1-(prop-2-yn-1-yl)quinolin-2(1H)-one | 35227-94-2

• 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: 1-(prop-2-yn-1-yl)quinolin-2(1H)-one
• 英文别名: 1-(2-Propinyl)-carbostyril；N-Propargylcarbostyril；1-prop-2-ynyl-1H-quinolin-2-one；1-(2-propynyl)-2(1H)quinolinone；1-prop-2-ynylquinolin-2-one
• CAS: 35227-94-2
• 化学式: C₁₂H₉NO
• 分子量: 183.21
• InChiKey: AYYNRDDFCUVLNV-UHFFFAOYSA-N

物化性质

• 熔点：
  137-139 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  288.0±39.0 °C(Predicted)
• 密度：
  1.182±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(prop-2-yn-1-yl)quinolin-2(1H)-one 在 甲醇 、 samarium diiodide 、 水 作用下， 以 四氢呋喃 为溶剂， 以60%的产率得到3,4-dihydro-1-(2-propynyl)-2(1H)-quinolinone
  参考文献：
  名称：

  SmI2/H2O/MeOH 系统促进喹啉酮的选择性还原

  摘要：

  首次报道了由 SmI 2 /H 2 O/MeOH 体系促进 quinolin-2(1 H )-ones的选择性还原。该反应在温和条件下以一锅法有效地进行，得到 3,4-二氢喹啉-2(1 H )-酮，产率从良好到优异。

  DOI：

  10.1021/acs.joc.2c00389
• 作为产物：
  描述：

  肉桂酰氯 在 aluminum (III) chloride 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 氯苯 为溶剂， 反应 4.0h， 生成 1-(prop-2-yn-1-yl)quinolin-2(1H)-one
  参考文献：
  名称：

  SmI2/H2O/MeOH 系统促进喹啉酮的选择性还原

  摘要：

  首次报道了由 SmI 2 /H 2 O/MeOH 体系促进 quinolin-2(1 H )-ones的选择性还原。该反应在温和条件下以一锅法有效地进行，得到 3,4-二氢喹啉-2(1 H )-酮，产率从良好到优异。

  DOI：

  10.1021/acs.joc.2c00389

文献信息

• Triazolo(4,3-A)(1,4)benzodiazepines and thieno
  申请人：Hoffmann-La Roche Inc.

  公开号：US04959361A1

  公开（公告）日：1990-09-25

  The invention relates to compounds of the formula ##STR1## wherein X is --CH.dbd.CH-- or S; R.sub.1 is lower alkyl, lower alkoxy or trifluoromethyl; R.sub.2 is hydrogen, lower alkyl, lower alkoxy, hydroxy or alkanoyloxy; R.sub.3 and R.sub.4, independently, are hydrogen, chlorine, fluorine, lower alkyl or lower alkoxy; s is an integer from 0 to 1, provided that when s is 1, R.sub.2 cannot be hydroxy, lower alkoxy or alkanoyloxy; R.sub.5 is a radical of the formula R.sub.6 --(CH.sub.2).sub.n -- or R.sub.7 --O--(CH.sub.2).sub.m -- wherein R.sub.6 and R.sub.7 are aryl or a heterocyclic radical, n is an integer of from 0 to 2 and m is an integer of from 1 to 2, provided that, when n is 0, R.sub.6 must be attached through a carbon to carbon bond, and provided that R.sub.7 is always attached through a carbon to oxygen bond, and, when at least one asymmetric carbon is present, its enantiomers and racemates, and pharmaceutically acceptable acid addition salts thereof. The compounds of formula I exhibit activity as platelet activating factor (PAF) antagonists and are, therefore, useful in disease states characterized by excess platelet activating factor or for the prevention and treatment of cardiovascular diseases, pulmonary diseases, immunological disorders, inflammatory diseases, dermatological disorders, shock or transplant rejection.

