2-溴-5-(4-甲氧基苯基)噻吩 | 54095-24-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 2-溴-5-(4-甲氧基苯基)噻吩
• 英文名称: 2-bromo-5-(4-methoxyphenyl)thiophene
• CAS: 54095-24-8
• 化学式: C₁₁H₉BrOS
• 分子量: 269.162
• InChiKey: JERXMXIBBDYMDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  37.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  2-溴-5-(4-甲氧基苯基)噻吩 在 正丁基锂 、 硼酸三乙酯 、 盐酸 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 生成 [5-(4-甲氧基苯基)-2-噻吩基]硼酸
  参考文献：
  名称：

  New Insights into the SAR and Binding Modes of Bis(hydroxyphenyl)thiophenes and -benzenes: Influence of Additional Substituents on 17β-Hydroxysteroid Dehydrogenase Type 1 (17β-HSD1) Inhibitory Activity and Selectivity

  摘要：

  17 beta-Hydroxystcroid dehydrogenase type 1 (17 beta-HSD1) is responsible for the catalytic reduction of weakly active E1 to highly potent E2. E2 stimulates the proliferation of hormone-dependent diseases via activation of the estrogen receptor alpha (ER alpha). Because of the overexpression of 17 beta-HSD1 in mammary tumors, this enzyme should be an attractive target for the treatment of estrogen-dependent pathologies. Recently, we have reported on a series of potent 17 beta-HSD1 inhibitors: bis(hydroxyphenyl) azoles, thiophenes, and benzenes. In this paper, different substituents are introduced into the core structure and the biological properties of the corresponding inhibitors are evaluated. Computational methods and analysis of different X-rays of 17 beta-HSD1 lead to identification of two different binding modes for these inhibitors. The fluorine compound 23 exhibits an IC50 of 8 nM and is the most potent nonsteroidal inhibitor described so far. It also shows a high selectivity (17 beta-HSD2, ER alpha) and excellent pharmacokinetic properties after peroral application to rats.

  DOI：

  10.1021/jm901195w
• 作为产物：
  描述：

  2-(4-甲氧苯基)噻吩 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以65%的产率得到2-溴-5-(4-甲氧基苯基)噻吩
  参考文献：
  名称：

  咔唑基染料敏化太阳能电池中噻吩间隔物位置对光物理、电化学和光伏性能的影响

  摘要：

  报道了五种以咔唑部分为电子供体的新型无金属有机敏化剂在染料敏化太阳能电池 (DSSC) 中的合成、光物理和电化学性能以及光伏性能。该化合物在不同位置包含噻吩和作为电子受体的氰基丙烯酸单元。噻吩部分的位置影响光物理和电化学性质，导致在 AM 1.5 太阳能条件（100 mW cm-2）下的转换效率为 1.44% 至 4.57%。当噻吩同时位于供体和受体位点时，性能最佳，电子寿命最长。DSSC 显示短路电流 (Jsc) 为 8.59 mA/cm2，开路光电压 (Voc) 为 0.75 V，填充因子 (FF) 为 0.71。

  DOI：

  10.1002/ejoc.201600353

文献信息

• Rodlike 4,6-diamino-1,3,5-triazine derivatives, effect of the core length on mesophase behavior and their application as LE-LCD device
  作者：Xiaoping Tan、Qing Chang、Fawu Su、Yu Cao、Feng Liu、Xiaohong Cheng

  DOI：10.1016/j.molliq.2021.117879

  日期：2022.1

  small/wide angle X-ray scattering, grazing incident small-angle X-ray scattering as well as molecular dynamics simulation, the results indicate that molecular curvature is critical to self-assembly structures. Moreover, the prerequisite for the formation of the CubI/Im3¯m phase is intermediate molecular curvature on the surface of the micelle to allow the intercalation of the alkyl chains. Finally,

