4-methoxy-3-iodo-1-tosyloxybenzene | 186134-37-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-methoxy-3-iodo-1-tosyloxybenzene
• 英文别名: 3-iodo-4-methoxyphenyl 4-methylbenzenesulfonate；3-iodo-4-methoxyphenyl tosylate；3-iodo-4-methoxyphenyl p-toluenesulfonate；3-Iodo-4-methoxyphenyl 4-methylbenzene-1-sulfonate；(3-iodo-4-methoxyphenyl) 4-methylbenzenesulfonate
• CAS: 186134-37-2
• 化学式: C₁₄H₁₃IO₄S
• 分子量: 404.225
• InChiKey: WLMDWDBFKZIMBH-UHFFFAOYSA-N

物化性质

• 沸点：
  490.8±45.0 °C(Predicted)
• 密度：
  1.646±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-methoxy-3-iodo-1-tosyloxybenzene 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium hydroxide 、 copper(l) iodide 、 potassium carbonate 、 三乙胺 、 叔丁醇 作用下， 以 丙酮 为溶剂， 反应 25.0h， 生成 [(2,5-二甲氧基苯基)乙炔基]三甲基硅烷
  参考文献：
  名称：

  供体和受体组对棒状 π 共轭系统的发光效率调节

  摘要：

  鉴于高效发光材料在化学、生物科学和材料科学中的重要性日益增加，我们研究了棒状低聚（对亚苯基乙炔）（OPE，三聚体到五聚体系统）的发光效率调节) 由供体和受体基团组成，因此它们在 460 nm 作为所需波长区域发出非常强烈的荧光（Phif 约为 1.0，log epsilon 约为 5）。这一目标是通过 MeO（供体）基团的侧向改性和 CN 取代的苯环或 CF3 取代的吡啶环（受体）对四聚对亚苯基乙炔基棒状分子（Phif = 0.96，λem = 458）的末端改性实现的nm，前者的 log epsilon = 4.96，Phif = 0.99，lambdaem = 459 nm，后者的 log epsilon = 4.92）。11 和 12 的高 Phif 值用 kr（辐射速率常数）和 kd（无辐射速率常数）来解释。首次发现Phif与Hammett sigma常数之间呈正斜率的线性关系。发现

  DOI：

  10.1021/ja051588i
• 作为产物：
  描述：

  对苯二酚 在 吡啶 、 potassium iodate 、 硫酸 、 碘 、 sodium hydride 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 生成 4-methoxy-3-iodo-1-tosyloxybenzene
  参考文献：
  名称：

  REGIOREGULAR COPOLYMERS AND METHODS FOR MAKING SAME

  摘要：

  本文描述了制备顺向规整的聚（芳基乙炔基）-聚（芳基乙烯基）及用于制备这些聚合物的单体的方法。顺向规整的聚（芳基乙炔基）-聚（芳基乙烯基）在电子领域等方面具有实用性。

  公开号：

  US20150094484A1

文献信息

• Light-Emitting Efficiency Tuning of Rod-Shaped π Conjugated Systems by Donor and Acceptor Groups
  作者：Yoshihiro Yamaguchi、Takahiro Tanaka、Shigeya Kobayashi、Tateaki Wakamiya、Yoshio Matsubara、Zen-ichi Yoshida

  DOI：10.1021/ja051588i

  日期：2005.7.1

  trimeric to pentameric systems) by donor and acceptor groups, so that they emit the very intense fluorescence (Phif approximately 1.0, log epsilon approximately 5) at 460 nm as the desired wavelength region. This goal was achieved by side modification by MeO (donor) groups and end modification by a CN-substituted benzene ring or CF3-substituted pyridine ring (acceptor) of tetrameric p-phenylene ethynylene

  鉴于高效发光材料在化学、生物科学和材料科学中的重要性日益增加，我们研究了棒状低聚（对亚苯基乙炔）（OPE，三聚体到五聚体系统）的发光效率调节) 由供体和受体基团组成，因此它们在 460 nm 作为所需波长区域发出非常强烈的荧光（Phif 约为 1.0，log epsilon 约为 5）。这一目标是通过 MeO（供体）基团的侧向改性和 CN 取代的苯环或 CF3 取代的吡啶环（受体）对四聚对亚苯基乙炔基棒状分子（Phif = 0.96，λem = 458）的末端改性实现的nm，前者的 log epsilon = 4.96，Phif = 0.99，lambdaem = 459 nm，后者的 log epsilon = 4.92）。11 和 12 的高 Phif 值用 kr（辐射速率常数）和 kd（无辐射速率常数）来解释。首次发现Phif与Hammett sigma常数之间呈正斜率的线性关系。发现
• Copper-Catalyzed Regioselective C-H Sulfonyloxylation of Electron-Rich Arenes with <i>p</i>-Toluenesulfonic Acid and Sulfonyloxylation of Aryl(mesityl)iodonium Sulfonates
  作者：He Huang、Yang Wu、Wen Zhang、Chun Feng、Bi-Qin Wang、Wan-Fei Cai、Ping Hu、Ke-Qing Zhao、Shi-Kai Xiang

