2-溴-5-丁基噻吩 | 128619-83-0

• 物质功能分类: 医药中间体 - 杂环化合物 - 噻吩类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: 2-溴-5-丁基噻吩
• 英文名称: 2-bromo-5-butylthiophene
• CAS: 128619-83-0
• 化学式: C₈H₁₁BrS
• 分子量: 219.145
• InChiKey: BQPMOWMCGHVEDO-UHFFFAOYSA-N

物化性质

• 沸点：
  237.1±20.0 °C(Predicted)
• 密度：
  1.361±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-溴-5-丁基噻吩 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以95%的产率得到3-bromo-5-nbutylthiophene
  参考文献：
  名称：

  的Pd / C作为完全的区域选择性℃的催化剂？在温和条件下噻吩的H功能化

  摘要：

  通过在温和的反应条件下使用Pd / C作为不带配体或添加剂的非均相催化剂，可以实现噻吩和苯并[ b ]噻吩的完全C3选择性芳基化。该转化的实用性通过显着的官能团耐受性和反应对H 2 O和空气的不敏感性得到证明。该方法也适用于含氮和氧的杂环，产生相应的C2芳基化产物。三相试验以及汞中毒和热过滤试验表明，催化活性物质在性质上是异质的。

  DOI：

  10.1002/anie.201309305
• 作为产物：
  描述：

  2-正丁基噻吩 在 N-溴代丁二酰亚胺(NBS) 、 溶剂黄146 作用下， 以 氯仿 为溶剂， 生成 2-溴-5-丁基噻吩
  参考文献：
  名称：

  Nematic 2,5-disubstituted thiophenesElectronic supplementary information (ESI) available: extensive synthetic information. See http://www.rsc.org/suppdata/jm/b2/b202073b/

  摘要：

  制备了大量含有2,5-二取代噻吩环的新型液晶，并研究了它们的介晶行为，以系统地探讨不同形状、极化能力和极性的噻吩衍生物的分子结构与介晶性之间的关联。通过这些研究，我们合成了一类新型液晶，它们含有2,5-二取代噻吩环和末端链中的共轭反式碳-碳双键。这些新颖的噻吩衍生物是首批在室温下表现出向列相的含有2,5-二取代噻吩环的液晶。这使得弯曲形状分子的挠曲电系数能够首次在作者所知的情况下直接在室温下测量。许多这些新型噻吩具有高双折射率和高向列相清亮点，有可能作为液晶显示器中向列相混合物的成分。

  DOI：

  10.1039/b202073b

文献信息

• Synthesis and Characterization of Benzannelated Thienyl Oligomers
  作者：Pitchamuthu Amaladass、J. Arul Clement、Arasambattu K. Mohanakrishnan

  DOI：10.1002/ejoc.200800244

  日期：2008.8

  An array of 1,3-diarylbenzo[c]thiophenes have been synthesized by the ring-opening of lactones followed by thionation using Lawesson's reagent with concurrent intramolecular cyclization. Photophysical studies of the various benzo[c]thiophene analogues are presented. The results of a cyclic voltammetric investigation of the benzo[c]thiophenes are also reported.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451

  一系列 1,3-二芳基苯并 [c] 噻吩已通过内酯的开环合成，然后使用 Lawesson 试剂进行硫化并同时进行分子内环化。介绍了各种苯并 [c] 噻吩类似物的光物理研究。还报告了苯并 [c] 噻吩的循环伏安法研究结果。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
• Chromanes and their pharmaceutical compositions and methods
  申请人：Hoffmann-La Roche Inc.

