1-(丙-2-炔-1-基)二氢吲哚-2-酮 | 37994-11-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 1-(丙-2-炔-1-基)二氢吲哚-2-酮
• 英文名称: 1-Prop-2-ynyl-1,3-dihydroindol-2-one
• 英文别名: 1-Propinylindolin-2-on；1-prop-2-ynyl-1,3-dihydro-indol-2-one；N-Propargyl-2-indolinon；1-(Prop-2-yn-1-yl)indolin-2-one；1-prop-2-ynyl-3H-indol-2-one
• CAS: 37994-11-9
• 化学式: C₁₁H₉NO
• 分子量: 171.199
• InChiKey: FWTULBPAQCKTLY-UHFFFAOYSA-N

物化性质

• 熔点：
  101-103 °C(Solv: ethanol (64-17-5))
• 沸点：
  377.2±42.0 °C(Predicted)
• 密度：
  1.189±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 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-(丙-2-炔-1-基)二氢吲哚-2-酮 在 四丁基溴化铵 、 四丁基硫酸氢铵 、 rongalite 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  面向螺菌毒素的多样性导向方法：绿色试剂“荣格”的应用

  摘要：

  通过Diels-Alder（DA）反应已经组装了一系列功能化的螺并吲哚衍生物。在这里，使用了钙铝矾石来生成关键的磺胺基砌块，它们是DA化学中有用的潜在二烯等效物。此处使用的二溴中间体是通过使1,2,4,5-四（溴甲基）苯与受保护的羟吲哚衍生物在操作简单的反应条件下反应制得的。在我们的研究中，我们避免了各种中间体的分离，从而降低了成本和与整个过程相关的工作量。

  DOI：

  10.1016/j.tetlet.2015.04.095
• 作为产物：
  描述：

  N-tert-butoxycarbonyl-N-(prop-2-ynyl)aniline 在 Rh₂(CF₃CONH)₄ 盐酸 、 silica gel 作用下， 以 四氢呋喃 、 乙酸乙酯 、 苯 为溶剂， 反应 35.0h， 生成 1-(丙-2-炔-1-基)二氢吲哚-2-酮
  参考文献：
  名称：

  Ligand Effects in the Rhodium(II)-Catalyzed Reactions of .alpha.-Diazoamides. Oxindole Formation is Promoted by the Use of Rhodium(II) Perfluorocarboxamide Catalysts

  摘要：

  An improved procedure for the preparation of ethyl 2-diazomalonyl chloride ws developed which involves the reaction of ethyl diazoacetate with triphosgene. Using this diazo acid chloride, it was possible to prepare a variety of diazoamides from substituted amines. The rhodium(II)-catalyzed decomposition of these diazoamides was studied in order to probe the chemoselectivity of the carbenoid intermediates in intramolecular insertion reactions. Rhodium(II) acetate decomposition of N-benzyl-2-diazo-N-phenylmalonamic acid ethyl ester resulted in intramolecular C-H insertion to give ethyl 1,4-diphenyl-2-oxoazetidine-3-carboxylate. By changing the catalyst ligand to trifluoroacetamide, beta-lactam formation was completely suppressed in favor of the aromatic C-H insertion which produces an oxindole as the only detectable product. The competition between aliphatic and aromatic carbon-hydrogen insertion of 2-diazo-N-phenylmalonamic acid ethyl ester provides another example of ligand effectiveness in controlling chemoselectivity in dirhodium(II)-catalyzed metal carbene reactions. Thus, treatment of the N-isobutyldiazoanilide with rhodium(II) acetate results in exclusive aliphatic C-H insertion giving 4,4-dimethyl-2-oxo-1-phenylpyrrolidine-3-carboxylic acid ethyl ester, while the perfluorobutyramide ligand promotes oxidinole formation by aromatic C-H insertion. Several other rhodium(II)-catalyzed reactions were studied and were found to be highly catalyst dependent, rhodium(II) perfluorocarboxamides promoting aromatic C-H insertion, and hence oxindole formation, over O-H insertion, cyclization onto adjacent triple bonds, or cyclization to generate 1,3-dipolar intermediates.