  已经合成了三个系列不同核心长度的二氨基三嗪衍生物，并系统研究了结构变化和温度对其中间相行为的影响。专注于 CubI/Im3 ̄m 相的形成，发现了多个 2D/3D 相。通过偏振光学显微镜、小/广角 X 射线散射、掠入射小角 X 射线散射以及分子动力学模拟证实，结果表明分子曲率对自组装结构至关重要。此外，形成 CubI/Im3 ̄m 相的先决条件是胶束表面的中等分子曲率，以允许烷基链插层。最后，初步证明了发光液晶显示器 （LE-LCD） 器件等化合物的潜力。
• Selective Mechanochemical Monoarylation of Unbiased Dibromoarenes by <i>in Situ</i> Crystallization
  作者：Tamae Seo、Koji Kubota、Hajime Ito

  DOI：10.1021/jacs.0c01739

  日期：2020.6.3

  Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions of liquid, unbiased dibromoarenes under mechanochemical conditions selectively afford the monoarylated products. The lower reactivity of the crystalline monoarylated products rela-tive to the liquid starting materials should be attributed predom-inantly to the low diffusion efficiency of the former in the re-action mixture, which results in

  在机械化学条件下，钯催化的液体无偏二溴芳烃的 Suzuki-Miyaura 交叉偶联反应选择性地提供单芳基化产物。结晶单芳基化产物相对于液体原料的较低反应性主要归因于前者在反应混合物中的低扩散效率，这导致选择性单芳基化。本研究揭示了一种新方法，该方法使用固体中的原位相变来设计通过传统的基于溶液的合成难以实现的选择性有机转化。
• Liquid crystalline 2-thienyl-4,6-diamino-1,3,5-triazines exhibiting Im3̄m and Pm3̄n micellar cubic phases in an inverted sequence
  作者：Heng Dai、Xueyan Yang、Xiaoping Tan、Fawu Su、Xiaohong Cheng、Feng Liu、Carsten Tschierske

  DOI：10.1039/c3cc45467c

  日期：——

  Two micellar cubic phases with different structures were observed for the first time in the order Imm–Pmn in a thermotropic phase sequence of 4,6-diaminotriazine terminated rod-like liquid crystals upon increasing alkyl chain length or rising temperature.

  在4,6-二氨基三嗪末端的棒状液晶中，首次观察到两种不同结构的胶束立方相，按照Imm–Pmn的顺序出现在温度升高或烷基链长度增加的热赋形相序列中。
• A facile synthetic route for 2-pyridyl derivatives: direct preparation of a stable 2-pyridylzinc bromide and its copper-free and pd-catalyzed coupling reactions
  作者：Seung-Hoi Kim、Reuben D. Rieke

  DOI：10.1016/j.tetlet.2009.07.004

  日期：2009.9

  Direct preparation of 2-pyridylzinc bromide has been developed. Interestingly, the subsequent coupling reactions with acid chlorides have been carried out without any transition metal catalyst. 2-Pyridylaryl compounds, symmetrical and unsymmetrical 2,2′-bipyridines were also successfully obtained from palladium-catalyzed coupling reactions of 2-pyridylzinc bromide under mild conditions.

  已经开发了直接制备2-吡啶基溴化锌的方法。有趣的是，随后与酰氯的偶联反应已经在没有任何过渡金属催化剂的情况下进行了。还可以从钯催化的2-吡啶基溴化锌在温和条件下的偶联反应中成功获得2-吡啶基芳基化合物，对称和不对称的2,2'-联吡啶。
• 2-Pyridyl and 3-pyridylzinc bromides: direct preparation and coupling reaction
  作者：Seung-Hoi Kim、Reuben D. Rieke

  DOI：10.1016/j.tet.2010.02.061

  日期：2010.4

  A facile synthetic approach to the direct preparation of 2-pyridyl and 3-pyridylzinc bromides has been demonstrated using Rieke zinc with 2-bromopyridine and 3-bromopyridine, respectively. A variety of different electrophiles have been coupled with the resulting organozinc reagents to give the corresponding cross-coupling products in moderate to good yields.

  已证明使用Rieke锌分别与2-溴吡啶和3-溴吡啶直接合成2-吡啶基和3-吡啶基锌溴化物的简便合成方法。各种不同的亲电试剂已与所得的有机锌试剂偶联，以中等至良好的产率得到相应的交叉偶联产物。