2-fluorobenzofuro[3,2-c]quinolin-6(5H)-one | 124028-61-1

• 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: 2-fluorobenzofuro[3,2-c]quinolin-6(5H)-one
• 英文别名: 2-fluoro-5H-[1]benzofuro[3,2-c]quinolin-6-one
• CAS: 124028-61-1
• 化学式: C₁₅H₈FNO₂
• 分子量: 253.232
• InChiKey: GKFZYYRZAPLOMA-UHFFFAOYSA-N

物化性质

• 熔点：
  298-300 °C (decomp)
• 沸点：
  335.1±25.0 °C(Predicted)
• 密度：
  1.409±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  42.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-fluorobenzofuro[3,2-c]quinolin-6(5H)-one 在 五氯化磷 作用下， 以 三氯氧磷 为溶剂， 反应 2.0h， 以58%的产率得到6-Chloro-2-fluoro-[1]benzofuro[3,2-c]quinoline
  参考文献：
  名称：

  Yamaguchi, Seiji; Tsuzuki, Kunihiro; Kinoshita, Minoru, Journal of Heterocyclic Chemistry, 1989, vol. 26, p. 281 - 284

  摘要：

  DOI：
• 作为产物：
  描述：

  2-ethynyl-4-fluoroaniline 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 copper diacetate 、 三乙胺 、 silver carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 生成 2-fluorobenzofuro[3,2-c]quinolin-6(5H)-one
  参考文献：
  名称：

  Cs₂CO₃ as a source of carbonyl and ethereal oxygen in a Cu-catalysed cascade synthesis of benzofuran [3,2-c] quinolin-6[5-H]ones

  摘要：

  使用Cs2CO3作为羰基（CO）和乙醚氧的来源，同时构建C-C、C-O和C-N键，并利用Cu(OAc)2和Ag2CO3的组合进行苯并呋喃[3,2-c]喹啉-6(5H)-酮的级联合成。

  DOI：

  10.1039/c6ob01029f

文献信息

• Diastereoselective Synthesis of Dihydrobenzofuran Spirooxindoles and Their Transformation into Benzofuroquinolinones by Ring Expansion of Oxindole Core
  作者：Feng Wang、Jia-Qi Pan、Ruo-Xian Shi、Rui Ning、Mingshu Wu

  DOI：10.1021/acs.joc.3c02956

  日期：2024.4.5

  and efficient approach for the diastereoselective synthesis of dihydrobenzofuran spirooxindoles using 3-chlorooxindoles and imines is presented. This process involves a formal [4 + 1] annulation, yielding the product with excellent diastereoselectivity. Furthermore, a novel method for constructing benzofuroquinolinone scaffolds through the ring expansion of oxindoles has been established. This method

  提出了一种使用 3-氯吲哚和亚胺非对映选择性合成二氢苯并呋喃螺吲哚的温和有效的方法。该过程涉及正式的[4 + 1]环化，产生具有优异非对映选择性的产物。此外，还建立了一种通过羟吲哚扩环构建苯并呋喃喹啉酮支架的新方法。该方法涉及将内酰胺环扩展到喹啉酮骨架。此外，还提供了从3-氯吲哚和亚胺制备苯并呋喃喹啉酮支架的一锅法。
• Synthesis and cytotoxic activity evaluation of indolo-, pyrrolo-, and benzofuro-quinolin-2(1H)-ones and 6-anilinoindoloquinoline derivatives
  作者：Yeh-Long Chen、Chao-Ho Chung、I.-Li Chen、Po-Hsu Chen、Haw-Yaun Jeng

  DOI：10.1016/s0968-0896(02)00111-6

  日期：2002.8

  Certain indolo-, pyrrolo-, and benzofuro-quinolin-2(1H)-ones 4a,b, 6, 8, 16a-c and 6-anilinoindoloquinoline derivatives 10a,b, 11a,b, 12a,b have been synthesized and evaluated in vitro against a 3-cell lines panel consisting of MCF7 (Breast), NCI-H460 (Lung), and SF-268 (CNS). Those active compounds 4a,b, 6, 8, 10a,b, 11a,b, 12a,b were then evaluated in the full panel of 60 human tumor cell lines derived from nine cancer cell types. The results have shown that cytotoxicity decreases in the order of 6-anilinoindoloquinolines>indoloquinolin-2(1H)-ones>pyrroloquinolin-2(1H)-ones>benzofuroquinolin-2(1H)-ones. Among them, 1-[3-(11H-indolo[3,2-c]quinolin-6ylamino)phenyl]ethanone oxime hydrochloride (14a) and its 2-chloro derivative (11b) were most active, with mean GI(50) values of 1.70 and 1.35 muM, respectively. Both compounds 11a,b were also found to inhibit the growth of SNB-75 (CNS cancer cell) with a GI(50) value of less than 0.01 muM, and, therefore, were selected for further evaluation for in vivo antitumor activity. (C) 2002 Published by Elsevier Science Ltd.
• YAMAGUCHI, SEIJI;TSUZUKI, KUNIHIRO;KINOSHITA, MINORU;OH-HIRA, YUTAKA;KAWA+, J. HETEROCYCLIC CHEM., 26,(1989) N, C. 281-284
  作者：YAMAGUCHI, SEIJI、TSUZUKI, KUNIHIRO、KINOSHITA, MINORU、OH-HIRA, YUTAKA、KAWA+

  DOI：——

  日期：——
• Yamaguchi, Seiji; Tsuzuki, Kunihiro; Kinoshita, Minoru, Journal of Heterocyclic Chemistry, 1989, vol. 26, p. 281 - 284
  作者：Yamaguchi, Seiji、Tsuzuki, Kunihiro、Kinoshita, Minoru、Oh-hira, Yutaka、Kawase, Yoshiyuki

  DOI：——

  日期：——
• Cs₂CO₃ as a source of carbonyl and ethereal oxygen in a Cu-catalysed cascade synthesis of benzofuran [3,2-c] quinolin-6[5-H]ones
  作者：Wajid Ali、Anju Modi、Ahalya Behera、Prakash Ranjan Mohanta、Bhisma K. Patel

  DOI：10.1039/c6ob01029f

  日期：——

  Simultaneous construction of C–C, C–O, and C–N bonds utilizing Cs₂CO₃ as a source of carbonyl (CO) and ethereal oxygen and a cascade synthesis of benzofuro[3,2-c]quinolin-6(5H)-one are achieved using a combination of Cu(OAc)₂ and Ag₂CO₃.

  使用Cs2CO3作为羰基（CO）和乙醚氧的来源，同时构建C-C、C-O和C-N键，并利用Cu(OAc)2和Ag2CO3的组合进行苯并呋喃[3,2-c]喹啉-6(5H)-酮的级联合成。