[(E)-2-(1-萘基)乙烯基]硼酸 | 352525-97-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: [(E)-2-(1-萘基)乙烯基]硼酸
• 中文别名: 7-氧杂二环[4.1.0]庚烷-2-羧酸
• 英文名称: (E)-(2-(naphthalen-1-yl)vinyl)boronic acid
• 英文别名: [(E)-2-naphthalen-1-ylethenyl]boronic acid
• CAS: 352525-97-4
• 化学式: C₁₂H₁₁BO₂
• 分子量: 198.029
• InChiKey: KALBJZHUZHGTCI-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.87
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2931900090

反应信息

• 作为反应物：
  描述：

  [(E)-2-(1-萘基)乙烯基]硼酸 以 甲苯 为溶剂， 反应 3.0h， 生成 2,4,6-tris((E)-2-(naphthalen-1-yl)vinyl)boroxine
  参考文献：
  名称：

  Arylation and Vinylation of α-Diazocarbonyl Compounds with Boroxines

  摘要：

  An alternative approach for alpha-arylation and alpha-vinylation of carbonyl compounds is described: reaction between aryl- or vinylboroxines with alpha-diazocarbonyl compounds leads to the formation of alpha-arylated or alpha-vinylated carbonyl compounds under mild conditions.

  DOI：

  10.1021/ol900362d
• 作为产物：
  描述：

  1-乙基萘 在 儿萘酚硼烷 作用下， 反应 1.0h， 以61%的产率得到[(E)-2-(1-萘基)乙烯基]硼酸
  参考文献：
  名称：

  Synthesis and evaluation of 4-(substituted styryl/alkenyl)-3,5-bis(4-hydroxyphenyl)-isoxazoles as ligands for the estrogen receptor

  摘要：

  A series of 3,5-bis(4-hydroxyphenyl) isoxazoles bearing a styryl/alkyl vinyl group at the 4-position were prepared and evaluated as ligands for the estrogen receptor-alpha (ER alpha). The target compounds were prepared using the Suzuki reaction to couple an iodo-isoxazole intermediate with a series of styryl/alkenyl boronic acids, followed by O-demethylation. The products were evaluated for their estrogen receptor-alpha ligand binding domain (ER alpha-LBD) binding affinity using a competitive binding assay. The 4-(4-hydroxy-styryl) derivative 4 h displays binding properties similar to those of the previously described pyrazole class of ER ligands, indicating that the ER alpha-LBD tolerates the presence of the added vinyl group at the 4-position of the isoxazole ring. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.097

文献信息

• Copper-Catalyzed Oxyvinylation of Diazo Compounds
  作者：Guillaume Pisella、Alec Gagnebin、Jerome Waser

  DOI：10.1021/acs.orglett.0c01150

  日期：2020.5.15

  copper(I)-catalyzed vinylation of diazo compounds with vinylbenziodoxolone reagents (VBX) as partners is reported. The transformation tolerates diverse functionalities on both reagents delivering polyfunctionalized vinylated products. The strategy was successfully extended to a three-component/intermolecular version with alcohols. The obtained products contain synthetically versatile functional groups, such

  报道了铜（I）与乙烯基苯并恶唑酮试剂（VBX）一起对重氮化合物进行乙烯基化。该转化在两种试剂中均具有多种功能，可提供多官能化的乙烯基化产物。该策略已成功扩展到含酒精的三组分/分子间形式。所得产物包含合成上通用的官能团，例如芳基碘化物，酯和烯丙基离去基团，从而能够进行进一步修饰。
• Organophotocatalytic Radical–Polar Cross-Coupling of Styrylboronic Acids and Redox-Active Esters
  作者：Allan J. B. Watson、Jeremy Brals、Nicholas D’Arcy-Evans、Thomas M. McGuire

  DOI：10.1055/a-2179-6570

  日期：2024.1

  We report the development of a radical–polar cross-coupling reaction using styrylboronic acids and redox-active esters under organophotoredox catalysis. The reaction proceeds through a formal polarity-mismatched radical addition. The use of an organic photocatalyst permitted very low loadings of the electron-shuttle additive and accelerated reaction times compared with established processes. The scope

  我们报告了在有机光氧化还原催化下使用苯乙烯基硼酸和氧化还原活性酯进行自由基-极性交叉偶联反应的进展。该反应通过正式的极性不匹配的自由基加成进行。与现有工艺相比，有机光催化剂的使用使得电子穿梭添加剂的用量非常低，并加快了反应时间。探索了反应的范围，并证明了产品的实用性。
• A Chemoselective Polarity‐Mismatched Photocatalytic C(sp³)−C(sp²) Cross‐Coupling Enabled by Synergistic Boron Activation**
  作者：Jeremy Brals、Thomas M. McGuire、Allan J. B. Watson

  DOI：10.1002/anie.202310462

  日期：2023.10.16

  We report a rare polarity-mismatched radical addition reaction using styrene boronic acids and redox-active N-hydroxyphthalimide (NHPI) esters under photoredox catalysis. The reaction displays broad scope with mechanistic investigations supporting a unique synergistic activation pathway that displays chemoselectivity for styrene boronic acids in the presence of other SOMOphiles. SOMO=singly occupied

  我们报道了在光氧化还原催化下使用苯乙烯硼酸和氧化还原活性N-羟基邻苯二甲酰亚胺 (NHPI) 酯进行罕见的极性不匹配自由基加成反应。该反应显示出广泛的范围，机制研究支持独特的协同激活途径，该途径在其他亲SOMO试剂存在的情况下显示出苯乙烯硼酸的化学选择性。 SOMO=单占据分子轨道。
• Manganese(I)‐Catalyzed Enantioselective C(sp²)−C(sp³) Bond‐Forming for the Synthesis of Skipped Dienes with Synergistic Aminocatalysis
  作者：Chuan‐Gang Zhao、Junzhe Cai、Chaoyu Du、Qi Gao、Jie Han、Jin Xie

  DOI：10.1002/anie.202400177

  日期：2024.5.6

  synergistic catalytic strategy has addressed the great challenge in Mn(I)-catalyzed enantioselective C−C bond coupling. A variety of structurally diverse skipped 1,4-dienes are furnished in synthetically useful yields and good enantioselectivity. This strategy has also been applied for the total synthesis of the analogues of (−)-Blepharocalyxin D.

  协同催化策略解决了 Mn(I) 催化的对映选择性 C−C 键偶联的巨大挑战。提供了多种结构多样的跳过 1,4-二烯，具有合成上有用的产率和良好的对映选择性。该策略也已应用于 (−)-Blepharocalyxin D 类似物的全合成。
• Carbene-Catalyzed Enantioselective Petasis-Like Alkenylation
  作者：Zhipeng Li、Jingyang Zhang、Yani Li、Jiahui Zhou、Shujie Ji、Gongming Yang、Yefeng Tang、Jian Wang

  DOI：10.1021/acscatal.3c05289

  日期：2024.2.2