3-(3-bromopropoxy)-4-methylthiophene | 514195-85-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(3-bromopropoxy)-4-methylthiophene
• 英文别名: 3-(3-Bromopropoxy)-4-methylthiophene
• CAS: 514195-85-8
• 化学式: C₈H₁₁BrOS
• 分子量: 235.145
• InChiKey: AILWNUDVELCMFR-UHFFFAOYSA-N

物化性质

• 沸点：
  287.5±30.0 °C(Predicted)
• 密度：
  1.421±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  37.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,2-二甲基咪唑 、 3-(3-bromopropoxy)-4-methylthiophene 以 乙腈 为溶剂， 反应 48.0h， 以80%的产率得到
  参考文献：
  名称：

  基于用于碘化物特异性检测的阳离子聚噻吩衍生物的新型比色和荧光化学传感器

  摘要：

  阴离子与新的水溶性、阳离子、亲和变色聚（3-烷氧基-4-甲基噻吩）衍生物之间的静电相互作用为碘离子的选择性光学检测方法（比色法或荧光法）提供了一种新工具。

  DOI：

  10.1021/ja028765p
• 作为产物：
  描述：

  3-溴-4-甲基噻吩 在 sodium hydrogen sulfate 、 copper(I) bromide 作用下， 以 N-甲基吡咯烷酮 、 甲醇 、 甲苯 为溶剂， 反应 72.0h， 生成 3-(3-bromopropoxy)-4-methylthiophene
  参考文献：
  名称：

  Fluorescence and colorimetric detection of ATP based on a strategy of self-promoting aggregation of a water-soluble polythiophene derivative

  摘要：

  基于一种自促聚集策略，开发了一种用于检测ATP的敏感荧光和比色双模探针，该探针是一种带有蒽基团的阳离子聚噻吩衍生物，侧链中的检测限值低至10⁻⁹ M。

  DOI：

  10.1039/c5cc01713k

文献信息

• Water-Soluble Conjugated Polymer as a Fluorescent Probe for Monitoring Adenosine Triphosphate Level Fluctuation in Cell Membranes during Cell Apoptosis and in Vivo
  作者：Binghuan Huang、Zhirong Geng、Shihai Yan、Zan Li、Jun Cai、Zhilin Wang

  DOI：10.1021/acs.analchem.7b01212

  日期：2017.9.5

  shows low toxicity to live cells and excellent photostability in cell membranes. PMTPP was practically utilized for real-time monitoring of ATP levels in the cell membrane through fluorescence microscopy. We have demonstrated that the ATP levels in cell membranes increased during the apoptotic cell death process. The probe was also capable of imaging ATP levels in living mice.

  三磷酸腺苷（ATP）被用作细胞中的能源，并且在各种细胞事件中起着至关重要的作用。细胞膜是活细胞细胞质的保护性屏障，并参与许多重要的生物学过程。已经成功开发了许多用于ATP的荧光探针，但是这些探针中很少有一种能在凋亡细胞死亡过程中可视化细胞膜中ATP的水平波动。在这里，我们报告了一种新型的水溶性阳离子聚噻吩衍生物的合成，该衍生物可用作检测细胞膜中ATP的荧光传感器。聚（（3-（（4-甲基噻吩-3-基氧基）丙基）三苯基phenyl氯化物）（PMTPP）表现出高灵敏度和对ATP的良好选择性，检出限为27 nM。该聚合物对活细胞毒性低，在细胞膜中具有出色的光稳定性。PMTPP实际上用于通过荧光显微镜实时监测细胞膜中ATP的水平。我们已经证明在凋亡细胞死亡过程中细胞膜中的ATP水平增加。该探针还能够对活体小鼠的ATP水平进行成像。
• Fluorescence Sensing of Phytate in Water Using an Isothiouronium-attached Polythiophene
  作者：Tsuyoshi Minami、Yuji Kubo

  DOI：10.1002/asia.200900444

  日期：2010.3.1

  438 nm) show an absorption band at 438 nm and fluorescence at 546 nm, with 1.2 % fluorescence quantum yield when fluorescein was used as a reference. The pH‐dependent absorption spectra at varying pH, indicates that aggregation starts at neutral conditions. At pH 5.5, 1poly exhibits a significant quenching in the fluorescence upon the addition of phytate (IP6), as a plausible analyte. This response