  DOI：10.1021/acs.joc.7b00081

  日期：2017.3.17

  Copper-catalyzed regioselective C-H sulfonyloxylation of electron-rich arenes with p-toluenesulfonic acid has been developed. Electron-rich benzene derivatives and heteroarenes can undergo this C-H sulfonyloxylation reaction to generate aryl tosylates. Furthermore, sulfonyloxylation of aryl(mesityl)iodonium sulfonates has also been investigated. Both aryl(mesityl)iodonium tosylates and triflates can

  已经开发了用对甲苯磺酸的铜催化富电子芳烃的区域选择性CH磺酰氧基化。富电子的苯衍生物和杂芳烃可以经过此CH磺酰氧基化反应生成芳基甲苯磺酸酯。此外，还研究了芳基（间苯二甲氧基）碘鎓磺酸盐的磺酰氧基化。芳基（间苯二甲氧基）碘鎓甲苯磺酸盐和三氟甲磺酸酯都可以平稳反应以得到芳基磺酸盐。形成的芳基磺酸盐可以转化为苯酚，并用作交叉偶联反应的良好伴侣。
• Banana-Shaped Oligo(aryleneethynylene)s: Synthesis and Light-Emitting Characteristics
  作者：Yoshihiro Yamaguchi、Shigeya Kobayashi、Tateaki Wakamiya、Yoshio Matsubara、Zen-ichi Yoshida

  DOI：10.1002/anie.200502214

  日期：2005.11.4
• Rational Design of Potent and Selective Inhibitors of an Epoxide Hydrolase Virulence Factor from <i>Pseudomonas aeruginosa</i>
  作者：Seiya Kitamura、Kelli L. Hvorecny、Jun Niu、Bruce D. Hammock、Dean R. Madden、Christophe Morisseau

  DOI：10.1021/acs.jmedchem.6b00173

  日期：2016.5.26

  The virulence factor cystic fibrosis transmembrane conductance regulator (CFTR) inhibitory factor (Cif) is secreted by Pseudomonas aeruginosa and is the founding member of a distinct class of epoxide hydrolases (EHs) that triggers the catalysis-dependent degradation of the CFTR. We describe here the development of a series of potent and selective Cif inhibitors by structure-based drug design. Initial screening revealed la (KB2115), a thyroid hormone analog, as a lead compound with low micromolar potency. Structural requirements for potency were systematically probed, and interactions between Cif and la were characterized by X-ray crystallography. On the basis of these data, new compounds were designed to yield additional hydrogen bonding with residues of the Cif active site. From this effort, three compounds were identified that are 10-fold more potent toward Cif than our first-generation inhibitors and have no detectable thyroid hormone-like activity. These inhibitors will be useful tools to study the pathological role of Cif and have the potential for clinical application.
• How the π Conjugation Length Affects the Fluorescence Emission Efficiency
  作者：Yoshihiro Yamaguchi、Yoshio Matsubara、Takanori Ochi、Tateaki Wakamiya、Zen-ichi Yoshida

  DOI：10.1021/ja8040493

  日期：2008.10.22

  How the pi conjugation length affects the fluorescence emission efficiency is elucidated by examination of the theoretical and experimental relationship between absolute quantum yield (Phi(f)) and magnitude (Api) of the pi conjugation length in the excited singlet state, which provides a novel concept for molecular design for highly fluorescent organic compounds. As a tool to predict Phi(f) from a structural model, (nu(a) - nu(f))1/2 x a3/2 (nu(a): wavenumber of absorption maximum, nu(f): wavenumber of emission maximum, a: molecular radius) could be used instead of Api. The concept should be valuable for potential applications to (1) examination of an excited singlet state structure (for example, coplanarity of excited-state molecules) and (2) molecular design of novel materials, in which the excited singlet state plays an important role, such as highly efficient fluorophores, electroluminescent materials, photoconducting materials, and nonlinear optical materials. A remarkably intense green fluorophore (Phi(f) 0.88, log epsilon 4.72, lambda(em) 527 nm) is created based on this concept, which is of great interest in relation to a green fluorescent protein (Topaz, T203Y type, Phi(f) 0.60, log epsilon 4.98, lambda(em) 527 nm).