2-丁基-4-硝基异吲哚-1,3-二酮 | 54395-36-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 中文名称: 2-丁基-4-硝基异吲哚-1,3-二酮
• 英文名称: 2-butyl-4-nitroisoindoline-1,3-dione
• 英文别名: N-butyl-3-nitrophthalimide；2-butyl-4-nitro-isoindoline-1,3-dione；2-Butyl-4-nitro-isoindolin-1,3-dion；3-nitro-N-butylphthalimide；1H-Isoindole-1,3(2H)-dione, 2-butyl-4-nitro-；2-butyl-4-nitroisoindole-1,3-dione
• CAS: 54395-36-7
• 化学式: C₁₂H₁₂N₂O₄
• 分子量: 248.238
• InChiKey: OLOUZLFUNQCQEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  83.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-丁基-4-硝基异吲哚-1,3-二酮 在 硫酸 、 palladium 10% on activated carbon 、 氢气 、 sodium nitrite 作用下， 以 甲醇 、 水 为溶剂， 反应 13.5h， 生成 N-butyl-3-hydroxyphthalimide
  参考文献：
  名称：

  A phthalimide-based fluorescent probe for thiophenol detection in water samples and living cells with a large Stokes shift

  摘要：

  A phthalimide-based fluorescent probe for the detection of thiophenol was developed based on the combination of photo-induced electron transfer (PET) and excited-state intramolecular proton transfer (ESIPT) mechanisms. This probe displays high sensitivity and good selectivity toward thiophenol with a large Stokes shift (161 nm) and a low detection limit (3.5 nM, based on S/N=3). Furthermore, the applications of this probe for quantitative detection of thiophenol in real water samples and imaging intracellular thiophenol in living cells were successfully demonstrated. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.08.074
• 作为产物：
  描述：

  3-硝基邻苯二甲酸酐 以 正己烷 、 二氯甲烷 为溶剂， 反应 0.66h， 生成 2-丁基-4-硝基异吲哚-1,3-二酮
  参考文献：
  名称：

  Chemical Derivatization for Electrospray Ionization Mass Spectrometry. 1. Alkyl Halides, Alcohols, Phenols, Thiols, and Amines

  摘要：

  Derivatization strategies and specific derivatization reactions for conversion of simple alkyl halides, alcohols, phenols, thiols, and amines to ionic or solution-ionizable derivatives, that is ''electrospray active'' (ES-active) forms of the analyte, are presented. Use of these reactions allows detection of analytes among those listed that are not normally amenable to analysis by electrospray ionization mass spectrometry (ES-MS). In addition, these reactions provide for analysis specificity and flexibility through functional group specific derivatization and through the formation of derivatives that can be detected in positive ion or in negative ion mode. For a few of the functional groups, amphoteric derivatives are formed that can be analyzed in either positive or negative ion modes. General synthetic strategies for transformation of members of these five compound classes to ES-active species are presented along with illustrative examples of suitable derivatives. Selected derivatives were prepared using model compounds and the ES mass spectra obtained for these derivatives are discussed. The analytical utility of derivatization for ES-MS analysis is illustrated in three experiments: (1) specific detection of the major secondary alcohol in oil of peppermint, (2) selective detection of phenols within a synthetic mixture of phenols, and (3) identification of the medicinal amines within a commercially available cold medication as primary, secondary or tertiary.

  DOI：

  10.1021/ac00080a016

文献信息

• Metal-Free, Rapid, and Highly Chemoselective Reduction of Aromatic Nitro Compounds at Room Temperature
  作者：Mingyeong Jang、Taeho Lim、Byoung Yong Park、Min Su Han

  DOI：10.1021/acs.joc.1c01431

  日期：2022.1.21

  this study, we developed a metal-free and highly chemoselective method for the reduction of aromatic nitro compounds. This reduction was performed using tetrahydroxydiboron [B2(OH)4] as the reductant and 4,4′-bipyridine as the organocatalyst and could be completed within 5 min at room temperature. Under optimal conditions, nitroarenes with sensitive functional groups, such as vinyl, ethynyl, carbonyl

