ethyl (E)-2-(5-nitro-2-oxoindolin-3-ylidene)acetate | 882040-14-4

• 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: ethyl (E)-2-(5-nitro-2-oxoindolin-3-ylidene)acetate
• 英文别名: (E)-ethyl 2-(5-nitro-2-oxoindolin-3-ylidene)acetate；ethyl (2E)-2-(5-nitro-2-oxo-1H-indol-3-ylidene)acetate
• CAS: 882040-14-4
• 化学式: C₁₂H₁₀N₂O₅
• 分子量: 262.222
• InChiKey: LEEOAXACQAFPHV-RMKNXTFCSA-N

物化性质

• 沸点：
  503.9±50.0 °C(Predicted)
• 密度：
  1.484±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl (E)-2-(5-nitro-2-oxoindolin-3-ylidene)acetate 在 (2S)-2-[二苯基[(三甲基硅酯)氧基]甲基]-吡咯烷 、 4-二甲氨基吡啶 、 邻氟苯甲酸 作用下， 以 氘代氯仿 、 乙腈 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：

  5-硝基靛红 、 乙氧甲酰基亚甲基三苯基膦 以 四氢呋喃 为溶剂， 以80%的产率得到ethyl (E)-2-(5-nitro-2-oxoindolin-3-ylidene)acetate
  参考文献：
  名称：

  吡啶鎓盐的1,3-偶极环加成反应产生的生物碱启发的螺环吲哚†

  摘要：

  据报道，吡啶鎓吡啶化物和3-烯基羟吲哚之间的环加成反应以高收率进行，并且具有非常好的区域和非对映选择性。所得的环加合物具有与生物活性的羟吲哚生物碱（如间苯二酚）相同的立体化学。

  DOI：

  10.1039/c3ob41415a

文献信息

• Alkaloid inspired spirocyclic oxindoles from 1,3-dipolar cycloaddition of pyridinium ylides
  作者：Jonathan Day、Maliha Uroos、Richard A. Castledine、William Lewis、Ben McKeever-Abbas、James Dowden

  DOI：10.1039/c3ob41415a

  日期：——

  Cycloaddition reactions between pyridinium ylides and 3-alkenyl oxindoles that proceed in high yield and with very good regio- and diastereoselectivity are reported. The resulting cycloadducts have the same stereochemistry of biologically active oxindole alkaloids, such as strychnofoline.

  据报道，吡啶鎓吡啶化物和3-烯基羟吲哚之间的环加成反应以高收率进行，并且具有非常好的区域和非对映选择性。所得的环加合物具有与生物活性的羟吲哚生物碱（如间苯二酚）相同的立体化学。
• Stereoselective Synthesis of Tetrahydroindolizines through the Catalytic Formation of Pyridinium Ylides from Diazo Compounds
  作者：Jonathan Day、Ben McKeever-Abbas、James Dowden

  DOI：10.1002/anie.201511047

  日期：2016.5.4

  compounds, pyridines, and electrophilic alkenes to give alkaloid‐inspired tetrahydroindolizidines in high yield with high diastereoselectivity. Hitherto, the catalytic formation of versatile pyridinium ylides from metal carbenes has been poorly developed; the broad utility demonstrated herein sets the stage for the invention of further multicomponent reactions in future.

  市售的铁（III）和铜（I）配合物催化重氮化合物，吡啶和亲电烯烃之间的多组分环加成反应，从而以高收率和高非对映选择性提供了生物碱启发的四氢吲哚并咪唑。迄今为止，由金属卡宾催化形成多用途吡啶鎓叶立德的反应还很不发达。本文证明的广泛用途为将来进一步的多组分反应的发明奠定了基础。
• When Ethyl Isocyanoacetate Meets Isatins: A 1,3-Dipolar/Inverse 1,3-Dipolar/Olefination Reaction for Access to 3-Ylideneoxindoles
  作者：Wen-Kui Yuan、Tao Cui、Wei Liu、Li-Rong Wen、Ming Li

  DOI：10.1021/acs.orglett.8b00217

  日期：2018.3.16

  A new CuI/1,10-phen-catalyzed reaction for the synthesis of 3-ylideneoxindoles from readily available isatins and ethyl isocyanoacetate, in which ethyl isocyanoacetate acts as a latent two-carbon donor like the Wittig reagent, is reported. A tandem procedure including 1,3-dipolar cycloaddition/inverse 1,3-dipolar ring opening/olefination allows the preparation of 3-ylideneoxindoles with broad functional

  据报道，一种新的CuI / 1,10-phen催化的反应可从易得的靛红和异氰基乙酸乙酯合成3-亚苄基吲哚，其中异氰基乙酸乙酯像Wittig试剂一样是潜在的二碳供体。串联程序包括1,3-偶极环加成反应/ 1,3-偶极反环开环反应/烯化反应，可以制备具有宽泛的官能团耐受性的3-亚硝基氧吲哚。
• An efficient one pot regioselective synthesis of a 3,3′-spiro-phosphonylpyrazole-oxindole framework via base mediated [1,3]-dipolar cycloaddition reaction of the Bestmann–Ohira reagent with methyleneindolinones
  作者：Anil M. Shelke、Gurunath Suryavanshi

  DOI：10.1039/c5ob01020a

  日期：——

  regioselective synthesis of racemic 3,3′-spiro-phosphonylpyrazole-oxindole by 1,3-dipolar cycloaddition of an in situ generated anion of dialkyl 1-diazomethylphosphonate from the Bestmann–Ohira reagent (BOR) & methyleneindolinones has been developed. The synthesis affords the highly functionalized pyrazole scaffolds in good yields with excellent regioselectivity under mild reaction conditions within

  通过一锅，从Bestmann-Ohira试剂（BOR）和亚甲基吲哚满酮原位生成的1-重氮甲基膦酸二烷基酯的原位生成的阴离子的1,3-偶极环加成反应，可以高度区域选择性地合成外消旋3,3'-螺代-膦酰基吡唑-恶吲哚发达。在温和的反应条件下，在短的反应时间内，该合成以良好的产率提供了高官能度的吡唑支架，具有出色的区域选择性。
• Steric-Hindrance-Induced Diastereoselective Radical Nitration of 3-Alkylidene-2-oxindoles Followed by Tosylhydrazine-Mediated Sulfonation
  作者：Sayan Pramanik、Pinaki Saha、Prasanta Ghosh、Chhanda Mukhopadhyay

  DOI：10.1021/acs.joc.2c01523

  日期：2023.3.17

  Metal-free radical nitration of the β C–H bond of 3-alkylidene-2-oxindoles with tert-butyl nitrite (TBN) has been explored. Interestingly, (E)-3-(2-(aryl)-2-oxoethylidene)oxindole and (E)-3-ylidene oxindole give different diastereomers on nitration. The mechanistic investigation revealed that the diastereoselectivity was controlled by the size of the functional group. Another transformation of 3-(nitroalkylidene)

  已经探索了 3-alkylidene-2-oxindoles 的 β C-H 键与亚硝酸叔丁酯 (TBN)的金属自由基硝化反应。有趣的是，( E )-3-(2-(aryl)-2-oxoethylidene)oxindole 和 ( E )-3-ylidene oxindole 在硝化时给出不同的非对映异构体。机理研究表明，非对映选择性受官能团大小的控制。通过金属和无氧化剂的甲苯磺酰肼介导的磺化作用，将 3-(硝基亚烷基) 羟吲哚转化为 3-(甲苯磺酰亚烷基) 羟吲哚。这两种方法都具有起始材料容易获得和操作简单的优点。