1-heptylindoline-2,3-dione | 56932-62-8

• 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-heptylindoline-2,3-dione
• 英文别名: 1-Heptylindole-2,3-dione
• CAS: 56932-62-8
• 化学式: C₁₅H₁₉NO₂
• mdl: MFCD00738897
• 分子量: 245.321
• InChiKey: BMZZITFDWPXALB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.466
• 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-heptylindoline-2,3-dione 在 正丁基锂 、 硫酸 作用下， 以 苯 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  The indophenine reaction revisited. Properties of a soluble dialkyl derivative

  摘要：

  The classical indophenine reaction of thiophene with isatin and sulfuric acid has been reinvestigated using N-heptylisatin, which affords soluble reaction products amenable to chromatographic purification. An NMR analysis of the resulting indophenine blue (8) has shown it to be a mixture of all six possible geometric isomers (8a-f) of the previously assumed gross structure. The intermediacy of alcohol 11 in the formation of 8 is strongly supported. In addition, an indophenine analog (9a) derived from only one thiophene unit is reported for the first time.

  DOI：

  10.1021/ja00077a057
• 作为产物：
  描述：

  在 吡啶 、 copper(l) iodide 作用下， 以 二甲基亚砜 为溶剂， 反应 16.0h， 以74%的产率得到1-heptylindoline-2,3-dione
  参考文献：
  名称：

  铜催化的2-氨基苯基乙炔的好氧氧化分子内酰胺化：合成靛红的多米诺骨牌工艺

  摘要：

  已经开发出一种新颖的CuI催化的2-氨基苯基乙炔的氧化酰胺化反应，该反应通过使用露天作为氧气源导致靛红的形成。反应进行得很顺利，并以高收率提供了各种靛红衍生物。这种一锅法反应方案的优点包括使用绿色氧化剂，价格低廉的催化剂和便利的条件，并且易于处理。

  DOI：

  10.1039/c7nj02441j

文献信息

• Rapid umpolung Michael addition of isatin <i>N</i>,<i>N</i>′-cyclic azomethine imine 1,3-dipoles with chalcones
  作者：Guizhou Yue、Dan Jiang、Zhengjie Dou、Sicheng Li、Juhua Feng、Li Zhang、Huabao Chen、Chunping Yang、Zhongqiong Yin、Xu Song、Xiaoxia Liang、Xianxiang Wang、Cuifen Lu

  DOI：10.1039/d1nj00960e

  日期：——

  3,3-Disubstituted oxindoles were prepared rapidly in moderate to excellent yields with promising dr values by the t-BuONa-promoted Michael addition.

  3,3-二取代吲哚通过t-BuONa促进的Michael加成反应迅速制备，产率从中等到优异，具有有希望的dr值。
• Rapid abnormal [3+2]-cycloaddition of isatin <i>N</i>,<i>N</i>′-cyclic azomethine imine 1,3-dipoles with chalcones
  作者：Guizhou Yue、Zhengjie Dou、Zexi Zhou、Li Zhang、Juhua Feng、Huabao Chen、Zhongqiong Yin、Xu Song、Xiaoxia Liang、Xianxiang Wang、Hanbing Rao、Cuifen Lu

  DOI：10.1039/d0nj00887g

  日期：——

  The rapid synthesis of novel dicyclic spiropyrrolidine was reported, using [3+2]-cycloaddition of isatin N,N′-cyclic azomethine imine 1,3-dipoles, generated from the condensation of substituted isatins and pyrazolidones, with chalcones in 2–5 min. The dicyclic spiropyrrolidine oxoindole was smoothly acquired in moderate to excellent yields (35–95%) with high diastereoselectivities (>20 : 1 dr).

  快速报道了新型二环螺吡咯烷的合成，该反应使用取代的靛红和吡唑烷酮与缩醛的缩合反应，在2–5中使用[3 + 2]-靛红N环加成，N'-环偶氮甲亚胺亚胺1,3-偶极。分钟 双环螺吡咯烷氧杂吲哚以中等至优异的收率（35％至95％）平稳地获得，具有非对映选择性高（> 20：1 dr）。
• 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。
• INDOLINONE COMPOUND
  申请人：Kaku Hidetaka

  公开号：US20110009379A1

  公开（公告）日：2011-01-13

  [Problems] A compound, which is useful as an active ingredient for a pharmaceutical composition, for example a pharmaceutical composition for treating constipation-type irritable bowel syndrome, atonic constipation and/or functional gastrointestinal disorder, is provided. [Means for Solution] The present inventors have extensively studied compounds having TRPA1 channel activation activity, and confirmed that an indolinone compound has a TRPA1 channel activation activity, and thus completed the present invention. The indolinone compound of the present invention has a TRPA1 channel activation activity and can be used as an active ingredient of a pharmaceutical composition for preventing and/or treating constipation-type irritable bowel syndrome, atonic constipation and/or functional gastrointestinal disorder or the like.

  [问题] 提供一种化合物，该化合物可用作制药组合物的活性成分，例如用于治疗便秘型肠易激综合征，弛缓性便秘和/或功能性胃肠障碍的制药组合物。 [解决方案] 现有发明人广泛研究了具有TRPA1通道激活活性的化合物，并确认一种吲哚酮化合物具有TRPA1通道激活活性，从而完成了本发明。本发明的吲哚酮化合物具有TRPA1通道激活活性，可用作预防和/或治疗便秘型肠易激综合征，弛缓性便秘和/或功能性胃肠障碍等制药组合物的活性成分。
• 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