1-fluoro-2-(hexyloxy)benzene | 203115-86-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-fluoro-2-(hexyloxy)benzene
• 英文别名: 1-fluoro-2-hexyloxybenzene；Benzene, 1-fluoro-2-(hexyloxy)-；1-fluoro-2-hexoxybenzene
• CAS: 203115-86-0
• 化学式: C₁₂H₁₇FO
• 分子量: 196.265
• InChiKey: XIXOSIMYFBPPFE-UHFFFAOYSA-N

物化性质

• 沸点：
  255.1±13.0 °C(Predicted)
• 密度：
  0.980±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-fluoro-2-(hexyloxy)benzene 在 正丁基锂 、 氯化亚砜 、 五氯化磷 作用下， 以 四氢呋喃 、 吡啶 、 甲苯 为溶剂， 生成 [4-(4-Hexoxyphenoxy)carbonylphenyl] 2-fluoro-3-hexoxybenzoate
  参考文献：
  名称：

  4-(4-烷氧基苯氧基羰基)苯基3-烷氧基-2-X-苯甲酸酯的合成及热性能

  摘要：

  摘要 4-(4-alkoxyphenoxycarbonyl)phenyl 3-alkoxy-2-X-benzoates (X = F, Cl, Br, or CF3) 的一些衍生物是通过邻位锂化和亲电芳香取代反应合成的，作为关键步骤，并检查了它们的液晶的热性能。这些结果在分子结构和静电效应方面进行了讨论。

  DOI：

  10.1080/15421400590957071
• 作为产物：
  描述：

  6-氯-1-己醇 、 2-氟苯酚 在 resin-bound-Se-B(OEt)3(-)*Na(+) 、 N-甲基吗啉 、 diisopropyl (E)-azodicarboxylate 、 三苯基膦 、 偶氮二异丁腈 、 (Me₃Si)SiH 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 32.0h， 生成 1-fluoro-2-(hexyloxy)benzene
  参考文献：
  名称：

  Green Traceless Cleavage from Resin-Bound Selenium and Tellurium and Analysis by 2D²⁹Si/¹H HR-MAS NMR Spectroscopy

  摘要：

  一种用于从树脂结合的硒和碲中无痕迹切割的新型协议被描述。先前作为通过均裂反应从这些树脂中切割的试剂而使用的毒性较高的三丁基锡氢化物已被替换为毒性较低的三(三甲基硅基)硅烷和三(三甲基硅基)锗烷。此外，通过使用高分辨率魔角旋转(HR-MAS)二维29Si/1H核磁共振光谱法对剩余的树脂结合的亚硒硅烷和锗烷残基进行了表征。

  DOI：

  10.1055/s-2005-865311

文献信息

• Mechanistic study on iodine-catalyzed aromatic bromination of aryl ethers by N -Bromosuccinimide
  作者：Pranab Kumar Pramanick、Zhen-Lin Hou、Bo Yao

  DOI：10.1016/j.tet.2017.10.073

  日期：2017.12

  Although iodine-catalyzed reaction has rapid advances in recent years, examples on iodine-catalyzed bromination are rare and the mechanism of these reactions remains unclear. Herein, we reported an I2-catalyzed aromatic bromination of aryl ethers by NBS and presented the details of the mechanistic study including kinetic study and the study of kinetic isotope effects. The study revealed that the reaction

  尽管近年来碘催化的反应发展迅速，但是碘催化溴化的例子很少，这些反应的机理尚不清楚。在本文中，我们报道了NBS的I 2催化的芳基醚的芳族溴化反应，并详细介绍了包括动力学研究和动力学同位素效应在内的机理研究。研究表明，该反应实际上是由诱导期形成的IBr催化的，而决定速率的步骤是在IBr辅助下消除Wheland中间体的HBr。
• Traceless Solid Phase Synthesis with Polystyrene-Bound Tellurium and in Comparison with Polystyrene-Bound Selenium
  作者：Thomas Ruhland、Jakob Torang、Henrik Pedersen、Jens Christian Madsen、Kia Svane Bang

