1-(3,5-di-tert-butyl-4-hydroxybenzyl)-2,3-dihydro-1H-indole-2,3-dione | 1092474-91-3

• 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-(3,5-di-tert-butyl-4-hydroxybenzyl)-2,3-dihydro-1H-indole-2,3-dione
• 英文别名: 1-(3',5'-di-tert-butyl-4'-hydroxybenzyl)isatin；isatin；1-(3,5-di-tert-butyl-4-hydroxybenzyl)-1H-indole-2,3-dione；N-(3',5'-di-tert-butyl-4'-hydroxybenzyl)isatin；(3,5-Di-t-butyl-4-hydroxyphenyl)methylisatin；1-[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]indole-2,3-dione
• CAS: 1092474-91-3
• 化学式: C₂₃H₂₇NO₃
• 分子量: 365.472
• InChiKey: IQCTUORWXFMIRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(3,5-di-tert-butyl-4-hydroxybenzyl)-2,3-dihydro-1H-indole-2,3-dione 在 六乙基亚磷酸胺 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到1,1'-[3,5-di(tert-butyl)-4-hydroxyphenylmethyl]bis(indolin-3-ylidene)-2,2'-dione
  参考文献：
  名称：

  Isatin derivatives in the reaction with phosphorous hexaethyltriamide. A new approach to the synthesis of isoindigo derivatives

  摘要：

  DOI：

  10.1134/s1070363208100277
• 作为产物：
  描述：

  3,5-二-叔-丁基-4-羟基苄基乙酸酯 、 靛红 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以88.7%的产率得到1-(3,5-di-tert-butyl-4-hydroxybenzyl)-2,3-dihydro-1H-indole-2,3-dione
  参考文献：
  名称：

  具有空间位阻酚片段的靛红酰腙：合成和结构

  摘要：

  获得了具有空间位阻酚片段的靛红酰基腙。它们的结构是使用一维和二维 1H 和 13C NMR 光谱和 X 射线衍射确定的。靛红和 1-(3,5-di-tert-butyl-4-hydroxybenzyl)-l H-indole-2,3-dione 与 3-(3,5-di-tert-butyl- 4-羟基苯基)丙酰肼以C=N键附近的E-和Z-异构体形式存在。E-Z 异构化发生在沸腾的乙醇中。靛红和 3-(3,5-二-叔丁基-4-羟基苯基)丙酰肼的缩合产物的 E-异构体使用 X 射线衍射进行结构表征：该异构体是酰胺基团的顺式构象异构体，并且具有关于 N—N 键的 E 构型。根据 1H NMR 光谱中 NH 质子信号的浓度依赖性数据，

  DOI：

  10.1007/s11172-009-0264-3

文献信息

• 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
• Effect of the Cationic Moiety on the Antimicrobial Activity of Sterically Hindered Isatin 3-Hydrazone Derivatives
  作者：A. V. Bogdanov、M. E. Kadomtseva、S. V. Bukharov、A. D. Voloshina、V. F. Mironov

  DOI：10.1134/s107042802003032x

  日期：2020.3

  AbstractWater-soluble 1-(3,5-di-tert-butyl-4-hydroxybenzyl)isatin 3-acylhydrazones containing an acyclic, bicyclic, or pyridinium quaternary ammonium center in the acyl moiety showed antibacterial activity against some gram-positive bacteria. Derivatives with a 2,3-dimethylpyridine or diazabicyclooctane fragment exhibited the highest activity against S. aureus and B. cereus as expressed by the minimum

  摘要在酰基部分中含有无环，双环或吡啶鎓季铵中心的水溶性1-（3,5-二叔丁基-4-羟基苄基）异丁香3-酰基hydr显示对某些革兰氏阳性细菌具有抗菌活性。具有2,3-二甲基吡啶或二氮杂双环辛烷片段的衍生物表现出对金黄色葡萄球菌和蜡状芽孢杆菌的最高活性，这是由最低杀菌浓度表示的，并且其活性是氯霉素的4倍。
• Synthesis and Structure of Hybrid Compounds Based on Phosphoryl Acetic Acid Hydrazide, Isatin, and Sterically Hindered Phenols
  作者：I. A. Litvinov、S. V. Bukharov、F. A. Karamov、R. A. Khabibullina、N. I. Akylbekov、A. R. Burilov、R. G. Tagasheva、E. L. Gavrilova

  DOI：10.1134/s0022476619110143

  日期：2019.11

  In order to obtain novel biologically active substances with various types of activity, hybrid compounds based on 2-(diphenylphosphoryl)acetohydrazide, isatin, and sterically hindered phenols are synthesized. Their molecular and crystal structures are determined by X-ray crystallography.

  为了获得具有各种活性的新型生物活性物质，合成了基于 2-（二苯基磷酰基）乙酰肼、靛红和位阻酚的杂化化合物。它们的分子和晶体结构由 X 射线晶体学确定。
• Isatin Derivatives Containing Sterically Hindered Phenolic Fragment and Water-Soluble Acyl Hydrazones on Their Basis: Synthesis and Antimicrobial Activity
  作者：A. V. Bogdanov、I. F. Zaripova、A. D. Voloshina、A. S. Strobykina、N. V. Kulik、S. V. Bukharov、V. F. Mironov

  DOI：10.1134/s1070363218010097

  日期：2018.1

  acetate and the Girard’s reagent T has afforded a series of novel water-soluble isatin-3-acyl hydrazones containing a sterically hindered phenolic fragment in position 1 of the heterocycle; antimicrobial activity of the products has been estimated. It has been shown that the isatin derivatives with bromine or methoxy substituent in the benzo fragment as well as the acyl hydrazones containing 5-methyl or

  靛红衍生物与3,5-二（叔丁基）-4-羟基苄基乙酸酯和吉拉德试剂T的缩合反应提供了一系列新型的水溶性Isatin-3-酰基，在位置1上含有空间受阻酚片段杂环的; 已经估计了产品的抗菌活性。已经表明，在苯并片段中具有溴或甲氧基取代基的靛红衍生物以及含有5-甲基或5-乙基的酰基对金黄色葡萄球菌和蜡状芽孢杆菌最活跃。
• Synthesis and Antibacterial Activity of Sulfanilamides Containing Sterically Hindered Phenol Fragments
  作者：S. V. Bukharov、A. R. Burilov、R. G. Tagasheva、G. N. Nugumanova、E. V. Nikitina、N. A. Mukmeneva

  DOI：10.1134/s1070428021100080

  日期：2021.10

  Abstract New sulfanilamide derivatives containing sterically hindered phenol fragments have been synthesized via modification of the amino group by reaction with 3,5-di-tert-butyl-4-hydroxybenzyl acetate and diazotization followed by diazo coupling with 2,4-di-tert-butylphenol. 4-Aminobenzenesulfonamide derivatives at the sulfonamide group have been obtained by converting acetyl-protected 4-aminobenzenesulfonyl

  摘要 通过与 3,5-二叔丁基-4-羟基苄基乙酸酯反应和重氮化，然后与 2,4-二叔丁基苯酚重氮偶联来修饰氨基，合成了含有空间位阻酚片段的新型磺胺衍生物. 通过将乙酰基保护的 4-氨基苯磺酰氯转化为相应的磺酰肼，并将后者与 3,5-二叔丁基-4-羟基苄基乙酸酯、位阻羟基苯甲醛和N -(3,5-二叔-丁基-4-羟基苄基）靛红。用位阻酚片段修饰磺胺显着提高了抗菌活性。