮平衍生物1是最有效的抑制剂。发现4，1-苯并噻氮平S-氧化物衍生物4，1,4-苯并二氮杂卓衍生物5，1,3,4-苯并三氮杂卓衍生物8和1,2,3,4-四氢喹啉衍生物11具有弱活性。这些化合物（1a，2、4、5、7和10）的X射线结构比较表明，5-（或6）-苯基的取向对活性很重要。
• US5223513A
  申请人：——

  公开号：US5223513A

  公开（公告）日：1993-06-29