1,4-dihydro-4-oxo-2-phenylquinoline-3-carboxylic acid ethyl ester | 79607-25-3

• 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: 1,4-dihydro-4-oxo-2-phenylquinoline-3-carboxylic acid ethyl ester
• 英文别名: ethyl 4-oxo-2-phenyl-1,4-dihydroquinoline-3-carboxylate；2-phenyl-3-ethoxycarbonyl-4(1H)-quinolone；ethyl 2-phenyl-4-quinolone-3-carboxylate；ethyl 4-oxo-2-phenyl-1H-quinoline-3-carboxylate
• CAS: 79607-25-3
• 化学式: C₁₈H₁₅NO₃
• 分子量: 293.322
• InChiKey: KAXJGTFTNGYKFK-UHFFFAOYSA-N

物化性质

• 沸点：
  453.1±45.0 °C(Predicted)
• 密度：
  1.240±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 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：
  4

反应信息

• 作为反应物：
  描述：

  1,4-dihydro-4-oxo-2-phenylquinoline-3-carboxylic acid ethyl ester 生成 2-苯基喹啉
  参考文献：
  名称：

  Niementowski, Chemische Berichte, 1905, vol. 38, p. 2045

  摘要：

  DOI：
• 作为产物：
  描述：

  4-ethoxycarbonyl-1,5-diphenyl-1H-pyrrole-2,3-dione 以 二苯醚 为溶剂， 反应 0.25h， 以91%的产率得到1,4-dihydro-4-oxo-2-phenylquinoline-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  A nitroketene to nitrile oxide transformation

  摘要：

  2,3-二氢吡咯-2,3-二酮1在热条件下排出CO，生成亚咪酰酮烯2，后者高效环化形成4-喹啉酮3；然而，类似的硝基（亚咪酰）酮烯5则排出CO2，并重排生成3-羟肟基-3H-吲哚9，可能是通过亚咪酰腈氧化物7实现的。

  DOI：

  10.1039/c39920000485

文献信息

• Cascade Knoevenagel and aza-Wittig reactions for the synthesis of substituted quinolines and quinolin-4-ols
  作者：Xiaofeng Zhang、Xiaoming Ma、Weiqi Qiu、Jason Evans、Wei Zhang

  DOI：10.1039/c8gc03180k

  日期：——

  A [4 + 2] annulation involving cascade Knoevenagel, aza-Wittig and dehydrofluorination reactions is developed for the synthesis of substituted quinolin-4-ols including analogs bearing CF2H, CF3, and C2F5 groups. This simple and highly efficient method is also applicable for the synthesis of substituted quinolines. A number of reported biologically active compounds can be readily prepared by this one-pot

  开发了一种包括级联Knoevenagel，aza-Wittig和脱氟化氢反应的[4 + 2]环合反应，用于合成取代的喹啉-4-醇，包括带有CF 2 H，CF 3和C 2 F 5基团的类似物。这种简单而高效的方法也适用于取代喹啉的合成。通过一锅法合成可以容易地制备许多报道的生物活性化合物。新反应过程的绿色化学指标分析提供了令人满意的结果。
• Eco-friendly decarboxylative cyclization in water: practical access to the anti-malarial 4-quinolones
  作者：Yue Ma、Yongping Zhu、Dong Zhang、Yuqing Meng、Tian Tang、Kun Wang、Ji Ma、Jigang Wang、Peng Sun

  DOI：10.1039/c8gc03570a

  日期：——

  An eco-friendly decaboxylative cyclization in water has been developed to construct 4-quinolones from readily available isatoic anhydrides and 1,3-dicarbonyl compounds.

  已经开发出一种在水中进行的环化脱羧反应，用于从易得的异安酸酐和1,3-二羰基化合物构建4-喹啉酮。
• Reactions of N-Hydroxysuccinimide Esters of Anthranilic Acids with Anions of .BETA.-Keto Esters. A New Route to 4-Oxo-3-quinolinecarboxylic Acid Derivatives.
  作者：Christos MITSOS、Alexandros ZOGRAFOS、Olga IGGLESSI-MARKOPOULOU

  DOI：10.1248/cpb.48.211

  日期：——

  A new approach for the synthesis of 4-oxo-3-quinolinecarboxylic acid derivtives is described. This methodology involves the C-acylation of the anions of appropriate β-keto esters with novel N-hydroxysuccinimide esters of anthranilic acids. The intermediate C-acylation products 3 are spontaneously cyclized to afford 3-ethoxycarbonyl-4-oxoquinoline derivatives 4. The introduction of a variety of substituents at positins 1 and 2 of the quinoline ring is feasible with the selection of suitable anthranilic acids and β-keto esters. The structure of the obtained 2-substituted 3-ethoxycarbonyl-4-oxoquinolines was confirmed by IR and NMR spectral data.

  本文介绍了一种合成 4-氧代-3-喹啉羧酸衍生物的新方法。该方法包括将适当的 β-酮酯阴离子与新型 N-羟基琥珀酰亚胺蒽酸酯进行 C-酰化。中间的 C-酰化产物 3 自发环化生成 3-乙氧羰基-4-氧代喹啉衍生物 4。通过选择合适的蒽酸和 β-酮酯，可以在喹啉环的阳离子 1 和 2 上引入各种取代基。红外光谱和核磁共振光谱数据证实了所获得的 2-取代 3-乙氧羰基-4-氧代喹啉的结构。
• Substituted 2-phenyl-4-quinolone-3-carboxylic acid compounds and their use as antitumor agents
  申请人：Kuo Sheng-Chu

  公开号：US20050032832A1

  公开（公告）日：2005-02-10

  Substituted 2-phenyl-4-quinolone-3-carboxylic acid derivatives and their salts were synthesized. The results of preliminary screening revealed that these compounds are potent in killing solid tumor cancers.

  合成了2-苯基-4-喹啉酮-3-羧酸衍生物及其盐。初步筛选结果显示，这些化合物对杀灭实体肿瘤癌细胞具有很强的效果。
• 화합물, 이를 포함하는 유기 광전자 소자 및 표시장치
  申请人：SAMSUNG SDI CO., LTD. 삼성에스디아이 주식회사(119980018058) Corp. No ▼ 110111-0394174BRN ▼124-81-31282

  公开号：KR20160050361A

  公开（公告）日：2016-05-11

  하기 화학식 1로 표시되는 화합물, 이를 포함하는 유기 광전자 소자 및 상기 유기 광전자 소자를 포함하는 표시장치에 관한 것이다. [화학식 1] (상기 화학식 1에서, X 내지 X, L 내지 L, 및 R 내지 R의 정의는 명세서에 정의된 바와 같다.)

  这是关于标记为化学式1的化合物，包括含有它的有机光电器件以及包含该有机光电器件的显示装置。[化学式1]（在上述化学式1中，X至X，L至L，以及R至R的定义如规范所定义。）