3-(1-hydroxypentyl)thiophene | 143581-97-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 3-(1-hydroxypentyl)thiophene
• 英文别名: 1-Thiophen-3-ylpentan-1-ol
• CAS: 143581-97-9
• 化学式: C₉H₁₄OS
• 分子量: 170.276
• InChiKey: RGCIBLOIRFHCKA-UHFFFAOYSA-N

物化性质

• 沸点：
  268.1±15.0 °C(Predicted)
• 密度：
  1.067±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  48.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(1-hydroxypentyl)thiophene 在 chromium(VI) oxide 作用下， 生成 1-(3-噻吩基)-1-戊酮
  参考文献：
  名称：

  Bandgap control through reduction of bond length alternation in bridged poly(diethienylethylene)s

  摘要：

  一项新型刚性双噻吩乙烯的X射线结构分析显示，观察到的HOMO-LUMO间隙的缩小是由于键长交替的放松所致。

  DOI：

  10.1039/a607890g
• 作为产物：
  描述：

  3-噻吩甲醛 、 溴丁基-镁 生成 3-(1-hydroxypentyl)thiophene
  参考文献：
  名称：

  Bandgap control through reduction of bond length alternation in bridged poly(diethienylethylene)s

  摘要：

  一项新型刚性双噻吩乙烯的X射线结构分析显示，观察到的HOMO-LUMO间隙的缩小是由于键长交替的放松所致。

  DOI：

  10.1039/a607890g

文献信息

• Synthesis and Carbonic Anhydrase Inhibitory Activity of 4-Substituted 2-Thiophenesulfonamides
  作者：Judy M. Holmes、Gary C. M. Lee、Mercy Wijono、Robert Weinkam、Larry A. Wheeler、Michael E. Garst

  DOI：10.1021/jm00037a015

  日期：1994.5

  A series of 4-substituted 2-thiophenesulfonamides was prepared from 3-thiophenecarboxaldehyde using metalation chemistry developed for 3-furaldehyde. Several of these compounds inhibit carbonic anhydrase II in vitro at concentrations of less than 10 nM. In addition, none of these compounds exhibit sensitization potential as determined from in vitro measurement of cysteine reactivity.

  使用针对3-呋喃醛开发的金属化化学方法，从3-噻吩甲醛中制备了一系列4-取代的2-噻吩磺酰胺。这些化合物中的几种在体外以小于10 nM的浓度抑制碳酸酐酶II。另外，这些化合物均未显示出由体外半胱氨酸反应性测定所确定的致敏潜力。
• Side-chain effects on the fragmentation behaviour of alkylthiophenes
  作者：D. Lange、H. Budzikiewicz

  DOI：10.1002/oms.1210290807

  日期：1994.8

  AbstractThe processes leading to the fragment ions formed from alkylthiophene molecule ions by benzylic cleavage without and with transfer of one hydrogen from the side‐chain to the ring and the influence of additional methyl groups on the relative importance of these two fragmentation reactions were investigated.
• A remarkable effect of ionic liquids in transition-metal-free aerobic oxidation of benzylic alcohols
  作者：Yoshiro Oda、Koji Hirano、Tetsuya Satoh、Susumu Kuwabata、Masahiro Miura

  DOI：10.1016/j.tetlet.2011.08.053

  日期：2011.10

  The transition-metal-free aerobic oxidation of benzylic alcohols is uniquely accelerated by a 1-butyl-3-methylimidazolium hexafluorophosphate (BMI-PF(6))/PhCF(3) biphasic system and Cs(2)CO(3) to afford the corresponding ketones in good yields. The reaction system is also applicable to an oxidative cross-esterification of primary benzyl alcohols with a higher aliphatic alcohol. (C) 2011 Elsevier Ltd. All rights reserved.
• Bridged Dithienylethylenes as Precursors of Small Bandgap Electrogenerated Conjugated Polymers
  作者：Philippe Blanchard、Hugues Brisset、Bertrand Illien、Amédée Riou、Jean Roncali

  DOI：10.1021/jo9623447

  日期：1997.4.1

  Bridged dithienylethylenes (DTEs) bearing solubilizing alkyl chains at various positions (2-5) have been synthesized by McMurry dimerization of cyclopenta[b]thiophen-6-ones. In order to introduce alkyl substituents at different positions of the DTE molecule, the precursor ketones have been prepared by different strategies based on a combination of Mannich or Wittig-Horner reaction and Friedel-Craft intramolecular cyclization. The position and the length of the alkyl substituents exert a strong effect on the ability of the precursor to undergo electrochemical polymerization. Thus, whereas substitution at the alpha-position of the ethylene linkage (3) results in a rapid inhibition of electropolymerization, introduction of alkyl chains at the beta-position (4, 5) greatly improves the efficiency of the polymerization process. The analysis of the electrochemical and optical properties of the polymers shows that rigidification of the DTE molecule leads to a significant decrease of the oxidation potential and bandgap. A comparative analysis of DTE and its bridged analogues by means of X-ray diffraction reveals, in agreement with experimental and theoretical results, that the observed reduction of both the HOMO-LUMO gap of the precursor and the bandgap of the corresponding polymers are related to a relaxation of bond length alternation in the DTE moiety.