5-nitro-indole-2,3-dione 3-phenylhydrazone

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 5-nitro-indole-2,3-dione 3-phenylhydrazone
• 英文别名: 3-(2-phenylhydrazono)-5-nitroindolin-2-one；5-nitro-3-(2-phenylhydrazineylidene)indolin-2-one
• 化学式: C₁₄H₁₀N₄O₃
• 分子量: 282.258
• InChiKey: FLCCIMVPZLAFPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.36
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  96.63
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  2-(5-nitro-2-oxoindolin-3-ylidene)malononitrile 、 苯肼 以 乙醇 为溶剂， 反应 10.0h， 以81%的产率得到5-nitro-indole-2,3-dione 3-phenylhydrazone
  参考文献：
  名称：

  Investigation of Reactions Between Binucleophilic Reagents with 2-(2-Oxindolin-3-ylidene)malononitrile Derivatives

  摘要：

  将肼和硫代半缩氨基脲对2-(2-氧代吲哚啉-3-亚基)丙二腈衍生物1进行亲核加成后，脱除丙二腈，分别得到3-(2-芳基亚肼基)吲哚啉-2-酮和1-(2-氧代吲哚啉-3-亚基)硫代半缩氨基脲。同样地，化合物1与4-取代的硫代半缩氨基脲反应后，经过消除和环化，生成螺(吲哚酮-3,2'-[1,3,4]噻二唑)-2-酮。综上所述，这些对靛红和取代靛红的亲核反应都得到了相同的产物。

  DOI：

  10.2174/1570178611310070004

文献信息

• Simple and efficient approach for synthesis of hydrazones from carbonyl compounds and hydrazides catalyzed by meglumine
  作者：Mo Zhang、Ze-Ren Shang、Xiao-Tang Li、Jia-Nan Zhang、Yong Wang、Kang Li、Yang-Yang Li、Zhan-Hui Zhang

  DOI：10.1080/00397911.2016.1258476

  日期：2017.1.17

  ABSTRACT A simple, environmentally benign protocol for synthesis of hydrazones from carbonyl compounds and hydrazides has been developed in the presence of meglumine in aqueous-ethanol media at room temperature. The salient features of the present protocol are mild reaction conditions, short reaction time, high yields, operational simplicity, metal-free, applicability toward large-scale synthesis, and biodegradable

  摘要 在葡甲胺存在的情况下，在室温下，在乙醇水溶液中，已经开发出一种简单、环境友好的方案，用于从羰基化合物和酰肼合成腙。本协议的显着特点是反应条件温和、反应时间短、产量高、操作简单、不含金属、适用于大规模合成以及可生物降解且价格低廉的催化剂。图形概要
• Indium(<scp>iii</scp>)-catalyzed efficient synthesis of 3-arylhydrazonoindolin-2-ones and their fluorescent metal sensing studies
  作者：Shreedhar Devkota、Sonaimuthu Mohandoss、Yong Rok Lee

  DOI：10.1039/d1nj05715d

  日期：——

  In(iii)-catalyzed strategy for the preparation of 3-arylhydrazonoindolin-2-ones from 3-diazoindoles is developed and used for Fe³⁺ and Hg²⁺ ion sensing.

  研发了一种以In(iii)为催化剂的策略，用于从3-重氮吲哚制备3-芳基肼基吲哚啉-2-酮，并用于Fe3+和Hg2+离子传感。
• Visible-light-absorbing C–N cross-coupling for the synthesis of hydrazones involving C(sp²)–H/C(sp³)–H functionalization
  作者：Ambuj Kumar Kushwaha、Suresh Kumar Maury、Arsala Kamal、Himanshu Kumar Singh、Shikha Pandey、Sundaram Singh

  DOI：10.1039/d2cc07001d

  日期：——

  An efficient C–N cross-coupling approach for the synthesis of hydrazones was developed through C(sp2)–H and C(sp3)–H functionalization of indole and methylarene under visible light irradiation using photocatalyst eosin Y, ethanol:water as a green solvent and atmospheric air as an oxidant. With the aid of eosin Y, the C–H bonds of indole and methylarenes were activated followed by coupling with arylhydrazines

  通过 C(sp 2 )–H 和 C(sp 3)–H 功能化吲哚和甲基芳烃在可见光照射下使用光催化剂曙红 Y，乙醇：水作为绿色溶剂和大气空气作为氧化剂。在曙红 Y 的帮助下，吲哚和甲基芳烃的 C-H 键被激活，然后与芳基肼偶联。该程序适用于具有良好官能团相容性的各种底物，提供了一种创造性的方法，可以用廉价且易于获得的原材料制造腙。没有金属、低成本、环境友好、绿色溶剂、无毒、易于处理以及利用可见光等可再生能源是该方法的一些主要优势。
• Hydrazone derivatives, their preparation and use
  申请人：NEUROSEARCH A/S