  本发明涉及通式##STR1##的化合物，其中X为--CH=CH--或S；R1为低级烷基、低级烷氧基或三氟甲基；R2为氢、低级烷基、低级烷氧基、羟基或烷酰氧基；R3和R4各自独立地为氢、氯、氟、低级烷基或低级烷氧基；s为0至1的整数，但当s为1时，R2不能为羟基、低级烷氧基或烷酰氧基；R5为通式R6--(CH2)n--或R7--O--( )m--的基团，其中R6和R7为芳基或杂环基团，n为0至2的整数，m为1至2的整数，但当n为0时，R6必须通过碳-碳键连接，且R7始终通过碳-氧键连接，当存在至少一个不对称碳时，包括其对映体和外消旋体，以及药学上可接受的酸加成盐。通式I的化合物表现出作为血小板活化因子（PAF）拮抗剂的活性，因此可用于治疗以过量血小板活化因子为特征的疾病状态，或用于预防和治疗心血管疾病、肺部疾病、免疫紊乱、炎症性疾病、皮肤病、休克或移植排斥反应。
• One-pot synthesis of cyclobutenecarboxylate derivatives via olefinic C-F bond functionalization of gem-difluoroalkenes
  作者：Xiao Hu、Yang Li、Hao Guo

  DOI：10.1016/j.tetlet.2022.153673

  日期：2022.3

  A one-pot approach which provides a series of cyclobutenecarboxylates in moderate to excellent yields has been developed. This strategy involves visible light-induced [2+2]-photocycloaddition of quinolinones with 1-bromo-1-trifluoromethylethene, followed by tandem sodium alkoxide-promoted elimination, nucleophilic vinylic substitution and hydrolysis. The in-situ generated gem-difluoroalkene is the

  已经开发了一种以中等至极好的产率提供一系列环丁烯羧酸盐的一锅法。该策略涉及可见光诱导的喹啉酮与 1-溴-1-三氟甲基乙烯的 [2+2]-光环加成，然后是串联醇钠促进的消除、亲核乙烯基取代和水解。原位生成的宝石-二氟烯烃是实现这一转变的关键中间体。优异的官能团相容性和高区域选择性使该方法具有灵活性和实用性。值得注意的是，在该协议中可以很容易地获得环丁烯羧酸，进一步展示了该策略的合成潜力。
• Triazolobenzo- and triazolothienodiazepines as potent antagonists of platelet activating factor
  作者：Armin Walser、Thomas Flynn、Carl Mason、Herman Crowley、Catherine Maresca、Bob Yaremko、Margaret O'Donnell

  DOI：10.1021/jm00107a048

  日期：1991.3

  A series of [1,2,4]triazolo[4,3-alpha][1,4]benzodiazepines bearing an ethynyl functionality at the 8-position and the isosteric thieno[3,2-f][1,2,4]triazolo[4,3-alpha][1,4]diazepines were prepared and evaluated as antagonists of platelet activating factor. The effects of substitution were explored in in vitro and in vivo test systems designed to measured PAF-antagonistic activity. Results are discussed and compared with previously published data. Many of the compounds had activity superior to WEB 2086, compound 1. In general, the thieno analogues exhibited better oral activity than the corresponding benzodiazepines. The duration of activity upon oral administration was modulated by the substitution on the acetylenic side chain. Compounds 71 and 81 were selected for further pharmacological evaluation as a result of their good oral potency and exceptionally long duration of action.
• WALSER, ARMIN;FLYNN, THOMAS;MASON, CARL;CROWLEY, HERMAN;MARESCA, CATHERIN+, J. MED. CHEM., 34,(1991) N, C. 1209-1221
  作者：WALSER, ARMIN、FLYNN, THOMAS、MASON, CARL、CROWLEY, HERMAN、MARESCA, CATHERIN+

  DOI：——

  日期：——
• Triazolodiazepine derivatives
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP0320992B1

  公开（公告）日：1994-07-27