benzyl 2,3-dioxo-2,3-dihydroindole-1-carboxylate | 115046-41-8

• 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
• 英文名称: benzyl 2,3-dioxo-2,3-dihydroindole-1-carboxylate
• 英文别名: 1-Benzyloxycarbonylisatin；N-benzyloxycarbonyl isatin；2,3-Dioxo-2,3-dihydro-indole-1-carboxylic acid benzyl ester；benzyl 2,3-dioxoindole-1-carboxylate
• CAS: 115046-41-8
• 化学式: C₁₆H₁₁NO₄
• 分子量: 281.268
• InChiKey: YDHPGKMAVWLLPZ-UHFFFAOYSA-N

物化性质

• 沸点：
  453.8±38.0 °C(Predicted)
• 密度：
  1.400±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzyl 2,3-dioxo-2,3-dihydroindole-1-carboxylate 在 盐酸 、 4-二甲氨基吡啶 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 83.0h， 生成 benzyl (2-(2-(cyanomethyl)-3,10-dioxo-1,4-oxazecan-2-yl)phenyl)carbamate
  参考文献：
  名称：

  Synthesis of Lactams by Isomerization of Oxindoles Substituted at C-3 by an ω-Amino Chain

  摘要：

  Oxindoles substituted at N-1 by electron-withdrawing groups and at C-3 by omega-amino chains of various lengths undergo mild and easy isomerization to new 5- to 12-membered lactams in good yields (3096%). As efficient asymmetric syntheses of diversely 3,3-disubstituted oxindoles are currently developed, this isomerization provides a new and valuable access to medium-sized lactams alpha-substituted with a quaternary asymmetric carbon bearing a 2-aminophenyl residue.

  DOI：

  10.1021/jo501978j
• 作为产物：
  描述：

  isatin sodium salt 、 氯甲酸苄酯 以 苯 为溶剂， 以82%的产率得到benzyl 2,3-dioxo-2,3-dihydroindole-1-carboxylate
  参考文献：
  名称：

  Black, David St.C.; Chaichit, Narongsak; Gatehouse, Bryan M., Australian Journal of Chemistry, 1987, vol. 40, # 10, p. 1745 - 1754

  摘要：

  DOI：

文献信息

• Synthesis of 3,3-dichloro-2-oxindoles from isatin-3-p-tosylhydrazones and (dichloroiodo)benzene
  作者：Charlotte Hepples、Graham K. Murphy

  DOI：10.1016/j.tetlet.2015.06.063

  日期：2015.8

  Lewis base-catalyzed chlorination reaction that employs the hypervalent chlorinating agent PhICl2. The discovery of p-tosylhydrazones as chlorination precursors has expanded the functional group tolerance of the chlorination reaction to now include carbamates, acetamides, and sulfonates. Additionally, this allowed us to circumvent the use of the diazo group in our chlorination reaction, and offers

  将一系列芳基和N-取代的靛红衍生物转化为相应的isatin -3-对甲苯磺酰hydr，然后将其进行路易斯碱催化的氯化反应，该反应采用高价氯化剂PhICl 2。对氯甲苯甲酰肼作为氯化前体的发现使氯化反应的官能团耐受性扩大到现在包括氨基甲酸酯，乙酰胺和磺酸盐。此外，这使我们能够避免在氯化反应中使用重氮基团，并为探索我们的两步脱氧二卤代反应提供了新途径。我们还公开了PhICl 2的使用 用于将亚磺酸盐氧化氯化为相应的磺酰氯。
• Organocatalytic Synthesis of Benzazetidines by Trapping Hemiaminals with Protecting Groups
  作者：Riccardo Salvio、Simone Placidi、Arianna Sinibaldi、Antonio Di Sabato、Dario C. Buscemi、Andrea Rossi、Achille Antenucci、Andrei Malkov、Marco Bella

  DOI：10.1021/acs.joc.9b01148

  日期：2019.6.7

  Benzazetidines are highly strained and inherently unstable heterocycles. There are only few methodologies for assembling these compounds. Here, a protocol is presented to trap an elusive cyclic, four-membered hemiaminal structure. This method affords several benzazetidines in moderate to good yields (up to 81%), and it uses inexpensive materials and does not require catalysts based on transition metals

