1-nonylindoline-2,3-dione | 79183-25-8

• 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: 1-nonylindoline-2,3-dione
• 英文别名: BChE-IN-25；1-nonylindole-2,3-dione
• CAS: 79183-25-8
• 化学式: C₁₇H₂₃NO₂
• 分子量: 273.375
• InChiKey: HIXIRXUJJGRZFW-UHFFFAOYSA-N

物化性质

• 沸点：
  400.8±28.0 °C(predicted)
• 密度：
  1.069±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-nonylindoline-2,3-dione 在 六乙基亚磷酸胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成 C₃₄H₄₆N₂O₂
  参考文献：
  名称：

  Novel isoindigo derivatives bearing long-chain N-alkyl substituents: Synthesis and self-assemble behavior

  摘要：

  A mild, catalyst-free and simple synthesis of 1,1'-di(n-alkyl)-isoindigo via the reaction of substituted isatins with tris(diethylamino) phosphine is reported. Their self-assembly in water-DMF (50% v/v) solution was investigated. Unexpectedly, no surface activity was observed for compound 2h. Spectrophotometry and fluorimetry allowed determining critical micelle concentration (0.1 mM and 0.8 mM respectively). Aggregation numbers of 8 and sizes of aggregates were determined. (C) 2014 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.cplett.2014.01.026
• 作为产物：
  描述：

  1-溴壬烷 、 isatin sodium salt 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 1-nonylindoline-2,3-dione
  参考文献：
  名称：

  Novel indolin-2-one-substituted methanofullerenes bearing long n-alkyl chains: synthesis and application in bulk-heterojunction solar cells

  摘要：

  一种简单、高产率且原子经济的方法是利用富勒烯C60与N-烷基异吲哚酮在三(二乙基氨基)膦存在下反应，形成新型长链烷基吲哚酮取代的甲基富勒烯（AIMs）的改性。研究了AIMs的光吸收、电化学性质和溶解性。制备了聚（3-己基噻吩-2,5-二基）（P3HT）/AIMs太阳能电池，并研究了AIM烷基链长度和P3HT:AIM比例对太阳能电池性能的影响。在P3HT/AIM器件中，当P3HT:AIM重量比为1:0.4时，具有十六烷基和十二烷基取代基的AIMs的功率转换效率约为2％。根据光学和原子力显微镜数据，我们建议AIMs与[6,6]-苯基-C61-丁酸甲酯（PCBM）不同，不会干扰P3HT的结晶领域。此外，更溶解的AIMs与P3HT结晶相的混溶性并不更好。

  DOI：

  10.3762/bjoc.10.111

文献信息

• Design, synthesis and <i>in vitro</i> evaluation of the hybrids of oxindolylidene and imidazothiazolotriazine as efficient antiproliferative agents
  作者：Alexei N. Izmest’ev、Lada V. Anikina、Igor E. Zanin、Natalya G. Kolotyrkina、Ekaterina S. Izmalkova、Angelina N. Kravchenko、Galina A. Gazieva

  DOI：10.1039/d2nj01454h

  日期：——

  as a lead compound in an effort to discover antiproliferative agents based on oxindolylidene derivatives of imidazothiazolotriazine. A broadened structural optimization using an earlier developed efficient synthetic route provided 17 new oxindolylidene imidazothiazolotriazines which displayed evident antiproliferative activity in cellular assays (GI50 0.60–8.37 μM). The most potent compounds 5d–s (GI50

  1,3-Diethyl-6-oxindolylidenetetrahydroimidazo[4,5- e ]thiazolo[3,2 - b ]-1,2,4-triazine-2,7-dione 在氮原子上具有 2-丙基取代基oxindole 片段 ( 1d ) 之前被确定为先导化合物，以努力发现基于咪唑噻唑并三嗪的 oxindolylidene 衍生物的抗增殖剂。使用较早开发的有效合成路线进行了扩大的结构优化，提供了 17 种新的 oxindolylidene 咪唑噻唑并三嗪，它们在细胞测定中显示出明显的抗增殖活性 (GI 50 0.60–8.37 μM)。最有效的化合物5d–s (GI 50 < 4.5 μM) 含有 1,3-二乙基四氢咪唑[4,5- e]噻唑并[2,3 - c ]-1,2,4-三嗪核心和羟吲哚片段氮原子上的烷基取代基。在羟吲哚片段的氮原子上具有戊基取代基的化合物5m具
• Synthesis and structure of new oxoindoles
  作者：F. Z. Macaev、O. M. Radul、I. N. Shterbet、S. I. Pogrebnoi、N. S. Sucman、S. T. Malinovskii、A. N. Barba、M. Gdaniec