  在这项研究中，我们开发了一种无金属且高度化学选择性的芳族硝基化合物还原方法。这种还原是使用四羟基二硼[B 2 (OH) 4 ] 作为还原剂和4,4'-联吡啶作为有机催化剂进行的，并且可以在室温下在5分钟内完成。在最佳条件下，具有敏感官能团（如乙烯基、乙炔基、羰基和卤素）的硝基芳烃以优异的选择性转化为相应的苯胺，同时避免了敏感官能团的不良还原。
• A selective and sensitive phthalimide-based fluorescent probe for hydrogen sulfide with a large Stokes shift
  作者：Liu Yang、Xingjiang Liu、Li Gao、Fengpei Qi、Huihui Tian、Xiangzhi Song

  DOI：10.1039/c5ra19081a

  日期：——

  A phthalimide-based fluorescent probe for H₂S with a large Stokes shift has been developed. This probe displayed good selectivity and high sensitivity. Imaging intracellular H₂S by using this probe was successfully achieved in living cells.

  已开发出一种基于邻苯二甲酰亚胺的具有较大斯托克斯位移的荧光探针，该探针显示出良好的选择性和高灵敏度。利用该探针成功在活细胞中实现了成像细胞内的H₂S。
• A new ESIPT-based fluorescent probe for highly selective and sensitive detection of hydrogen sulfide and its application in live-cell imaging
  作者：Bo Chen、Jing Huang、Huiqing Geng、Lingli Xuan、Tengfei Xu、Xin Li、Yifeng Han

  DOI：10.1039/c6nj03355e

  日期：——

  A new excited-state intramolecular proton transfer (ESIPT) based fluorescent probe for the detection of hydrogen sulfide has been reasonably designed and developed. The probe operates by H2S-mediated reduction of hydroxylamine to amine and exhibits high selectivity and sensitivity under mild conditions. Furthermore, the probe was successfully used for fluorescence imaging of H2S in living cells.

  一种新型的基于激发态分子内质子转移（ESIPT）的荧光探针可用于检测硫化氢。该探针通过H 2 S介导的羟胺还原为胺，在温和条件下显示出高选择性和灵敏度。此外，该探针已成功用于活细胞中H 2 S的荧光成像。
• A novel ESIPT-based fluorescent chemodosimeter for Hg²⁺ detection and its application in live-cell imaging
  作者：Jing Huang、Bo Chen、Baocheng Zhou、Yifeng Han

  DOI：10.1039/c7nj03789a

  日期：——

  high selectivity and sensitivity in an almost pure aqueous solution (containing only 1% DMSO) with a low detection limit of 1.5 ppb. Furthermore, the probe was successfully used for the fluorescence imaging of Hg2+ in live cells.

  合理设计和开发了一种新型的基于激发态的分子内质子转移（ESIPT）的荧光化学测厚仪，用于检测Hg 2+。该探针通过硫代邻苯二甲酰亚胺经汞促进的特定脱硫反应而运行，在几乎纯净的水溶液（仅含1％DMSO）中显示出高选择性和灵敏度，检测限低至1.5 ppb。此外，该探针已成功用于活细胞中Hg 2+的荧光成像。
• New phthalimide-methionine dyad-based fluorescence probes for reactive oxygen species: Singlet oxygen, hydrogen peroxide, and hypochlorite
  作者：Axel G. Griesbeck、Banu Öngel、Murat Atar

  DOI：10.1002/poc.3741

  日期：2017.9

  Different reactive oxygen species were detected by the molecular probes 1‐3 that were composed of the phthalimide fluorophore as reporter and a methionine‐derived thioether side‐chain as receptor part. The sulfoxides that were formed as the primary oxidation products show strong fluorescence in the blue‐green (430‐540 nm) spectral region. Self‐sensitized oxidation by singlet oxygen is in general inefficient

  通过分子探针1-3检测到不同的活性氧种类它们由邻苯二甲酰亚胺荧光团作为报告基因，由蛋氨酸衍生的硫醚侧链作为受体部分组成。形成为主要氧化产物的亚砜在蓝绿色（430-540 nm）光谱区域显示强荧光。单线态氧的自敏化氧化通常效率低下，表明被激发的探针分子会快速电子转移猝灭。用过氧化氢作为热氧化剂，转化为亚砜的速度很慢，但是可以通过添加钛（IV）催化剂来加速，而次氯酸盐作为氧化剂即使在未催化条件下也表现出更高的反应活性。由传感器1a通过光敏剂Rose Bengal的能量转移产生的单重态氧的速率常数> 10 7 M–1  s –1，硫醚氧化为亚砜的典型速率常数。