(E)-tert-butyl 3-(2-ethoxy-2-oxoethylidene)-5-fluoro-2-oxoindoline-1-carboxylate | 1282523-38-9

• 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
• 英文名称: (E)-tert-butyl 3-(2-ethoxy-2-oxoethylidene)-5-fluoro-2-oxoindoline-1-carboxylate
• 英文别名: tert-butyl (3E)-3-(2-ethoxy-2-oxoethylidene)-5-fluoro-2-oxoindole-1-carboxylate
• CAS: 1282523-38-9
• 化学式: C₁₇H₁₈FNO₅
• 分子量: 335.332
• InChiKey: MECQGJVFLDRFOG-FMIVXFBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-2-[2-(tert-butyldimethylsilyloxy)cyclohex-2-enylidene]acetaldehyde 、 (E)-tert-butyl 3-(2-ethoxy-2-oxoethylidene)-5-fluoro-2-oxoindoline-1-carboxylate 在 (2S)-2-[二苯基[(三甲基硅酯)氧基]甲基]-吡咯烷 、 邻氟苯甲酸 作用下， 以 氘代氯仿 为溶剂， 反应 20.0h， 生成
  参考文献：
  名称：

  Cross-trienamines in Asymmetric Organocatalysis

  摘要：

  Cross-conjugated trienamines are introduced as a new concept in asymmetric organocatalysis. These intermediates are applied in highly enantioselective Diels-Alder and addition reactions, providing functionalized bicyclo[2.2.2]octane compounds and gamma'-addition products, respectively. The nature of the transformations and the intermediates involved are investigated by computational calculations and NMR analysis.

  DOI：

  10.1021/ja3068269
• 作为产物：
  描述：

  ethyl (E)-2-(5-fluoro-2-oxoindolin-3-ylidene)acetate 、 二碳酸二叔丁酯 在 4-二甲氨基吡啶 作用下， 以 乙腈 为溶剂， 生成 (E)-tert-butyl 3-(2-ethoxy-2-oxoethylidene)-5-fluoro-2-oxoindoline-1-carboxylate
  参考文献：
  名称：

  Cross-trienamines in Asymmetric Organocatalysis

  摘要：

  Cross-conjugated trienamines are introduced as a new concept in asymmetric organocatalysis. These intermediates are applied in highly enantioselective Diels-Alder and addition reactions, providing functionalized bicyclo[2.2.2]octane compounds and gamma'-addition products, respectively. The nature of the transformations and the intermediates involved are investigated by computational calculations and NMR analysis.

  DOI：

  10.1021/ja3068269

文献信息

• Design and synthesis of novel spirooxindole–indenoquinoxaline derivatives as novel tryptophanyl-tRNA synthetase inhibitors
  作者：Wen Ren、Qian Zhao、Meng Yu、Li Guo、Hongmei Chang、Xian Jiang、Youfu Luo、Wei Huang、Gu He

  DOI：10.1007/s11030-019-10011-2

  日期：2020.11

  Abstract In the current study, we used an integrated approach combining bioinformatics, rational drug design, one-pot synthesis, and biological experiments in vitro for the potential discovery of novel tryptophanyl-tRNA synthetase (TrpRS) inhibitors. Atom economic and diastereoselective syntheses were used to generate several Spirooxindole–indenoquinoxaline derivatives in situ from isatin and amino

  摘要 在当前的研究中，我们使用了整合的方法，结合了生物信息学，合理的药物设计，一锅合成和体外生物学实验，以发现新型色氨酸-tRNA合成酶（TrpRS）抑制剂。原子经济和立体选择性合成被用来生成几个Spirooxindole - indenoquinoxaline原位自靛红和氨基酸即衍生物。脯氨酸，苯甘氨酸和肌氨酸通过靶向偶氮甲亚胺的1，3-偶极环加成反应。这些化合物通过生化TrpRS抑制作用，使用体外实验测试各种革兰氏阳性和革兰氏阴性菌株以及弥漫性大B细胞淋巴瘤（DLBCL）细胞系来测定。化合物6e被发现是体外活性最高的化合物，分别针对hmTrpRS和ecTrpRS的IC 50值为225和74 nM。我们还发现针对金黄色葡萄球菌的测试的MIC 90值为4 µg / mL，针对DLBCL细胞系增殖的测试的IC 50值为2.9至4.8 µM。此外，化合物6e在诱导MRSA菌株中的细菌自溶方面非
• Enantioselective Organocatalytic Three-Component Vinylogous Michael/Aldol Tandem Reaction among 3-Alkylidene oxindoles, Methyleneindolinones, and Aldehydes
  作者：Jing-Xiang Xu、Yi-Syun Jiang、Chih-Hao Chen、Nadaraj Sathishkumar、Kai-Ti Chu、Ming-Hsi Chiang、Hsin-Tsung Chen、Jeng-Liang Han

