4-(2-chloro-ethoxy)-phenylboronic acid | 252044-23-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(2-chloro-ethoxy)-phenylboronic acid
• 英文别名: 4-(2-Chloroethoxy)phenylboronic acid；[4-(2-chloroethoxy)phenyl]boronic acid
• CAS: 252044-23-8
• 化学式: C₈H₁₀BClO₃
• 分子量: 200.43
• InChiKey: DTEXGVSTBQBCDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.02
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(2-chloro-ethoxy)-phenylboronic acid 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 甲苯 为溶剂， 反应 19.0h， 生成 4'-(2-Ph2PCH2CH2O)-4-(2-Ph2PCH2CH2S)biphenyl
  参考文献：
  名称：

  Halide-Induced Supramolecular Ligand Rearrangement

  摘要：

  A novel reaction involving the halide-induced rearrangement of ligands within supramolecular Rh(I) complexes containing hemilabile ligands is presented. Three analogous bis- and trishemilabile ligands have been synthesized to construct bi- and trimetallic Rh(I) macrocyclic complexes. An intentionally added halide source results in the formal rotation of only one hemilabile ligand along the axis that is perpendicular to the plane defined by the aryl backbone of the hemilabile ligands. X-ray structures, as determined by X-ray crystallography, of key intermediates and products are presented.

  DOI：

  10.1021/ja045316b
• 作为产物：
  描述：

  4-溴苯基 2-氯乙基醚 在 正丁基锂 、 硼酸三甲酯 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 0.5h， 生成 4-(2-chloro-ethoxy)-phenylboronic acid
  参考文献：
  名称：

  Halide-Induced Supramolecular Ligand Rearrangement

  摘要：

  A novel reaction involving the halide-induced rearrangement of ligands within supramolecular Rh(I) complexes containing hemilabile ligands is presented. Three analogous bis- and trishemilabile ligands have been synthesized to construct bi- and trimetallic Rh(I) macrocyclic complexes. An intentionally added halide source results in the formal rotation of only one hemilabile ligand along the axis that is perpendicular to the plane defined by the aryl backbone of the hemilabile ligands. X-ray structures, as determined by X-ray crystallography, of key intermediates and products are presented.

  DOI：

  10.1021/ja045316b

文献信息

• Aluminum Chloride Promoted Cross-Coupling of Trisubstituted Enol Phosphates with Organozinc Reagents En Route to the Stereoselective Synthesis of Tamoxifen and Its Analogues
  作者：Vladislav Kotek、Peter Polák、Hana Dvořáková、Tomáš Tobrman

  DOI：10.1002/ejoc.201600959

  日期：2016.10

  and the reaction conditions tolerate various functional groups. The observed reactivity pattern of trisubstituted enol phosphates was used for the stereoselective preparation of tamoxifen and its analogues.

  描述了一种用于芳基氯化锌与三取代的烯醇磷酸酯的立体选择性交叉偶联反应的新方法。所开发的方法需要氯化铝作为促进剂，反应条件允许各种官能团。观察到的三取代烯醇磷酸酯的反应模式用于立体选择性制备他莫昔芬及其类似物。
• Tuning the Photophysical Properties of Flavins by Attaching an Aryl Moiety via Direct C–C Bond Coupling
  作者：Marek Čubiňák、Naisargi Varma、Petr Oeser、Adam Pokluda、Tetiana Pavlovska、Radek Cibulka、Marek Sikorski、Tomáš Tobrman

  DOI：10.1021/acs.joc.2c02168

  日期：2023.1.6

  Palladium-catalyzed Suzuki reactions of brominated flavin derivatives (5-deazaflavins, alloxazines, and isoalloxazines) with boronic acids or boronic acid esters that occur readily under mild conditions were shown to be an effective tool for the synthesis of a broad range of 7/8-arylflavins. In general, the introduction of an aryl/heteroaryl group by means of a direct C–C bond has been shown to be

  溴化黄素衍生物（5-脱氮黄素、咯嗪和异咯嗪）与硼酸或硼酸酯的钯催化铃木反应在温和条件下很容易发生，被证明是合成范围广泛的 7/8 的有效工具-芳基黄素。一般来说，通过直接 C-C 键引入芳基/杂芳基已被证明是调节黄素衍生物光物理性质的一种有前途的方法。芳基取代基引起高达 52 nm 的吸收光谱的红移，并将荧光寿命延长了高达 1 个数量级。此外，黄素衍生物的芳基化降低了它们产生单线态氧的能力。