3-(3-fluorophenylimino)indolin-2-one | 100108-79-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-(3-fluorophenylimino)indolin-2-one
• 英文别名: 3-[(3-fluorophenyl)imino]-1,3-dihydro-2H-indol-2-one；3-(3-fluorophenyl)imino-1H-indol-2-one
• CAS: 100108-79-0
• 化学式: C₁₄H₉FN₂O
• 分子量: 240.237
• InChiKey: GQTOWSLTHYBYJF-UHFFFAOYSA-N

物化性质

• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-羟基-3-丁烯酸 gamma-内酯 、 3-(3-fluorophenylimino)indolin-2-one 在 三乙烯二胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以95%的产率得到3-(3-fluorophenylamino)-3-(5-oxo-2,5-dihydrofuran-2-yl)indolin-2-one
  参考文献：
  名称：

  通过靛红/靛红与呋喃-2(3H)-one 的直接乙烯基羟醛/曼尼希反应简便有效地合成羟吲哚基序

  摘要：

  通过使用 DABCO 作为有机催化剂，在室温下开发了呋喃-2(3H)-one 与靛红或靛红的一种简便有效的直接乙烯基醛醇/曼尼希反应。合成方案是原子经济的，可以轻松获得各种羟吲哚衍生物。这是靛红/靛红与呋喃-2(3H)-one 之间直接进行乙烯基醛醇/曼尼希反应的第一个例子，以提供乙烯基醛醇加合物。简要讨论了该协议的底物范围。

  DOI：

  10.1055/s-0036-1588341
• 作为产物：
  描述：

  苯胺 在 盐酸 、 硫酸 、 盐酸羟胺 、 溶剂黄146 、 sodium sulfate 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 生成 3-(3-fluorophenylimino)indolin-2-one
  参考文献：
  名称：

  Practical Synthesis, Antidepressant, and Anticonvulsant Activity of 3-Phenyliminoindolin-2-one Derivatives

  摘要：

  Herein, a series of 3‐phenyliminoindolin‐2‐one derivatives were designed, synthesized, and screened for their antidepressant and anticonvulsant activities. The IR spectra of the compounds afforded NH stretching (3340–3346 cm−1) bands and C=O stretching (1731–1746 cm−1). In the 1H‐NMR spectra of the compounds, N‐H protons of indoline ring were observed at 10.65–10.89 ppm generally as broad bands, and 13C‐NMR spectra of the compounds C=O were seen at 161.72–169.27 ppm. Interestingly, compounds 3o, 3p and 3r significantly shortened immobility time in the The forced swimming test (FST) and The tail suspension test (TST) at 50 mg/kg dose levels. In addition, compound 3r exhibited higher levels of efficacy than the reference standard fluoxetine but had no effect on locomotor activity in the open‐field test. Compound 3r significantly increased serotonin and norepinephrine and the metabolite 5‐hydroxyindoleacetic acid in mouse brain, suggesting that the effects of compound 3r may be mediated through these neurotransmitters. In the seizure screen, 15 compounds showed some degree against PTZ‐induced seizure at a dose of 100 mg/kg, and the tested compounds did not show any neurotoxicity at a dose of 300 mg/kg in the rotarod test.

  DOI：

  10.1111/cbdd.12668

文献信息

• Synthesis of 1,3-diaryl-spiro[azetidine-2,3′-indoline]-2′,4-diones<i>via</i>the Staudinger reaction:<i>cis</i>- or<i>trans</i>-diastereoselectivity with different addition modes
  作者：Vadim Filatov、Maksim Kukushkin、Juliana Kuznetsova、Dmitry Skvortsov、Viktor Tafeenko、Nikolay Zyk、Alexander Majouga、Elena Beloglazkina

  DOI：10.1039/d0ra02374d

  日期：——

  A new synthetic approach for realizing biologically relevant bis-aryl spiro[azetidine-2,3′-indoline]-2′,4-diones was developed based on Staudinger ketene–imine cycloaddition through the one-pot reaction of substituted acetic acids and Schiff bases in the presence of oxalyl chloride and an organic base. A series of [azetidine-2,3′-indoline]-2′,4-diones were synthesized using this method. For comparison

  基于 Staudinger 烯酮-亚胺环加成反应，通过取代乙酸与 Schiff 的一锅反应，开发了一种实现生物学相关双芳基螺[氮杂环丁烷-2,3'-二氢吲哚]-2',4-二酮的新合成方法碱在草酰氯和有机碱的存在下。使用该方法合成了一系列[氮杂环丁烷-2,3'-二氢吲哚]-2',4-二酮。为了比较，使用已知技术获得相同的化合物，其中乙烯酮是由预合成的酰氯产生的。结果表明，与先前描述的程序不同，在室温下在一锅反应中使用草酰氯生成乙烯酮可以逆转螺内酰胺形成的非对映选择性。
• Pesticidal Mannich Bases Derived from Isatinimines
  作者：Vishnu J. Ram、L. Mishra、H. N. Pandey、A. J. Vlietinck