  水溶性异硫脲连接的聚噻吩（1个聚）通过氧化聚合首次制备3-（3-（ñ - （2-甲氧基乙氧基）乙基- ñ甲基小号-isothiouronio）丙氧基-4-甲基噻吩（1）和FeCl 3的凝胶渗透色谱分析使我们估计数均分子量（M n）和多分散指数（PDI）为5.68×10 5和1.4。当使用荧光素作参比时，聚合物（在438 nm激发）在438 nm处显示吸收带，在546 nm处显示荧光，荧光量子产率为1.2％。在不同pH值下pH依赖的吸收光谱表明，聚集是在中性条件下开始的。在pH 5.5时，1多聚体在添加肌醇六磷酸酯（IP 6）时，在荧光上表现出明显的猝灭，这是一种可行的分析物。这个响应比在其它阴离子诸如腺苷5-三磷酸（ATP），焦磷酸（PPI）的情况下，更高的顺式，顺式-1,3,5-环己三醇三磷酸（CTP 3）和H 2 PO 4 -。从SEM测量可以推断出，植酸引起的光谱变化已基于聚合物的π堆积聚集进行了解释。
• Self-Assembly of Supramolecular Chiral Insulated Molecular Wire
  作者：Chun Li、Munenori Numata、Ah-Hyun Bae、Kazuo Sakurai、Seiji Shinkai

  DOI：10.1021/ja050168q

  日期：2005.4.1

  Supramolecular chiral insulated molecular wire was constructed by self-assembly of a neutral one-dimensional schizophyllan host and a water-soluble polythiophene guest. The work presented here will not only open a door to a new application of polysaccharides but also provide an important clue to prepare stable supramolecular insulated molecular wires with one-handed helical structure.
• Selective anion-induced helical aggregation of chiral amphiphilic polythiophenes with isothiouronium-appended pendants
  作者：Tsuyoshi Minami、Yuji Kubo

  DOI：10.1080/10610278.2010.506546

  日期：2011.1.1

  An optically active isothiouronium-attached polythiophene 1poly has been prepared for the first time by oxidative polymerisation of (S)-3-(3-(N-(2-(2-methoxyethoxy)ethyl)-N-(1-phenylethyl)-S-isothiouronio)propoxy)-4-methylthiophene 1 with FeCl3. The analysis carried out using gel-permeation chromatography allows us to estimate the number average molecular weight (Mn) and the polydispersity index as 5.53x105 and 1.4, respectively. Although the polymer showed an absorption band at 420nm with circular dichroism (CD) silence in H2O-MeOH (1:1, v/v) at 25 degrees C, the addition of anions as a chemical stimulus was found to cause not only a bathochromic shift but also a split-type-induced CD (ICD) in the -* transition region. This phenomenon is anion selective; the most enhanced ICD spectra were obtained when hydrophobic anions such as [image omitted] were added to the solution. As inferred from field emission-scanning electron microscopy observation, the anion-ICD spectra arose from chiral aggregation of the polymer, which was effected by solvophobic effect via the exchange with hydrophobic anions at isothiouronium pendants. Solvent polarity and temperature dependencies on the chirality induction were investigated, the obtained results suggested that the dynamic helical aggregation of the polythiophene backbone is based on planar interchain interactions.
• Fluorescence and colorimetric detection of ATP based on a strategy of self-promoting aggregation of a water-soluble polythiophene derivative
  作者：Dandan Cheng、Yandong Li、Jing Wang、Yujiao Sun、Lu Jin、Chenxi Li、Yan Lu

  DOI：10.1039/c5cc01713k

  日期：——

  A sensitive fluorescent and colorimetric dual-modal probe for the detection of ATP has been developed based on a strategy of self-promoting aggregation of a cationic polythiophene derivative bearing anthracene groups in the side chain with a detection limit as low as 10⁻⁹ M.

  基于一种自促聚集策略，开发了一种用于检测ATP的敏感荧光和比色双模探针，该探针是一种带有蒽基团的阳离子聚噻吩衍生物，侧链中的检测限值低至10⁻⁹ M。