  公开号：US05015661A1

  公开（公告）日：1991-05-14

  Racemic Compounds of the formula ##STR1## A is --C.tbd.C--R.sub.6, --CH.sub.2 --CH.sub.2 --R.sub.7 or ##STR2## R.sub.1 is hydrogen or lower alkanoyl, R.sub.2, R.sub.3, and R.sub.4 independently are hydrogen or lower alkyl, R.sub.5 is lower alkyl, R.sub.6 is a heteroaromatic radical or an aromatic radical selected from phenyl, naphthyl or phenanthryl, which aromatic radical may optionally be substituted by one or more substituents selected from chlorine, fluorine, lower alkyl, lower alkoxy, phenyl lower alkoxy, lower alkanoyl, lower alkanoyloxy, hydroxy-lower alkyl, carboxy, lower alkoxycarbonyl, hydroxyimino lower alkyl, amino, amino lower alkyl, mono- or di-lower alkylamino, mono- or di-lower alkylamino-lower alkyl, lower alkanoylamino, aminocarbonyl, lower alkylaminocarbonyl, lower dialkylaminocarbonyl, trifluoroacetylamino, trifluoromethyl, hydroxy, pyridyl, or on adjacent carbons can be ##STR3## wherein R' is hydrogen, lower alkanoyl, trifluoroacetyl and R" hydrogen or lower alkyl, R.sub.7 is a heteroaromatic radical or an aromatic radical selected from phenyl, naphthyl or phenanthryl, which aromatic radical may optionally be substituted by one or more substituents selected from chlorine, fluorine, lower alkyl, lower alkoxy, phenyl-lower alkoxy of 2-7 carbon atoms, lower alkanoyl, lower alkanoyloxy, hydroxy-lower alkyl, carboxy, lower alkoxycarbonyl, amino, amino-lower alkyl, mono- or di-lower alkylamino, mono- or di-lower alkylamino-lower alkyl, lower alkanoylamino, aminocarbonyl, lower alkylaminocarbonyl, lower dialkylaminocarbonyl, trifluoroacetylamino, trifluoromethyl, hydroxy or pyridyl, or on adjacent carbons can be ##STR4## wherein R' is hydrogen, lower alkanoyl, trifluoroacetyl and R" hydrogen or lower alkyl, R.sub.8, R.sub.9, R.sub.10, independently, are hydrogen, hydroxy, lower alkyl, lower alkoxy, hydroxy lower alkyl, fluorine, chlorine or lower alkanoyl provided that no more than one of R.sub.8, R.sub.9, and R.sub.10 is hydroxy, lower alkoxy, lower hydroxyalkyl, fluorine, chlorine or lower alkanoyl, and Y is CH or N, and their enantiomer and salts thereof are described. The compounds of formula I exhibit activity as inhibitors of 5-lipoxygenase and inhibit lipid peroxidation. They are, therefore, useful in the treatment of diseases caused or aggravated by excess oxidative metabolism of arachidonic acid via the 5-lipoxygenase pathway and in the treatment of inflammation, arthritis, allergies, asthma and psoriasis. The compounds of formula I can also be used to prevent peroxidation of lipids and thus protect lipid membranes from oxidative stress.

  公式为##STR1##的消旋化合物。其中A为--C.tbd.C--R.sub.6，--CH.sub.2 --CH.sub.2 --R.sub.7或##STR2##，R.sub.1为氢或较低的烷酰基，R.sub.2、R.sub.3和R.sub.4独立地为氢或较低的烷基，R.sub.5为较低的烷基，R.sub.6为异芳基或苯基，萘基或苯并芘基中选择的芳基，该芳基可以选择性地被氯、氟、较低烷基、较低烷氧基、苯基较低烷氧基、较低烷酰基、较低烷酰氧基、羟基较低烷基、羧基、较低烷氧羰基、羟基亚胺较低烷基、氨基、氨基较低烷基、单烷基氨基或二烷基氨基、单烷基氨基或二烷基氨基较低烷基、较低烷酰胺基、氨基羰基、较低烷基氨基羰基、较低二烷基氨基羰基、三氟乙酰氨基、三氟甲基、羟基、吡啶基或相邻碳上的可以是##STR3##，其中R'为氢、较低烷酰基、三氟乙酰基，R"为氢或较低烷基，R.sub.7为异芳基或苯基，选择自苯基、萘基或苯并芘基的芳基，该芳基可以选择性地被氯、氟、较低烷基、较低烷氧基、苯基较低烷氧基（碳原子数为2-7）、较低烷酰基、较低烷酰氧基、羟基较低烷基、羧基、较低烷氧羰基、氨基、氨基较低烷基、单烷基氨基或二烷基氨基、单烷基氨基或二烷基氨基较低烷基、较低烷酰胺基、氨基羰基、较低烷基氨基羰基、较低二烷基氨基羰基、三氟乙酰氨基、三氟甲基、羟基或吡啶基，或相邻碳上的可以是##STR4##，其中R'为氢、较低烷酰基、三氟乙酰基，R"为氢或较低烷基，R.sub.8、R.sub.9、R.sub.10独立地为氢、羟基、较低烷基、较低烷氧基、羟基较低烷基、氟、氯或较低烷酰基，但R.sub.8、R.sub.9和R.sub.10中不超过一个为羟基、较低烷氧基、较低羟基烷基、氟、氯或较低烷酰基，Y为CH或N，描述了它们的对映体和盐。公式I的化合物表现出作为5-脂氧酶抑制剂的活性，并抑制脂质过氧化。因此，它们在治疗由于花生四烯酸通过5-脂氧酶途径的过度氧化代谢引起或加重的疾病以及治疗炎症、关节炎、过敏、哮喘和牛皮癣方面是有用的。公式I的化合物还可用于预防脂质过氧化，从而保护脂质膜免受氧化应激的影响。
• Nematic 2,5-disubstituted thiophenesElectronic supplementary information (ESI) available: extensive synthetic information. See http://www.rsc.org/suppdata/jm/b2/b202073b/
  作者：Neil L. Campbell、Warren L. Duffy、Gareth I. Thomas、Janine H. Wild、Stephen M. Kelly、Kevin Bartle、Mary O'Neill、Vicky Minter、Rachel P. Tuffin

