spiro[indole-3,2'-oxiran]-3'-benzoyl-2(1H)-one | 16120-49-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: spiro[indole-3,2'-oxiran]-3'-benzoyl-2(1H)-one
• 英文别名: 3'-benzoylspiro[2-oxoindoline-3,2'-oxirane]；3'-benzoylspiro[indoline-3,2'-oxiran]-2-one；3'-benzoyl-1H-spiro[indole-3,2'-oxiran]-2-one；3'-benzoyl-spiro[indolin-3,2'-oxiran]-2-one；3'-Benzoyl-spiro[indolin-3,2'-oxiran]-2-on；3'-benzoylspiro[1H-indole-3,2'-oxirane]-2-one
• CAS: 16120-49-3
• 化学式: C₁₆H₁₁NO₃
• 分子量: 265.268
• InChiKey: BOOIGQMUXQLUDZ-UHFFFAOYSA-N

物化性质

• 沸点：
  522.9±50.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  58.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  spiro[indole-3,2'-oxiran]-3'-benzoyl-2(1H)-one 在 sodium hydroxide 、 乙醇 、 水 作用下， 生成 2-苄基-1H-吲哚-3-羧酸
  参考文献：
  名称：

  328.淫羊line类。第一部分。表皮二酮合成的各种方法的试验

  摘要：

  DOI：

  10.1039/jr9340001508
• 作为产物：
  描述：

  3-benzoylmethylidene-2-oxindole 在 双氧水 作用下， 生成 spiro[indole-3,2'-oxiran]-3'-benzoyl-2(1H)-one
  参考文献：
  名称：

  Ultrasound promoted greener synthesis of spiro[indole-3,5′-[1,3]oxathiolanes in water

  摘要：

  An aqueous mediated novel synthesis of substituted 2'amino-4'benzoyl-2'-methyl spiro[indole 3,5'-[1,3]oxathiolane]-2(1H)-ones (2a-f) was carried out from the reaction of spiro [indole-3,2'-oxiranes] (1a-f) with thioacetamide in the presence of LiBr as catalyst. The reaction was carried out under both microwaves and sonication and results were also compared with conventional method. in general, improvement in rate and yields observed when reaction was carried out under sonication as compared to microwave irradiation and conventional method. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ultsonch.2009.08.003

文献信息

• Polyfunctional 4-quinolinones. Synthesis of 2-substituted 3-hydroxy-4-oxo-1,4-dihydroquinolines
  作者：María S. Shmidt、Isabel A. Perillo、Alicia Camelli、María A. Fernández、María M. Blanco

  DOI：10.1016/j.tetlet.2016.01.077

  日期：2016.3

  We present here two new methods based on rearrangement reactions to obtain novel 2-substituted 3-hydroxy-4-oxo-1,4-dihydroquinolines, an important family of heterocycles with potential applications. Alkyl 3-hydroxy-4-oxo-1,4-dihydroquinoline-2-carboxylates were obtained by alkoxide promoted rearrangement of alkyl isatinacetates. A second synthetic route involves the alkoxide promoted reaction of both

  我们在此介绍两种基于重排反应的新方法，以获得新颖的2-取代的3-羟基-4-氧代-1,4-二氢喹啉，具有重要应用前景的重要的杂环族。通过醇盐促进烷基异氰酸酯乙酸酯的重排获得3-羟基-4-氧代-1,4-二氢喹啉-2-羧酸烷基酯。第二种合成途径涉及伊斯丁和N-甲基伊斯丁两者的醇盐促进的反应，以及具有酸性亚甲基的烷基化剂。该反应导致通过Darzens的缩合形成螺氧基环氧吲哚。当使用苯甲酰溴时，将最初获得的苯甲酰基取代的螺氧基环氧吲哚以良好或优异的收率平稳地转化为相应的2-苯甲酰基-3-羟基-4-喹啉酮。
• Simple and Efficient Microwave Assisted N-Alkylation of Isatin
  作者：María Shmidt、Ana Reverdito、Lautaro Kremenchuzky、Isabel Perillo、María Blanco

  DOI：10.3390/molecules13040831

  日期：——

  We present herein the results of microwave promoted N-alkylations of isatin (1)with different alkyl, benzyl and functionalized alkyl halides. Reactions were carried out under different conditions, always employing methodologies compatible with MW assisted chemistry. Generation of isatin anion employing diverse bases and solvents or using the preformed isatin sodium salt was tested. The best results

  我们在本文中介绍了微波促进靛红 (1) 与不同烷基、苄基和官能化烷基卤化物的 N-烷基化的结果。反应在不同条件下进行，始终采用与 MW 辅助化学相容的方法。测试了使用不同碱和溶剂或使用预先形成的靛红钠盐生成靛红阴离子。使用 K(2)CO(3) 或 Cs(2)CO(3) 和几滴 N，N-二甲基甲酰胺或 N-甲基-2-吡咯烷酮取得了最好的结果。与使用常规加热进行的那些反应相比，这些反应具有显着的优势。
• Facile synthesis of functionalized spiro[indoline-3,2'-oxiran]-2-ones by Darzens reaction
  作者：Qin Fu、Chao-Guo Yan

  DOI：10.3762/bjoc.9.105

  日期：——

  A series of functionalized spiro[indoline-3,2'-oxiran]-2-ones was efficiently synthesized by Darzens reaction of phenacyl bromides with isatins both with N-alkyl groups and without N-substituent in the presence of potassium carbonate as a base catalyst. When two equivalents phenacyl bromides were used in the reaction, the N-substitution reaction of isatin also finished with the formation of spiro-oxirane-oxindoles.

  一系列功能化的螺环[吲哚啉-3,2'-环氧]-2-酮通过在钾碳酸盐存在下的苯乙酰溴与带有和不带有N-烷基基团的吲哚啉进行Darzens反应而高效合成。当在反应中使用两当量苯乙酰溴时，也完成了吲哚啉的N-取代反应，形成螺环氧环氧吲哚酮。
• Reaction of isatin with alkylating agents with acidic methylenes
  作者：María S. Shmidt、Isabel A. Perillo、Mercedes González、María M. Blanco

  DOI：10.1016/j.tetlet.2012.03.010

  日期：2012.5

  The reaction of isatin (1) with different alkyl halides 2 and alkaline carbonates in aprotic polar solvents leads mainly to N-alkyl derivatives 3. The use of alkylating agents that have acidic methylenes leads to competitive formation of the corresponding epoxide 5. The formation of 5 is favored by low-polarity solvents at low temperatures and strong bases. Epoxides 5c, d obtained using NaEtOH/EtOH at 0-5 degrees C are transformed into the corresponding 4-quinolinones 6 at higher temperatures. The use of Ag2CO3 allows obtaining compounds 3 as major products, along with varying amounts of labile O-alkyl derivatives 4 and dimerization products. (C) 2012 Elsevier Ltd. All rights reserved.
• BLACK D. S. C.; WONG L. C. H., J. CHEM. SOC. CHEM. COMMUN., 1980, NO 4, 200
  作者：BLACK D. S. C.、 WONG L. C. H.

  DOI：——

  日期：——