  DOI：10.1021/acs.joc.1c02180

  日期：2022.1.7

  We reported a one-pot enantioselective three-component vinylogous Michael/aldol tandem reaction of prochiral 3-alkylidene oxindoles with methyleneindolinones and aldehydes using bifunctional organocatalysts. A variety of enantioenriched 3,3-disubstituted oxindoles 3 and spirolactones 4 were generated in moderate yields (up to 78%) with high stereoselectivities (up to >20:1 dr, >99% ee). Intriguingly

  我们报道了使用双功能有机催化剂的前手性 3-亚烷基羟吲哚与亚甲基吲哚啉酮和醛的一锅对映选择性三组分乙烯基 Michael/aldol 串联反应。多种对映体富集的 3,3-二取代羟吲哚3和螺内酯4以中等收率（高达 78%）和高立体选择性（高达 >20:1 dr，>99% ee）生成。有趣的是，我们观察到与多聚甲醛的羟醛反应生成带有羟甲基的3,3-二取代羟吲哚3 ，而与脂肪醛的反应生成螺内酯4。
• Trienamine catalysed unprecedented remote olefin <i>E</i>/<i>Z</i> isomerisation/[4 + 2]-cycloaddition reaction to access spirooxindole hexahydroindoles
  作者：Madavi S. Prasad、Murugesan Sivaprakash、Sankar Bharani、L. Raju Chowhan

  DOI：10.1039/d2ob02228a

  日期：——

  Herein, for the first time, we report the asymmetric synthesis of an unexpected stereoisomer of spirohexahydroindole via a trienamine-catalysed remote olefin E/Z isomerisation/[4 + 2]-cycloaddition reaction. The reaction afforded a vast library of aesthetically pleasing spirooxindole hexahydroindole scaffolds with exceptional enantio- and diastereo-selectivities (up to 95% yield, 99% ee and >99 : 1

  在此，我们首次报道了通过三烯胺催化的远程烯烃E / Z不对称合成螺六氢吲哚的意外立体异构体异构化/[4 + 2]-环加成反应。该反应提供了大量美观的螺氧吲哚六氢吲哚支架库，具有出色的对映和非对映选择性（高达 95% 产率、99% ee 和 >99 : 1 dr）。此外，我们展示了对映体纯的螺氧吲哚六氢吲哚的合成转化，分别以优异的收率和选择性合成了具有四个和七个连续立体中心的烷基同系螺氧吲哚六氢吲哚和氟代吡喃八氢吲哚部分。我们还通过 NMR 调查证明了拟议途径的证据。
• Construction of Pyrrolidinyl Spirooxindoles via a 1,3-Dipolar Cycloaddition Reaction of (<i>E</i>)-<i>N</i>-Boc-3-Alkylidene-Indolin-2(3<i>H</i>)ones with Azomethine Ylides
  作者：Zhang-Biao Yu、Xiong-Li Liu、Bo-Wen Pan、Bin Chen、Ying Zhou、Hua-Lin Wang

  DOI：10.1080/00397911.2013.820834

  日期：2014.2.16

  A mild and efficient method for the construction of pyrrolidinyl spirooxindoles via a 1,3-dipolar cycloaddition reaction of (E)-N-Boc-3-alkylidene-indolin-2(3H)ones with azomethine ylides has been established. The presence of an N-Boc group in the indolin-2(3H)ones obviously increased the activity and stereoselectivity of the reaction, affording the desired pyrrolidinyl spirooxindoles 4 with up to 85% yield and up to >99/1 dr value. Furthermore, the antibacterial activity of these compounds against Staphylococcus aureus (ATCC-25825) has been tested at minimum concentration, and some of them exhibit moderate antibacterial activity. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource(s): Full experimental and spectral details.]