3-[(1,1-biphenyl)-4-yl-methylidene]-1,3-dihydro-2H-indol-2-one | 1223026-34-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-[(1,1-biphenyl)-4-yl-methylidene]-1,3-dihydro-2H-indol-2-one
• 英文别名: (E)-3-([1,1'-biphenyl]-4-ylmethylene)indolin-2-one；(3E)-3-(1,1'-biphenyl-4-ylmethylen)-1,3-dihydro-2H-indol-2-one；(3E)-3-[(4-phenylphenyl)methylidene]-1H-indol-2-one
• CAS: 1223026-34-3
• 化学式: C₂₁H₁₅NO
• 分子量: 297.356
• InChiKey: LWZNOKZIYKJXSM-XMHGGMMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-吲哚酮 、 4-氨基乙基联苯 在 氧气 、 iron(II) bromide 作用下， 反应 16.0h， 以91%的产率得到3-[(1,1-biphenyl)-4-yl-methylidene]-1,3-dihydro-2H-indol-2-one
  参考文献：
  名称：

  铁催化氧合吲哚和苄胺的Csp3-H键的有氧氧化缩合反应合成（E）-3-亚烷基亚吲哚啉-2-酮

  摘要：

  描述了铁催化的氧吲哚与苄基胺的氧化缩合直接生成（E）-3-亚烷基亚吲哚啉-2-酮的方法。该程序利用分子氧作为清洁的终端氧化剂。

  DOI：

  10.1002/ejoc.202001300

文献信息

• Oxindole Derivatives: Synthesis and Antiglycation Activity
  作者：Khalid Khan、Momin Khan、Nida Ambreen、Muhammad Taha、Fazal Rahim、Saima Rasheed、Sumayya Saied、Humaira Shafi、Shahnaz Perveen、Muhammad Choudhary

  DOI：10.2174/1573406411309050007

  日期：2013.6.1

  Oxindole derivatives 3-25 have been synthesized from commercially available oxindole by refluxing with different aromatic aldehydes in good yields. Their in vitro antiglycation potential has been evaluated. They showed a varying degree of antiglycation activity with IC50 values ranging between 150.4 - 856.7 µM. 3-[(3-Chlorophenyl)methylidene]- 1,3-dihydro-2H-indol-2-one (IC50 = 150.4 ± 2.5 µM) is the most active compound among the series, better than the standard rutin with an IC50 value 294.5 ± 1.50 µM. The structures of the compounds were elucidated by 1H-NMR and mass spectroscopy and elemental analysis. A limited structure-activity relationship has been developed.

  氧杂吲哚衍生物3-25是通过与不同的芳香醛在回流条件下反应，从市售的氧杂吲哚合成的，产率较高。它们的体外抗糖化潜力已被评估，显示出不同程度的抗糖化活性，其IC50值范围在150.4 - 856.7 µM之间。3-[(3-氯苯基)亚甲基]-1,3-二氢-2H-吲哚-2-酮（IC50 = 150.4 ± 2.5 µM）是该系列中活性最强的化合物，优于标准的芦丁，其IC50值为294.5 ± 1.50 µM。通过1H-NMR、质谱和元素分析对这些化合物的结构进行了阐明，并建立了有限的结构-活性关系。
• Absorption and fluorescence of arylmethylidenoxindoles and isoindigo
  作者：Stanislav Luňák、Petra Horáková、Antonín Lyčka

  DOI：10.1016/j.dyepig.2009.11.001

  日期：2010.5

  spectral features of the parent Z-benzylidenoxindole were compared to those of trans-isoindigo and trans-stilbene. Fluorescence of arylmethylidenoxindoles in solution was not observed, as E–Z isomerization represents a dominant deactivation channel after irradiation; when this geometrical isomerization was sterically hindered at low temperature solvent glass or in solid, fluorescence of planar Z-isomers

  通过酸或碱催化的取代醛与羟吲哚的缩合反应，合成了一系列芳基甲基亚氨基新吲哚。产物形成为Z-和E-异构体的混合物，使用柱色谱分离并通过1 H和13 C NMR鉴定。基于时间相关的密度泛函理论，通过实验和理论研究了取代基对吸收最大值的影响。溶剂玻璃中的低温吸收光谱能够识别0-0振动带的位置。比较了母体Z-苄亚氨基吲哚的光谱特征与tran s-isoindigo和trans的光谱特征-二苯乙烯。溶液中未观察到芳基甲基亚氨基新多酚的荧光，因为E - Z异构化代表辐照后的主要失活通道。当在低温溶剂玻璃或固体中这种几何异构化在空间上受阻时，观察到平面Z-异构体的荧光。
• ANTI-GLYCATION PROPERTIES OF OXINDOLE DERIVATIVES
  申请人：Choudhary Muhammad Iqbal

  公开号：US20150038543A1

  公开（公告）日：2015-02-05

  This invention provides a series of new oxindole derivatives 1-21, evaluated for their antiglycation potential by using in vitro BSA-MG glycation model. These derivatives showed a varying degree of antiglycation activity with IC 50 values ranging between 150-856 μM. Compound 14 (IC 50 =150.4±2.5 μM) was found to be the most potent among all derivatives, even better than the standard inhibitor i.e. rutin (IC 50 =294.5±1.50 followed by compounds 13 and 8 with IC 50 value of 194.40±2.5 and 211.41±4.1 μM, respectively.
• Synthesis of ( <i>E</i> )‐3‐Alkylideneindolin‐2‐ones by an Iron‐Catalyzed Aerobic Oxidative Condensation of Csp ³ –H Bonds of Oxindoles and Benzylamines
  作者：Kovuru Gopalaiah、Ankit Tiwari

  DOI：10.1002/ejoc.202001300

  日期：2020.12.13

  An iron‐catalyzed direct access to (E)‐3‐alkylideneindolin‐2‐ones through oxidative condensation of oxindoles with benzylamines is described. The procedure utilizes molecular oxygen as a clean and terminal oxidant.

  描述了铁催化的氧吲哚与苄基胺的氧化缩合直接生成（E）-3-亚烷基亚吲哚啉-2-酮的方法。该程序利用分子氧作为清洁的终端氧化剂。