  公开号：EP0503349A1

  公开（公告）日：1992-09-16

  A method of treatment with compounds having the formula wherein n is 0 or 1; R¹ is hydrogen, C₁₋₆-alkyl which may be branched, C₃₋₇-cycloalkyl, benzyl, phenyl which may be substituted, acyl, hydroxy, C₁₋₆-alkoxy, CH₂CO₂R' wherein R' is hydrogen or C₁₋₆-alkyl which may be branched, CH₂CN, CH₂CONRIVRV wherein RIV and RV independently are hydrogen or C₁₋₆-alkyl, or CH₂C(=NOH)NH₂; R² is pyridyl or phenyl, both of which may be substituted one or more times preferably in the ortho and para positions with halogen, CF₃, NO₂, CN, phenyl, SO₂NR''R''' wherein R'' and R''' independently are hydrogen, benzyl, or C₁₋₆-alkyl; R⁴, R⁵, R⁶, R⁷ independently are hydrogen, C₁₋₆-alkyl which may be branched, phenyl, halogen, C₁₋₆-alkoxy, NO₂, CN, CF₃, or SO₂NR¹¹R¹² wherein R¹¹ and R¹² independently are hydrogen, benzyl, or C₁₋₆-alkyl; or R⁶ and R⁷ together form an additional 4 to 8 membered carbocyclic ring which may be aromatic or partial saturated and which may be substituted with halogen, NO₂, CF₃, CN, SO₂NR¹³R¹⁴ wherein R¹³ and R¹⁴ independently are hydrogen, benzyl, or C₁₋₆-alkyl, and R⁴ and R⁵ have the meanings set forth above; or R⁴ and R⁵ together form an additional 4 to 8 membered carbocyclic ring which may be aromatic or partial saturated and which may be substituted with halogen, NO₂, CF₃, CN, SO₂NR¹³R¹⁴ wherein R¹³ and R¹⁴ independently are hydrogen, benzyl, or C₁₋₆-alkyl, and R⁶ and R⁷ have the meanings set forth above. Certain of the compounds are novel. The compounds and pharmaceutical compositions containing the compounds are useful in the treatment of central nervous system disorders and especially conditions sensitive to excitatory amino acids.

  一种用具有以下式子的化合物进行处理的方法 其中 n 是 0 或 1； R¹ 是氢、C₁₋₆-烷基（可为支链）、C₃₋₇-环烷基、苄基、苯基（可被取代）、 酰基、羟基、C₁₋₆-烷氧基、CH₂CO₂R'（其中 R'为氢或 C₁₋₆- 烷基，可为支链）、CH₂CN、CH₂CONRIVRV（其中 RIV 和 RV 独立地为氢或 C₁₋₆-烷基）或 CH₂C(=NOH)NH₂； R² 是吡啶基或苯基，二者最好在正位和对位被卤素、CF₃、NO₂、CN、苯基、SO₂NR''R'''取代一次或多次，其中 R'' 和 R'''' 独立地为氢、苄基或 C₁₋₆-烷基； R⁴、R⁵、R⁶、R⁷ 各自为氢、C₁₋₆-烷基（可为支链）、苯基、卤素、C₁₋₆-烷氧基、NO₂、CN、CF₃或 SO₂NR¹R¹²，其中 R¹ 和 R¹² 独立地是氢、苄基或 C₁₋₆-烷基；或 R⁶ 和 R⁷ 共同形成另外一个 4 至 8 个成员的碳环，该碳环可为芳香族或部分饱和环，可被卤素、NO₂、CF₃、CN、SO₂NR¹³R¹⁴，其中 R¹³ 和 R¹⁴ 独立为氢、苄基或 C₁₋₆ 烷基，且 R⁴ 和 R⁵ 具有上述含义； 或 R⁴ 和 R⁵ 共同形成一个额外的 4 至 8 位碳环，该碳环可为芳香族或部分饱和环，可被卤素、NO₂、CF₃、CN、SO₂NR¹³R¹⁴，其中 R¹³ 和 R¹⁴ 独立地为氢、苄基或 C₁₋₆ 烷基，且 R⁶ 和 R⁷ 具有上述含义。 某些化合物具有新颖性。 这些化合物和含有这些化合物的药物组合物可用于治疗中枢神经系统疾病，特别是对兴奋性氨基酸敏感的疾病。
• Synthesis and antibacterial screening of hydrazones, Schiff and Mannich bases of isatin derivatives
  作者：Seshaiah Krishnan Sridhar、Muniyandy Saravanan、Atmakuru Ramesh

  DOI：10.1016/s0223-5234(01)01255-7

  日期：2001.8

  Schiff bases and hydrazones of substituted isatins (1-28), were prepared by reacting isatin and aromatic primary amines/hydrazines. A new series of the corresponding N-Mannich base (29-35) was synthesised by reacting them with formaldehyde and diphenyl amine. The chemical structures were confirmed by means of H-1-NMR, IR spectral data and elemental analysis. The compounds were screened for antibacterial activity against seven Gram (+) and seven Gram (-) standard and pathological bacterial strains by the paper disc diffusion technique. The minimum inhibitory concentrations of the active compounds were determined. 1-Diphenyl amino-methyl-3-(4-bromo phenylimino)-1,3-dihydro-indol-3-one (30) and 3-(4-bromo phenylimino)-5-nitro-1,3-dihydroindol-3-one (13) were found to be the most actives compounds of the series. Mannich bases exhibited higher activity than the corresponding Schiff bases. (C) 2001 Editions scientifiques et medicales Elsevier SAS.