  DOI：10.1039/b202073b

  日期：2002.8.30

  A large number of new liquid crystals incorporating the 2,5-disubstituted thiophene ring have been prepared and their mesomorphic behaviour studied in order to systematically investigate the correlation between the molecular structure and mesomorphism of thiophene derivatives with different shapes, polarisability and polarity. As a consequence of these investigations we have prepared a new class of liquid crystals incorporating a 2,5-disubstituted thiophene ring and a conjugated trans-carbon–carbon double bond in the terminal chain. These novel thiophene derivatives are the first liquid crystals incorporating a 2,5-disubstituted thiophene ring to exhibit a nematic phase at room temperature. This enables the flexoelectric coefficients of a bent-shaped molecule to be measured directly and at room temperature for the first time to the authors' knowledge. Many of these new thiophenes exhibit a high birefringence and a high nematic clearing point and are of potential use as components of nematic mixtures in LCDs.

  制备了大量含有2,5-二取代噻吩环的新型液晶，并研究了它们的介晶行为，以系统地探讨不同形状、极化能力和极性的噻吩衍生物的分子结构与介晶性之间的关联。通过这些研究，我们合成了一类新型液晶，它们含有2,5-二取代噻吩环和末端链中的共轭反式碳-碳双键。这些新颖的噻吩衍生物是首批在室温下表现出向列相的含有2,5-二取代噻吩环的液晶。这使得弯曲形状分子的挠曲电系数能够首次在作者所知的情况下直接在室温下测量。许多这些新型噻吩具有高双折射率和高向列相清亮点，有可能作为液晶显示器中向列相混合物的成分。
• Synthesis of end-blocked thienyl oligomers incorporating benzo[c]thiophene
  作者：Arasambattu K. Mohanakrishnan、P. Amaladass、J. Arul Clement

  DOI：10.1016/j.tetlet.2006.11.178

  日期：2007.1

  A straightforward synthesis of end-capped bithienyl, quaterthienyl and sexithienyl systems incorporating benzo[c]thiophene units is presented.

  提出了结合有苯并[ c ]噻吩单元的封端的二苯基，四噻吩基和六噻吩基体系的直接合成方法。
• Synthesis and Properties of Butyl-Capped Dehydrothieno[14]annulenes and Their Conversion into Terthiophenes
  作者：Matthew J. O’Connor、Michael M. Haley

  DOI：10.1021/ol801451x

  日期：2008.9.18

  A series of butyl end-capped dehydrothieno[14]annulenes (DTAs) has been prepared. These compounds were further transformed into electron-rich terthiophenes (3TPs) by reaction with sodium sulfide. The DTA and 3TP macrocycles were compared qualitatively using UV-vis spectroscopy, and the latter were found to have lower energy absorptions. The conformations of these molecules were also examined by DFT-YFLP

  制备了一系列丁基封端的脱氢噻吩并[14]环戊烯（DTA）。通过与硫化钠反应，将这些化合物进一步转化为富含电子的三噻吩（3TP）。使用紫外可见光谱定性比较了DTA和3TP大环化合物，发现后者的能量吸收较低。还通过DFT-YFLP计算检查了这些分子的构象。