4-(2-异硫氰基乙基)苯酚 | 60114-04-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 4-(2-异硫氰基乙基)苯酚
• 英文名称: 2-(4-hydroxyphenyl)ethyl isothiocyanate
• 英文别名: 2-(p-hydroxyphenyl)ethyl isothiocyanate；4-(2-isothiocyanatoethyl)phenol；2-(4-Hydroxyphenyl)ethylisothiocyanate；4-hydroxyphenethylisothiocyanate
• CAS: 60114-04-7
• 化学式: C₉H₉NOS
• 分子量: 179.243
• InChiKey: DDWUOCNNMSTNMY-UHFFFAOYSA-N

物化性质

• 沸点：
  352.2±25.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)
• 保留指数：
  1805.9

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  64.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(2-异硫氰基乙基)苯酚 在 氢氧化钾 、 溴 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 3-hydroxy-5-[2-(4-hydroxyphenyl)ethylamino]isothiazole-4-carbonitrile
  参考文献：
  名称：

  Discovery of 3-hydroxy-4-carboxyalkylamidino-5-arylamino-isothiazoles as potent MEK1 inhibitors

  摘要：

  3-Hydroxy-4-carboxyalkylamidino-5-arylamino-isothiazoles were discovered as potent in vitro MEK1 inhibitors. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.05.019
• 作为产物：
  描述：

  二硫化碳 、 对羟基苯乙胺 在 双氧水 、 三乙胺 作用下， 生成 4-(2-异硫氰基乙基)苯酚
  参考文献：
  名称：

  Synthesis of Hydroxyalkyl Isothiocyanates

  摘要：

  氢氧烷基异硫氰酸酯通过将含有相应氢氧基初级胺、二硫化碳和催化量三乙胺的混合物在水溶性有机溶剂中，在0~10°C下与水相过氧化氢处理，获得高产率。

  DOI：

  10.1055/s-1997-5778

文献信息

• Fluorescent labeled nucleotide derivatives
  申请人：Shen G.-Y. Gene

  公开号：US20050227240A1

  公开（公告）日：2005-10-13

  Fluorescent labeled reporter compounds having a modified cyanine dye that is coupled to a nucleotide derivative through a linker are disclosed. The compounds are useful for nucleic acid sequence analysis. The fluorescent labeled reporter compounds are ring-locked cyanine dyes that are coupled to a nucleotide derivative, such as a modified DNA base, through a linker. These fluorescent labeled reporter compounds can be used as DNA chain-terminators in DNA synthesis to generate DNA fragments that are fluorescently-labeled at the 3′-terminal end of the DNA fragment.

  揭示了具有经过修饰的青霉素染料，通过连接剂与核苷酸衍生物偶联的荧光标记报告化合物。这些化合物对核酸序列分析很有用。这些荧光标记的报告化合物是环锁青霉素染料，通过连接剂与核苷酸衍生物（如修饰的DNA碱基）偶联。这些荧光标记的报告化合物可用作DNA合成中的DNA链终止剂，以生成在DNA片段的3'端荧光标记的DNA片段。
• Near-Infrared Heavy-Atom-Modified Fluorescent Dyes for Base-Calling in DNA-Sequencing Applications Using Temporal Discrimination
  作者：James H. Flanagan,、Clyde V. Owens、Sarah E. Romero、Emanuel Waddell、Shaheer H. Kahn、Robert P. Hammer、Steven A. Soper

  DOI：10.1021/ac980018g

  日期：1998.7.1

  A series of near-IR fluorescent dyes were prepared which contained an intramolecular heavy atom for altering the fluorescence lifetimes to produce a set of probes appropriate for base-calling in a single-lane DNA sequencing format. The heavy-atom modification consisted of an intramolecular halogen situated on a remote section of the chromophore in order to minimize the perturbation on the lifetimes and fluorescence quantum yields. In addition, the dye series possessed an isothiocyanate functional group to allow facile attachment to sequencing primers. The unconjugated dyes showed similar absorption and emission maxima (λabs = 765−768 nm; λem = 794−798 nm) as well as fluorescence quantum yields that were invariant, within experimental error, with the heavy atom. However, the lifetimes of these dyes were found to vary with the identity of the halogen substitution (I, τf = 947 ps; F, τf = 843 ps, measured in methanol), with an average variation within the dye series of 35 ps. The spectroscopic properties of the free dyes and the dyes conjugated to sequencing primers on the 5‘-end of the oligonucleotide were determined in a DNA-sequencing matrix (denaturing gels containing formamide). The results indicated slight differences in the fluorescence properties of the free dyes compared to those of the dye/primer conjugates in this particular matrix. Inspection of the ground-state absorption spectra showed significant aggregation for the free dyes in this solution, but the conjugated dyes exhibited no sign of aggregation due to the highly anionic nature of the oligonucleotide. The fluorescence lifetimes of the dye/primer conjugates demonstrated lifetimes which ranged from 735 to 889 ps, with an average variation of 51 ps, an adequate difference to allow facile discrimination of these dyes in DNA-sequencing conditions. In addition, the free solution electrophoretic mobilities of the native heavy-atom-modified dyes were found to be very similar. When the dye/primer conjugates were electrophoresed in a cross-linked polyacrylamide gel electrophoresis capillary column, they comigrated, indicating that, in single-lane sequencing applications, when utilizing these dyes, no postrun corrections would be required to correct for dye-dependent mobility shifts.

