5-iodo-2,3-dihydrobenzo[b]thiophene | 1449384-45-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 5-iodo-2,3-dihydrobenzo[b]thiophene
• 英文别名: 2,3-dihydro-5-iodobenzo[b]thiophene；Benzo[b]thiophene, 2,3-dihydro-5-iodo-；5-iodo-2,3-dihydro-1-benzothiophene
• CAS: 1449384-45-5
• 化学式: C₈H₇IS
• 分子量: 262.114
• InChiKey: JLAPUCHSBVVNLE-UHFFFAOYSA-N

物化性质

• 沸点：
  302.7±41.0 °C(Predicted)
• 密度：
  1.871±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-iodo-2,3-dihydrobenzo[b]thiophene 在 copper(l) iodide 、 四(三苯基膦)钯 、 四丁基氟化铵 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 反应 8.5h， 生成 1,2-bis(2,3-dihydrobenzo[b]thien-5-yl)ethyne
  参考文献：
  名称：

  Single-Molecule Conductance of Functionalized Oligoynes: Length Dependence and Junction Evolution

  摘要：

  We report a combined experimental and theoretical investigation of the length dependence and anchor group dependence of the electrical conductance of a series of oligoyne molecular wires in single-molecule junctions with gold contacts. Experimentally, we focus on the synthesis and properties of diaryloligoynes with n = 1, 2, and 4 triple bonds and the anchor dihydrobenzo[b]thiophene (BT). For comparison, we also explored the aurophilic anchor group cyano (CN), amino (NH2), thiol (SH), and 4-pyridyl (PY). Scanning tunneling microscopy break junction (STM-BJ) and mechanically controllable break junction (MCBJ) techniques are employed to investigate single-molecule conductance characteristics. The BT moiety is superior as compared to traditional anchoring groups investigated so far. BT-terminated oligoynes display a 100% probability of junction formation and possess conductance values which are the highest of the oligoynes studied and, moreover, are higher than other conjugated molecular wires of similar length. Density functional theory (DFT)-based calculations are reported for oligoynes with n = 1-4 triple bonds. Complete conductance traces and conductance distributions are computed for each family of molecules. The sliding of the anchor groups leads to oscillations in both the electrical conductance and the binding energies of the studied molecular wires. In agreement with experimental results, BT-terminated oligoynes are predicted to have a high electrical conductance. The experimental attenuation constants beta(H) range between 1.7 nm(-1) (CN) and 3.2 nm(-1) (SH) and show the following trend: beta(H)(CN) < beta(H)(NH2) < beta(H)(BT) < beta(H)(PY) approximate to beta(H)(SH). DFT-based calculations yield lower values, which range between 0.4 nm(-1) (CN) and 2.2 nm(-1) (PY).

  DOI：

  10.1021/ja4015293
• 作为产物：
  描述：

  5-bromo-2,3-dihydrobenzo[b]thiophene 在 正丁基锂 、 碘 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 7.0h， 以89%的产率得到5-iodo-2,3-dihydrobenzo[b]thiophene
  参考文献：
  名称：

  Single-Molecule Conductance of Functionalized Oligoynes: Length Dependence and Junction Evolution

  摘要：

  We report a combined experimental and theoretical investigation of the length dependence and anchor group dependence of the electrical conductance of a series of oligoyne molecular wires in single-molecule junctions with gold contacts. Experimentally, we focus on the synthesis and properties of diaryloligoynes with n = 1, 2, and 4 triple bonds and the anchor dihydrobenzo[b]thiophene (BT). For comparison, we also explored the aurophilic anchor group cyano (CN), amino (NH2), thiol (SH), and 4-pyridyl (PY). Scanning tunneling microscopy break junction (STM-BJ) and mechanically controllable break junction (MCBJ) techniques are employed to investigate single-molecule conductance characteristics. The BT moiety is superior as compared to traditional anchoring groups investigated so far. BT-terminated oligoynes display a 100% probability of junction formation and possess conductance values which are the highest of the oligoynes studied and, moreover, are higher than other conjugated molecular wires of similar length. Density functional theory (DFT)-based calculations are reported for oligoynes with n = 1-4 triple bonds. Complete conductance traces and conductance distributions are computed for each family of molecules. The sliding of the anchor groups leads to oscillations in both the electrical conductance and the binding energies of the studied molecular wires. In agreement with experimental results, BT-terminated oligoynes are predicted to have a high electrical conductance. The experimental attenuation constants beta(H) range between 1.7 nm(-1) (CN) and 3.2 nm(-1) (SH) and show the following trend: beta(H)(CN) < beta(H)(NH2) < beta(H)(BT) < beta(H)(PY) approximate to beta(H)(SH). DFT-based calculations yield lower values, which range between 0.4 nm(-1) (CN) and 2.2 nm(-1) (PY).

