4-hydroxyphenyl boroxine | 101763-37-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-hydroxyphenyl boroxine
• 英文别名: 4,4',4''-(1,3,5,2,4,6-trioxatriborinane-2,4,6-triyl)triphenol；2,4,6-tris(4-hydroxyphenyl)boroxin；4-[4,6-Bis(4-hydroxyphenyl)-1,3,5,2,4,6-trioxatriborinan-2-yl]phenol
• CAS: 101763-37-5
• 化学式: C₁₈H₁₅B₃O₆
• 分子量: 359.746
• InChiKey: ISWYRLOXTZDEGW-UHFFFAOYSA-N

物化性质

• 沸点：
  497.8±55.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.35
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  88.4
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-[(叔丁基亚磺酰基)亚氨基]氧杂环丁烷 、 4-hydroxyphenyl boroxine 在 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 1,2-双(二苯基膦基)苯 、 sodium ethanolate 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 以30%的产率得到N-(3-(4-hydroxyphenyl)oxetan-3-yl)-2-methylpropane-2-sulfinamide
  参考文献：
  名称：

  Highly Functional Group Compatible Rh-Catalyzed Addition of Arylboroxines to Activated N-tert-Butanesulfinyl Ketimines

  摘要：

  The rhodium-catalyzed addition of readily accessible arylboroxines to N-tert-butanesulfinyl ketimines derived from oxetan-3-one, N-Boc-azetidin-3-one, and isatins proceeds In high yields with excellent functional group compatibility. Moreover, high diastereoselectivities are observed for the additions to the N-sulfinyl ketimines derived from isatins.

  DOI：

  10.1021/ol201438k
• 作为产物：
  描述：

  4-羟基苯硼酸 生成 4-hydroxyphenyl boroxine
  参考文献：
  名称：

  Oxidative Heck desymmetrisation of 2,2-disubstituted cyclopentene-1,3-diones

  摘要：

  氧化Heck偶联反应已成功用于2,2-二取代环戊烯-1,3-二酮。直接偶联到2,2-二取代环戊烯-1,3-二酮核心提供了一种新颖、迅速和有用的方法，用于非对称化全碳季铵中心。

  DOI：

  10.1039/c5cc00407a

文献信息

• Ligand- and Base-Free Pd(II)-Catalyzed Controlled Switching between Oxidative Heck and Conjugate Addition Reactions
  作者：Sarah E. Walker、Julian Boehnke、Pauline E. Glen、Steven Levey、Lisa Patrick、James A. Jordan-Hore、Ai-Lan Lee

  DOI：10.1021/ol400539h

  日期：2013.4.19

  solvent allows controlled and efficient switching between oxidative Heck and conjugate addition reactions on cyclic Michael acceptor substrates, catalyzed by a cationic Pd(II) catalyst system. Both reactions are ligand- and base-free and tolerant of air and moisture, and the controlled switching sheds light on some of the factors which favor one reaction over the other.

  简单地改变溶剂即可在阳离子Pd（II）催化剂体系的催化下，在环迈克尔受体底物上的氧化Heck反应和共轭加成反应之间进行受控且有效的转换。两种反应均不含配体和碱，并且耐空气和湿气，并且受控的转换揭示了一些有利于一种反应优于另一种的因素。
• Photoinduced Transition-Metal-Free Chan–Evans–Lam-Type Coupling: Dual Photoexcitation Mode with Halide Anion Effect
  作者：Zijun Zhou、Jeonguk Kweon、Hoimin Jung、Dongwook Kim、Sangwon Seo、Sukbok Chang

  DOI：10.1021/jacs.2c03343

  日期：2022.5.25

  large-scale reactions, synthesis of 15N-labeled arylamides, and applicability toward biologically relevant compounds. On the basis of mechanistic investigations, two distinctive photoexcitations are proposed to function in the current process, in which the first excitation involving chloro-boron adduct facilitates the transition-metal-free activation of dioxazolones by single electron transfer (SET), and

  在此，我们报道了作为芳基源的 2,4,6-三（芳基）环硼氧烷或芳基硼酸与 1,4,2-二恶唑-5-酮之间光诱导的无过渡金属的 C（芳基）-N 键形成（二恶唑酮）作为酰胺偶联伙伴。人们发现，氯阴离子无论是通过氯化溶剂分子的光解原位产生还是作为添加剂单独添加，都发挥着关键的协同作用，从而可以在温和的光照条件下方便地获得各种合成多功能的N-芳基酰胺。这种无过渡金属的 Chan-Evans-Lam 型偶联的合成优点通过大规模反应、 15 个N 标记芳酰胺的合成以及对生物相关化合物的适用性得到了证明。在机理研究的基础上，提出了两种独特的光激发在当前过程中发挥作用，其中涉及氯硼加合物的第一种激发通过单电子转移（SET）促进二恶唑酮的无过渡金属活化，第二种激发一种使得由此形成的N-氯酰胺基-硼酸盐加合物能够进行否则无效的1,2-芳基迁移。
• Mild and Ligand-Free Pd(II)-Catalyzed Conjugate Additions to Hindered γ-Substituted Cyclohexenones
  作者：James A. Jordan-Hore、James N. Sanderson、Ai-Lan Lee

  DOI：10.1021/ol300794a

  日期：2012.5.18

  Ligand-free cationic Pd(II) catalyst with NaNO3 as an additive is a highly active catalytic system for conjugate additions to sterically hindered gamma-substituted cyclohexenones. More challenging gamma gamma- and beta gamma-substrates also react well to produce products with quaternary centers in good dr. The conjugate additions occur in a diastereoselective fashion under mild, practical and air-stable conditions, using readily available commercial reagents.
• Rhodium-Catalyzed Domino Conjugate Addition−Cyclization Reactions for the Synthesis of a Variety of <i>N</i>- and <i>O</i>-Heterocycles: Arylboroxines as Effective Carbon Nucleophiles
  作者：Ja Ock Park、So Won Youn

  DOI：10.1021/ol100610v

  日期：2010.5.21

  Facile and efficient Rh(I)-catalyzed domino conjugate addition-cyclization reactions of olefins bearing two electrophilic sites and a pendant nucleophile with organoboroxines have been developed to afford a variety of N- and O-heterocycles, such as 3,4-dihydroquinolin-2(1H)-ones, 3,4-dihydrocoumarins, and pyrrolidin-2-ones, which constitute important motifs in biologically active natural and synthetic organic compounds.