  DOI：10.1002/jhet.5570230521

  日期：1986.9

  Mannich bases from isatinimines and isatin hydrazones are synthesized for evaluation of their pesticidal activities. Among all the prepared Mannich bases only N-dimethylaminomethyl-3-(p-bromophenyl)iminoindol-2-one exhibited herbicidal activity in pre- and post-emergent tests.

  合成了来自异丁酮和异丁的曼尼希碱，以评估其杀虫活性。在所有制备的曼尼希碱中，只有N-二甲基氨基甲基-3-（对溴苯基）亚氨基吲哚-2-酮在出芽前和出芽后表现出除草活性。
• Indium/Fe(<scp>iii</scp>) – mediated regioselective β-cross-coupling aldol type addition reaction of activated alkenes with isatins/isatinimines in aqueous media
  作者：A. Sanjeeva Kumar、Palakuri Ramesh、G. Santosh Kumar、Jagadeesh Babu Nanubolu、T. Prabhakar Rao、H. M. Meshram

  DOI：10.1039/c5ra07216f

  日期：——

  A highly efficient and regioselective β-cross coupling aldol type addition reaction of activated alkenes with isatin/isatinimine derivatives in the presence of Indium/Fe(iii) in THF/H₂O at room temperature is described.

  描述了在THF/H₂O中，室温下活化烯烃与异喹啉/异喹啉亚胺衍生物在铟/Fe(iii)存在下高效和区域选择性的β-交叉偶联醛缩加反应。
• 10.1021/acs.orglett.4c01395
  作者：Liu, Yijun、Shen, Xiaojiang、Zhu, Pengyan、Hu, Jiang-Miao、Wang, Xuanjun、Ge, Shulin

  DOI：10.1021/acs.orglett.4c01395

  日期：——

  Herein, a gold-catalyzed cascade reaction of yne-enones with iminooxindoles has been developed through a cascade cycloisomerization/(3 + 2) annulation process. This approach provides a straightforward and efficient route for the synthesis of functionalized 3,2′-pyrrolidinyl-spirooxindoles in high reactivity and broad substrate scope with excellent cis-selectivity. Moreover, the subsequent functionalization

  在此，通过级联环异构化/(3 + 2)环化过程开发了金催化的炔烯酮与亚氨基氧吲哚的级联反应。该方法为合成功能化 3,2'-吡咯烷基-螺吲哚提供了一种简单有效的途径，具有高反应活性、广泛的底物范围和优异的顺式选择性。此外，呋喃单元的后续官能化允许螺吲哚衍生物的多样化合成，这些衍生物已表现出良好的抗肿瘤活性。
• Practical Synthesis, Antidepressant, and Anticonvulsant Activity of 3-Phenyliminoindolin-2-one Derivatives
  作者：Jian-Yin Ma、Ying-Chun Quan、Hong-Guo Jin、Xing-Hua Zhen、Xue-Wu Zhang、Li-Ping Guan

  DOI：10.1111/cbdd.12668

  日期：2016.3

  Herein, a series of 3‐phenyliminoindolin‐2‐one derivatives were designed, synthesized, and screened for their antidepressant and anticonvulsant activities. The IR spectra of the compounds afforded NH stretching (3340–3346 cm−1) bands and C=O stretching (1731–1746 cm−1). In the 1H‐NMR spectra of the compounds, N‐H protons of indoline ring were observed at 10.65–10.89 ppm generally as broad bands, and 13C‐NMR spectra of the compounds C=O were seen at 161.72–169.27 ppm. Interestingly, compounds 3o, 3p and 3r significantly shortened immobility time in the The forced swimming test (FST) and The tail suspension test (TST) at 50 mg/kg dose levels. In addition, compound 3r exhibited higher levels of efficacy than the reference standard fluoxetine but had no effect on locomotor activity in the open‐field test. Compound 3r significantly increased serotonin and norepinephrine and the metabolite 5‐hydroxyindoleacetic acid in mouse brain, suggesting that the effects of compound 3r may be mediated through these neurotransmitters. In the seizure screen, 15 compounds showed some degree against PTZ‐induced seizure at a dose of 100 mg/kg, and the tested compounds did not show any neurotoxicity at a dose of 300 mg/kg in the rotarod test.