  DOI：

  10.1021/jo00088a028

文献信息

• Iron (II)-catalyzed diastereoselective cross-dehydrogenetive coupling of 2-methyl quinazolinones with indolin-2-ones
  作者：Bhanwar Kumar Malviya、Ved Prakash Verma、Pinki B. Punjabi、Mukesh Kumar、Siddharth Sharma

  DOI：10.1016/j.tetlet.2021.153141

  日期：2021.6

  An efficient and highly diastereoselective synthesis of schizocommunin analogues has been achieved through an iron-catalyzed C(sp3)-H/C(sp3)-H cross-dehydrogenative coupling reaction between 2-methyl quinazolinones and indolin-2-ones. This method requires air (molecular oxygen) as an oxidant instead of chemical equivalent oxidising agents and prefunctionalized coupling partners. The developed schizocommunin

  通过铁催化的 C(sp 3 )-H/C(sp 3 )-H 2-甲基喹唑啉酮和 indolin-2-ones 之间的交叉脱氢偶联反应，实现了高效且高度非对映选择性合成裂殖菌素类似物。该方法需要空气（分子氧）作为氧化剂，而不是化学等价的氧化剂和预官能化的偶联伙伴。开发的裂殖菌素类似物以良好到极好的产率获得，并且可以耐受各种官能团。值得注意的是，裂殖菌素是一种具有广谱生物学特性的生物活性天然产物，其中抗癌特性就是其中之一。
• Acetylenchemie, 5. Mitt. PTC-Umsetzung von 4-Hydroxychinolin-2-on und Indolin-2-on mit 3-Bromprop-1-in
  作者：Johannes Reisch、Andreas Bathe

  DOI：10.1002/ardp.19873200812

  日期：——

  Die PTC‐Propinylierung der Titelverbindungen lieferte ein Oxazolochinolinon und fünf Propinylchinolinone sowie drei Propinylindolinone nebst einem Anthranilsäurepropinylester. Mögliche Reaktionswege werden diskutiert, die Ergebnisse mit den bislang bekannten Resultaten verglichen.

  标题化合物的PTC丙炔化产生一个恶唑并喹啉酮和五个丙炔基喹啉酮以及三个丙炔基吲哚啉酮以及一个丙炔基邻氨基苯甲酸酯。讨论了可能的反应途径，并将结果与​​目前已知的结果进行了比较。
• Dihydroindol-2-one derivatives as steroid hormone nuclear receptor modulators
  申请人：Grese Alan Timothy

  公开号：US20050054712A1

  公开（公告）日：2005-03-10

  he present invention relates to methods of treating pathological disorders susceptible to steroid hormone nuclear receptor modulation, particularly congestive heart failure, comprising administering to a patient in need thereof an effective amount of a compound of the formula: I or a pharmaceutically acceptable salt thereof. In addition, the present invention provides novel pharmaceutical compounds of Formula I, including the pharmaceutically acceptable salts thereof, as well as pharmaceutical compositions which comprise as an active ingredient a compound of Formula I.

  本发明涉及治疗易受类固醇激素核受体调节影响的病理障碍的方法，特别是充血性心力衰竭，包括向需要治疗的患者施用公式I的化合物或其药学上可接受的盐的有效量。此外，本发明提供了公式I的新型药物化合物，包括其药学上可接受的盐，以及包含公式I化合物作为活性成分的药物组合物。
• Iron-catalyzed selective construction of indole derivatives <i>via</i> oxidative C(sp³)–H functionalization of indolin-2-ones
  作者：Wei Chen、Lang-Qi Wen、Xiao-Bing Lu、Hui Zhou

  DOI：10.1039/d4ob00133h

  日期：2024.4.17

  manipulating the reaction conditions, particularly the choice of solvent, catalyst loading, and reaction sequence, a series of valuable indole derivatives, including isatins and symmetrical and nonsymmetrical isoindigos, were selectively synthesized in good to excellent yields. Furthermore, the gram-scale synthesis of compounds with biological anticancer activity under simple conditions highlights their great

  考虑到开发强大的催化剂的重要性和吲哚衍生物的药效团特征，我们描述了一种铁催化的吲哚啉-2-酮氧化C(sp 3 )–H功能化的可转换方法。使用FeCl 2作为催化剂、空气作为氧化剂、醇作为溶剂，选择性转化表现出优异的活性和化学选择性。通过控制反应条件，特别是溶剂的选择、催化剂负载量和反应顺序，选择性地合成了一系列有价值的吲哚衍生物，包括靛红以及对称和非对称异靛，收率良好至优异。此外，在简单条件下克级合成具有生物抗癌活性的化合物凸显了其在实际应用中的巨大潜力。
• 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.