  我们制备了一系列近红外荧光染料，这些染料含有一个分子内重金属原子，可改变荧光寿命，从而产生一组适合单道 DNA 测序格式中碱基调用的探针。重原子修饰包括位于发色团偏远部分的分子内卤素，以尽量减少对荧光寿命和荧光量子产率的干扰。此外，染料系列还具有异硫氰酸酯官能团，可以方便地连接到测序引物上。非共轭染料显示出相似的吸收和发射最大值（λabs = 765-768 nm；λem = 794-798 nm）以及荧光量子产率，这些量子产率在实验误差范围内与重原子无关。然而，研究发现这些染料的寿命随卤素取代物的特性而变化（I，τf = 947 ps；F，τf = 843 ps，在甲醇中测量），染料系列内的平均变化为 35 ps。在 DNA 测序基质（含有甲酰胺的变性凝胶）中测定了游离染料和与寡核苷酸 5'- 端测序引物共轭的染料的光谱特性。结果表明，在这种特定基质中，游离染料的荧光特性与染料/引物共轭物的荧光特性略有不同。对基态吸收光谱的检测显示，游离染料在该溶液中出现了明显的聚集现象，但由于寡核苷酸的高阴离子性质，共轭染料没有出现聚集的迹象。染料/引物共轭物的荧光寿命从 735 到 889 ps 不等，平均变化为 51 ps，这种差异足以让这些染料在 DNA 测序条件下被轻松区分。此外，还发现原生重原子修饰染料的自由溶液电泳迁移率非常相似。当染料/原体共轭物在交联聚丙烯酰胺凝胶电泳毛细管柱中电泳时，它们会结合在一起，这表明在单道测序应用中，当使用这些染料时，无需进行运行后校正来纠正染料依赖性迁移率偏移。
• [EN] INHIBITORS OF MACROPHAGE MIGRATION INHIBITORY FACTOR<br/>[FR] INHIBITEURS DU FACTEUR D'INHIBITION DE LA MIGRATION DES MACROPHAGES
  申请人：HAMPTON MARK

  公开号：WO2010140902A1

  公开（公告）日：2010-12-09

  The invention provides the use of isothiocyanate and isoselenocyanate compounds for treating diseases and conditions mediated by MIF.

  本发明提供了使用异硫氰酸盐和异硒氰酸盐化合物来治疗由MIF介导的疾病和病症的方法。
• Short-warp peptide dye conjugate as contrast agent for optical diagnostic
  申请人：Licha Kai

  公开号：US20060036072A1

  公开（公告）日：2006-02-16

  The invention relates to compounds for tumor diagnosis that consist of conjugates of dyes with short-chain peptides, which are derived from vaso-active intestinal peptide, somatostatin or neurotensin, the use of these compounds as optical diagnostic agents, and diagnostic agents that contain these compounds.

  本发明涉及一种用于肿瘤诊断的化合物，其由染料与短链肽的结合物组成，所述短链肽源自于血管活性肠肽、生长抑素或神经紧张素，所述化合物用作光学诊断剂，并且包含这些化合物的诊断剂。
• Kurzkettige Peptid-Farbstoffkonjugate als Kontrastmittel für die optische Diagnostik
  申请人：INSTITUT FÜR DIAGNOSTIKFORSCHUNG GmbH AN DER FREIEN UNIVERSITÄT BERLIN

  公开号：EP1281405A2

  公开（公告）日：2003-02-05

  Die Erfindung betrifft Verbindungen zur Tumordiagnostik, bestehend aus Konjugaten von Farbstoffen mit kurzkettigen Peptiden, die vom vasoaktiven intestinalen Peptid, vom Somatostatin oder vom Neurotensin abgeleitet sind, die Verwendung dieser Verbindungen als optische Diagnostika, und diese Verbindungen enthaltende diagnostische Mittel.

  本发明涉及用于肿瘤诊断的化合物，包括染料与源自血管活性肠肽、体生长抑素或神经紧张素的短链肽的共轭物，这些化合物作为光学诊断的用途，以及含有这些化合物的诊断剂。