  DOI：

  10.1021/ja4015293

文献信息

• Controlling and Observing Sharp-Valleyed Quantum Interference Effect in Single Molecular Junctions
  作者：Bing Huang、Xu Liu、Ying Yuan、Ze-Wen Hong、Ju-Fang Zheng、Lin-Qi Pei、Yong Shao、Jian-Feng Li、Xiao-Shun Zhou、Jing-Zhe Chen、Shan Jin、Bing-Wei Mao

  DOI：10.1021/jacs.8b10450

  日期：2018.12.19

  The ability to control over the quantum interference (QI) effect in single molecular junctions is attractive in the application of molecular electronics. Herein we report that the QI effect of meta-benzene based molecule with dihydrobenzo[ b]thiophene as the anchoring group ( meta-BT) can be controlled by manipulating the electrode potential of the junctions in electrolyte while the redox state of

  控制单分子结中的量子干涉 (QI) 效应的能力在分子电子学的应用中很有吸引力。在本文中，我们报道了以二氢苯并 [b] 噻吩为锚定基团 (meta-BT) 的间苯基分子的 QI 效应可以通过操纵电解质中结的电极电位来控制，而分子的氧化还原状态则不会改变。随着电极电位的变化，间位 BT 的电导变化超过 2 个数量级，范围从 <10-6.0 到 10-3.3 G0，而上限值甚至大于对位 BT（基于对苯的电导）的电导变化。具有二氢苯并[b]噻吩锚定基团的分子）。这种现象归因于在电极电位控制下分子和电极之间的能级排列的移动。计算预测了单分子结的传递函数和分子存在时Au表面的功函数，理论与实验吻合良好，均显示出尖谷特征对元的破坏性QI效应。 BT。目前的工作表明，QI 效应可以通过电化学门控进行调节，而不会改变分子的氧化还原状态，这为实现有效的分子开关提供了一种可行的方法。并且在理论和实验之间发现了良好的一致性，两者都显示了对元
• Radical-Enhanced Charge Transport in Single-Molecule Phenothiazine Electrical Junctions
  作者：Junyang Liu、Xiaotao Zhao、Qusiy Al-Galiby、Xiaoyan Huang、Jueting Zheng、Ruihao Li、Cancan Huang、Yang Yang、Jia Shi、David Zsolt Manrique、Colin J. Lambert、Martin R. Bryce、Wenjing Hong

  DOI：10.1002/anie.201707710

  日期：2017.10.9

  Single-molecule conductances of phenothiazine radicals have been measured using the mechanically controllable break junction technique. Triggered by an acid oxidant, the radical cation of phenothiazine enhances the charge-transport property by up to 200 times with high stability and high junction formation probability at room temperature, which leads to promising applications in single-molecule electronics

  吩噻嗪自由基的单分子电导率已使用机械可控的断裂连接技术进行了测量。吩噻嗪的自由基阳离子受酸氧化剂的触发，在室温下具有高稳定性和高结形成几率，可将电荷传输性能提高200倍，这在单分子电子学和自旋电子学中具有广阔的应用前景。
• Syntheses and Structures of Buta-1,3-Diynyl Complexes from “on Complex” Cross-Coupling Reactions
  作者：Marie-Christine Oerthel、Dmitry S. Yufit、Mark A. Fox、Martin R. Bryce、Paul J. Low

  DOI：10.1021/om501186c

  日期：2015.6.8

  to provide the octa-1,3,5,7-tetrayndiyl complex Ru(PPh3)2Cp}2(μ-C≡CC≡CC≡CC≡C) (6). Crystallographically determined molecular structures are reported for five complexes (4a, 4b, 4d, 5, and 6). Quantum chemical calculations indicate that the HOMOs are mainly located on the C4–C6H4–C4 and C8 bridges for 5 and 6, respectively, while spectroelectrochemical (UV–vis–NIR and IR) studies on 6 establish that

  Pd（PPh 3）4 / CuI催化Ru（C≡CC≡CH）（PPh 3）2 Cp（2）与芳基碘化物Ar–I（3，Ar = C 6 H 4 CN-4（a）; C 6 H 4 Me-4（b）; C 6 H 4 OMe-4（c）; 2,3-二氢苯并[ b ]噻吩（d）; C 5 H 4 N（e））在二异丙胺，在惰性气氛下，生成取代的buta-1,3-diynyl络合物Ru（C≡CC≡CAr）（PPh3）2 Cp（4a – e），产量中等至良好。该方法允许快速制备一系列芳基丁1，3-二炔基配体的金属配合物，而无需事先合成各个丁1，3-二炔作为配体前体。2与一半当量的1,4-二碘苯的类似反应得到双金属衍生物Ru（PPh 3）2 Cp} 2（μ-C≡CC≡C-1,4- C6 H 4 - C≡CC≡ C）（5）。在大气氧的存在下，二炔基试剂2发生均偶联，以提供octa-1,3,5,7-四炔二基络合物Ru（PPh
• [EN] PYRIMIDINE-CONTAINING TRI-SUBSTITUTED IMIDAZOLE COMPOUND AND APPLICATION THEREOF<br/>[FR] COMPOSÉ D'IMIDAZOLE TRI-SUBSTITUÉ CONTENANT DE LA PYRIMIDINE ET UTILISATION ASSOCIÉE<br/>[ZH] 含嘧啶的三取代咪唑类化合物及其应用
  申请人：GUANGZHOU BEBETTER MEDICINE TECH CO LTD

  公开号：WO2020192302A1

  公开（公告）日：2020-10-01

  公开了一种具有式（I）所示结构的含嘧啶的三取代咪唑类化合物及其应用。该类化合物可以有效抑制包括EGFR ex19del/T790M/C797S和L858R/T790M/C797S在内的EGFR C797S突变，同时对包括单点突变L858R、ex19del和双点突变如L858R/T790M，ex19del/T790M等也有较高抑制活性，并且，这类化合物对野生型EGFR抑制作用弱，即具有很好的选择性。该类化合物有潜力成为用作携带EGFR C797S突变的恶性肿瘤，尤其是非小细胞肺癌（NSCLC）治疗的药物，有较大的应用价值。
• OPIOID RECEPTOR LIGANDS AND METHODS OF USING AND MAKING SAME
  申请人：Trevena, Inc.

  公开号：EP2688403B1

  公开（公告）日：2017-05-31