  苯并氮杂环丁烷是高度应变的且固有地不稳定的杂环。组装这些化合物的方法很少。在这里，提出了一种协议来捕获一种难以捉摸的环状四元半胱氨酸结构。该方法以中等至良好的收率（高达81％）提供了几种苯并氮杂环丁烷，并且使用廉价的材料且不需要基于过渡金属的催化剂。根据密度泛函理论计算，这些苯扎氮啶体系的高环应变能约为32 kcal mol –1。该合成也可以以克规模应用，反应产率基本不变。
• Synthesis of spiro(indoline‐3,1′‐pyrazolo[1,2‐ <i>a</i> ]pyrazoles) by 1,3‐dipolar cycloadditions of isatin <i>N</i> , <i>N</i> ′‐cyclic azomethine imines with alkynes
  作者：Yang Shi、Gangqiang Wang、Zhiyu Chen、Minghu Wu、Jian Wang、Leslie Trigoura、Haibing Guo、Yalan Xing、Shaofa Sun

  DOI：10.1002/jhet.3908

  日期：2020.4

  1,3‐Dipolar cycloaddition of isatin N,N′‐cyclic azomethine imine catalyzed by CuCO3 has been developed. Structurally interesting heterocyclic spiro(indoline‐3,1′‐pyrazolo[1,2‐a]pyrazoles) have been synthesized as single regioisomers in good yields and high functional group compatibility.

  已经开发了由CuCO 3催化的1，3-偶极环加成的isatin N，N'-环偶氮甲亚胺。结构上有趣的杂环螺（吲哚啉-3,1'-吡唑并[1,2- a ]吡唑）已被合成为单一的区域异构体，具有良好的收率和较高的官能团相容性。
• Quinazolin-2-ones having a spirohydantoin ring. II. Synthesis of several spiro(imidazolidine-4,4'(1'H)-quinazoline)-2,2',5(3'H)-triones via 5-hydroxyhydantoin derivatives.
  作者：Masafumi YAMAGISHI、Yoshihisa YAMADA、Ken-ichi OZAKI、Junichi TANI、Mamoru SUZUKI

  DOI：10.1248/cpb.39.626

  日期：——

  Reaction of 1-ethoxycarbonylisatin (1b) with urea gave 5-(2-ethoxycarbonylaminophenyl)-5-hydroxyhydantoin (4b) in a good yield. Treatment of 4b with several amines directly gave the corresponding spiro[imidazolidine-4, 4'(1'H)-quinazoline]-2, 2', 5(3'H)-trione derivatives (7a-d) in moderate yields. 3-Unsubstituted and 3-methylspiroquinazolin-2-one derivatives 7a, b were also synthesized from 5-ethoxy and 5-ethylthiohydantoins 5a, d, which in turn were easily obtained by the reaction of either ethanol or ethylmercaptan with 4b in the presence of a catalytic amount of sulfuric acid.

  将 1-乙氧基羰基靛红 (1b) 与脲反应，得到 5-(2-乙氧基羰基氨基苯基)-5-羟基海因 (4b)，收率很高。用几种胺直接处理 4b，可得到相应的螺[咪唑烷-4，4'(1'H)-喹唑啉]-2，2'，5(3'H)-三酮衍生物（7a-d），收率中等。5-乙氧基和 5-乙硫基海因 5a, d 也可合成 3-未取代和 3-甲基螺喹唑啉-2-酮衍生物 7a, b，这些衍生物又可通过乙醇或乙硫醇与 4b 在一定量的硫酸催化下反应而轻松获得。
• Selective inhibitors of clinically important mutants of the EGFR tyrosine kinase
  申请人：CS PHARMATECH LIMITED

  公开号：US10435388B2

  公开（公告）日：2019-10-08

  The present invention provides compounds of Formula (I) or a subgeneric structure or species thereof or a pharmaceutically acceptable salt, ester, solvate, and/or prodrug thereof and methods and compositions for treating or ameliorating abnormal cell proliferative disorders, such as cancer, wherein A, R2, R3, R10, E1, E2, E3, Y, and Z are as defined herein.

  本发明提供了式(I)化合物或其亚属结构或种类或其药学上可接受的盐、酯、溶液剂和/或原药，以及用于治疗或改善异常细胞增殖性疾病（如癌症）的方法和组合物，其中A、R2、R3、R10、E1、E2、E3、Y和Z如本文所定义。