  DOI：10.1055/s-2004-831202

  日期：——

  A novel traceless linking strategy by use of polystyrene-bound tellurium is described. The application of the tellurium linker is demonstrated by the solid phase synthesis of a small library of single alkyl aryl ethers containing two points of diversity. Polystyrene-bound tellurium and polystyrene-bound selenium are compared by their cleavage performance under radical conditions (homolysis) at different

  描述了一种使用聚苯乙烯结合碲的新型无痕连接策略。碲接头的应用通过固相合成一个包含两个多样性点的单个烷基芳基醚的小型文库来证明。聚苯乙烯结合的碲和聚苯乙烯结合的硒通过它们在不同温度下的自由基条件（均裂）下的裂解性能进行比较。此外，通过使用高分辨率魔角旋转 (HR-MAS) 核磁共振光谱分析了聚苯乙烯结合的基材。
• Solid support based on selenium useful in solid phase synthesis
  申请人：H. Lundbeck A/S

  公开号：US20040171072A1

  公开（公告）日：2004-09-02

  This invention relates to novel solid support based on selenium and a method for the preparation thereof. The solid support is useful in solid phase synthesis of organic compounds including combinatorial libraries of compounds.

  本发明涉及基于硒的新型固体支持物及其制备方法。该固体支持物可用于有机化合物（包括化合物组合库）的固相合成。
• Improvement of Pharmacological Properties of Irreversible Thyroid Receptor Coactivator Binding Inhibitors
  作者：Jong Yeon Hwang、Leggy A. Arnold、Fangyi Zhu、Aaron Kosinski、Thomas J. Mangano、Vincent Setola、Bryan L. Roth、R. Kiplin Guy

  DOI：10.1021/jm9002704

  日期：2009.7.9

  We have previously reported the discover), and preliminary structure activity relationships of a series of beta-aminoketones that disrupt the binding of coactivators to TR. However, the most active compounds had moderate inhibitory potency and relatively high cytotoxicity, resulting in narrow therapeutic index. Additionally, preliminary evaluation of in vivo toxicology revealed a significant dose related cardiotoxicity. Here we describe the improvement of pharmacological properties of thyroid hormone receptor coactivator binding inhibitors. A comprehensive Survey of the effects of substitutents in key areas of the molecule was carried out based on mechanistic insight from the earlier report. This study revealed that both electron withdrawing and hydrophobic substituents on the aromatic ring led to higher potency. On the other hand, moving from an alkyl to a sulfonyl alkyl side chain led to reduced cytotoxicity, Finally, utilization of airline moieties having low pK(a)'s resulted in lowered ion channel activity without any loss of pharmacological activity.
• Selenium-Linking Strategy for Traceless Solid-Phase Synthesis:  Direct Loading, Aliphatic C−H Bond Formation upon Cleavage and Reaction Monitoring by Gradient MAS NMR Spectroscopy
  作者：Thomas Ruhland、Kim Andersen、Henrik Pedersen

  DOI：10.1021/jo9806310

  日期：1998.12.1

  The development of a novel traceless linking strategy for the solid-phase synthesis of small nonpeptide compounds by the use of resin-bound selenium is described. Compounds were attached by direct loading without the requirement of an auxiliary spacer. We demonstrate the synthesis of a small [2 x 3]-sized library of single alkyl aryl ethers with two points of diversity by the Mitsunobu reaction. The selenium-alkyl bond that attaches the alkyl aryl ethers to the resin was smoothly cleaved under radical conditions by homolysis with tributylstannane and catalytic amount of AIBN to generate an aliphatic C-H bond in the liberated ethers. The selenium atom remains immobilized during the entire synthesis, and in the cleavage step, tributylstannyl phenyl selenide is scavenged on the resin. Reaction monitoring was facilitated by the use of gradient high-resolution magic angle spinning 2D-NMR. This new linking method can be applied to solid-phase synthesis of many classes of organic compounds under a broad variation of reaction conditions.