  DOI：10.1007/s10593-007-0045-6

  日期：2007.3
• 10.1134/s1070363224030071
  作者：Bogdanov、Samorodov、Valiullina、Akylbekov、Voloshina、Lyubina、Amerkhanova、Saitova、Pashirova、Tsivileva、Mironov

  DOI：10.1134/s1070363224030071

  日期：——
• Novel isoindigo derivatives bearing long-chain N-alkyl substituents: Synthesis and self-assemble behavior
  作者：Andrei V. Bogdanov、Tatiana N. Pashirova、Lenar I. Musin、Dmitry B. Krivolapov、Lucia Ya. Zakharova、Vladimir F. Mironov、Alexander I. Konovalov

  DOI：10.1016/j.cplett.2014.01.026

  日期：2014.2

  A mild, catalyst-free and simple synthesis of 1,1'-di(n-alkyl)-isoindigo via the reaction of substituted isatins with tris(diethylamino) phosphine is reported. Their self-assembly in water-DMF (50% v/v) solution was investigated. Unexpectedly, no surface activity was observed for compound 2h. Spectrophotometry and fluorimetry allowed determining critical micelle concentration (0.1 mM and 0.8 mM respectively). Aggregation numbers of 8 and sizes of aggregates were determined. (C) 2014 Elsevier B. V. All rights reserved.
• Novel indolin-2-one-substituted methanofullerenes bearing long <i>n</i>-alkyl chains: synthesis and application in bulk-heterojunction solar cells
  作者：Irina P Romanova、Andrei V Bogdanov、Inessa A Izdelieva、Vasily A Trukhanov、Gulnara R Shaikhutdinova、Dmitry G Yakhvarov、Shamil K Latypov、Vladimir F Mironov、Vladimir A Dyakov、Ilya V Golovnin、Dmitry Yu Paraschuk、Oleg G Sinyashin

  DOI：10.3762/bjoc.10.111

  日期：——

  An easy, high-yield and atom-economic procedure of a C₆₀ fullerene modification using a reaction of fullerene C₆₀ with N-alkylisatins in the presence of tris(diethylamino)phosphine to form novel long-chain alkylindolinone-substituted methanofullerenes (AIMs) is described. Optical absorption, electrochemical properties and solubility of AIMs were studied. Poly(3-hexylthiophene-2,5-diyl) (P3HT)/AIMs solar cells were fabricated and the effect of the AIM alkyl chain length and the P3HT:AIM ratio on the solar cell performance was studied. The power conversion efficiencies of about 2% were measured in the P3HT/AIM devices with 1:0.4 P3HT:AIM weight ratio for the AIMs with hexadecyl and dodecyl substituents. From the optical and AFM data, we suggested that the AIMs, in contrast to [6,6]-phenyl-C₆₁-butyric acid methyl ester (PCBM), do not disturb the P3HT crystalline domains. Moreover, the more soluble AIMs do not show a better miscibility with the P3HT crystalline phase.

  一种简单、高产率且原子经济的方法是利用富勒烯C60与N-烷基异吲哚酮在三(二乙基氨基)膦存在下反应，形成新型长链烷基吲哚酮取代的甲基富勒烯（AIMs）的改性。研究了AIMs的光吸收、电化学性质和溶解性。制备了聚（3-己基噻吩-2,5-二基）（P3HT）/AIMs太阳能电池，并研究了AIM烷基链长度和P3HT:AIM比例对太阳能电池性能的影响。在P3HT/AIM器件中，当P3HT:AIM重量比为1:0.4时，具有十六烷基和十二烷基取代基的AIMs的功率转换效率约为2％。根据光学和原子力显微镜数据，我们建议AIMs与[6,6]-苯基-C61-丁酸甲酯（PCBM）不同，不会干扰P3HT的结晶领域。此外，更溶解的AIMs与P3HT结晶相的混溶性并不更好。