1-Hexadecyl-1H-indole-2,3-dione | 28035-35-0

• 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-Hexadecyl-1H-indole-2,3-dione
• 英文别名: 1-hexadecylindole-2,3-dione
• CAS: 28035-35-0
• 化学式: C₂₄H₃₇NO₂
• 分子量: 371.563
• InChiKey: JLUGWHXZCKLPBY-UHFFFAOYSA-N

物化性质

• 沸点：
  490.8±28.0 °C(Predicted)
• 密度：
  1.000±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  27
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 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-Hexadecyl-1H-indole-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 1,1'-dihexadecyl-[3,3'-biindolinylidene]-2,2'-dione
  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：

  苯胺 在 盐酸羟胺 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 6.5h， 生成 1-Hexadecyl-1H-indole-2,3-dione
  参考文献：
  名称：

  基于 1-十六烷基靛红衍生物的光引发系统

  摘要：

  合成了六种新的靛红1-十六烷基衍生物，其5位上具有不同的取代基。测定了它们的光谱和电化学特性。所有获得的靛红都可以在溶液中、在叔胺存在下、在可见光照射下发生光还原。该过程的有效速率常数随着胺氧化电势的降低、靛红还原电势的增加而增加，并且在溴代衍生物的情况下达到最大值。在三乙胺存在下，所得1-十六烷基靛红在蓝色光谱区的近紫外光和可见光作用下引发二甲基丙烯酸酯OCM-2的光聚合。从一种靛红转变为另一种靛红期间，光还原和光聚合的速率常数平行变化。

  DOI：

  10.1007/s11172-023-3955-2

文献信息

• Design and synthesis of N-alkyl oxindolylidene acetic acids as a new class of potent Cdc25A inhibitors
  作者：Rumiko Shimazawa、Masami Kuriyama、Ryuichi Shirai

  DOI：10.1016/j.bmcl.2008.04.027

  日期：2008.6

  The oxindolylidene acetic acids having long N-alkyl chains exhibited strong inhibitory activity toward dual specificity phosphatase Cdc25A.

  具有长N-烷基链的二氧杂环丁烯乙酸对双特异性磷酸酶Cdc25A表现出强抑制活性。
• Synthesis and antimicrobial activity evaluation of some novel water-soluble isatin-3-acylhydrazones
  作者：Andrei V. Bogdanov、Ilyuza F. Zaripova、Alexandra D. Voloshina、Anastasia S. Strobykina、Natalia V. Kulik、Sergey V. Bukharov、Julia K. Voronina、Ayrat R. Khamatgalimov、Vladimir F. Mironov

  DOI：10.1007/s00706-017-2049-y

  日期：2018.1

  AbstractBy acid-catalyzed reaction of substituted isatins with Girard’s reagent T, new water-soluble isatin-3-acylhydrazones were obtained with high yields. Their antimicrobial activity was evaluated. Selective activity against Gram-positive bacteria (S. aureus 209p and B. cereus 8035) and yeast-like fungus Candida albicans 855–653 along with low hematoxicity was established. Graphical abstract

  摘要通过取代的靛红与吉拉德试剂T的酸​​催化反应，可以高收率获得新型的水溶性靛红3-酰基azo。评价了它们的抗菌活性。建立了针对革兰氏阳性细菌（金黄色葡萄球菌209p和蜡状芽孢杆菌8035）和酵母样真菌白色念珠菌855 – 653的选择性活性，同时具有较低的血液毒性。 图形概要
• Synthesis of novel spiro[pyrazolo[4,3- d ]pyrimidinones and spiro[benzo[4,5]thieno[2,3- d ]pyrimidine-2,3′-indoline]-2′,4(3H)-diones and their evaluation for anticancer activity
  作者：Ismail、Bhaskar Kuthati、Gangadhar Thalari、Venkatesham Bommarapu、Chaitanya Mulakayala、Suresh Kumar Chitta、Naveen Mulakayala

  DOI：10.1016/j.bmcl.2017.01.088

  日期：2017.3

  efficient and novel method for the preparation of spiro[pyrazolo[4,3-d]pyrimidin]-7'(1'H)-ones by the condensation of 4-amino-1-methyl-3-propylpyrazole-5-carboxamide with ketones under mild conditions using catalytic InCl3 was reported. This method has been extended for the synthesis of novel spiro[benzo[4,5]thieno[2,3-d]pyrimidine-2,3'-indoline]-2',4(3H)-dione which are having potential applications in medicinal

  通过4-氨基-1-甲基-3-丙基吡唑-5-羧酰胺缩合制备螺并[吡唑并[4,3-d]嘧啶] -7'（1'H）-的高效新颖方法报道了在温和条件下使用催化型InCl3与酮的反应。该方法已扩展到具有潜在应用的新型螺[苯并[苯并[4,5]噻吩并[2,3-d]嘧啶-2,3'-二氢吲哚] -2'，4（3H）-二酮的合成在药物化学中。评价所有合成的化合物在体外对癌细胞系的抗增殖特性，发现几种化合物具有活性。进一步的体外研究表明，抑制沉默调节蛋白可能是这些分子起作用的可能机制。
• 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。
• Tunable amphiphilic π-systems based on isatin derivatives containing a quaternary ammonium moiety: The role of alkyl chain length in biological activity
  作者：T.N. Pashirova、A.V. Bogdanov、I.F. Zaripova、E.A. Burilova、A.E. Vandyukov、A.S. Sapunova、I.I. Vandyukova、A.D. Voloshina、V.F. Mironov、L.Ya. Zakharova

  DOI：10.1016/j.molliq.2019.111220

  日期：2019.9

  This work deals with polyfunctional biocompatible amphiphilic isatin derivatives. Isatin-3-acylhydrazones containing a quaternary ammonium moiety (Is-Q-n) with varying hydrophobicity (R = CnH2n+1, where n = 10, 12, 14, 16, 18, 20) were synthesized. Tunable self-assembly behavior, morphology of nanostructures, and their biological activity were modulated by hydrophilic-lipophilic balance of π-amphiphiles

  这项工作涉及多功能生物相容性两亲性伊斯廷衍生物。合成包含具有变化的疏水性（R = C n H 2n + 1，其中n  = 10、12、14、16、16、18、20）的季铵部分（Is-Qn）的Isatin-3-酰基hydr 。可调节的自组装行为，纳米结构的形态及其生物学活性受到π-两亲物的亲水亲脂平衡和溶剂极性的调节。 通过张力测定，电导测定，IR和UV-Vis光谱，荧光测定和动态光散射研究了Is-Qn的自组装。 已经解释了在长烷基链长度上的物理化学参数的出乎意料的值。Is-Q-16的CAC低于经典表面活性剂CTAB的CMC。观察到溶剂诱导的Is-Q-16自组装。疏水染料Orange OT在Is-Q-10溶液中的溶解度是在CTAB溶液中的两倍。发现了尺寸为50 nm和100 nm的Is-Qn自组装结构，其浓度范围为0.01 mM（低于CAC）至10 mM。Is-Q-10形成大小为3 nm的小