(E)-2-(2-fluorophenyl)vinylboronic acid | 877868-68-3

• 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: (E)-2-(2-fluorophenyl)vinylboronic acid
• 英文别名: (E)-(2-Fluorostyryl)boronic acid；[(E)-2-(2-fluorophenyl)ethenyl]boronic acid
• CAS: 877868-68-3
• 化学式: C₈H₈BFO₂
• 分子量: 165.96
• InChiKey: XUDLSHDFOQZUEO-AATRIKPKSA-N

物化性质

• 沸点：
  313.9±44.0 °C(Predicted)
• 密度：
  1.228±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.85
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• 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：
  3

反应信息

• 作为反应物：
  描述：

  (E)-2-(2-fluorophenyl)vinylboronic acid 在 四(三苯基膦)钯 、 potassium tert-butylate 、 sodium carbonate 作用下， 以 乙二醇二甲醚 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 5.5h， 生成 6-[(E)-2-(2-fluorophenyl)ethenyl]-3,4-bis(phenylmethoxy)pyridazine
  参考文献：
  名称：

  4-Hydroxypyridazin-3(2H)-one Derivatives as Novel d-Amino Acid Oxidase Inhibitors

  摘要：

  D-Amino acid oxidase (DAAO) catalyzes the oxidation of D-amino acids including D-serine, a coagonist of the N-methyl-D-aspartate receptor. We identified a series of 4-hydroxypyridazin-3(2H)-one derivatives as novel DAAO inhibitors with high potency and substantial cell permeability using fragment-based drug design. Comparisons of complex structures deposited in the Protein Data Bank as well as those determined with in-house fragment hits revealed that a hydrophobic subpocket was formed perpendicular to the flavin ring by flipping Tyr224 in a ligand-dependent manner. We investigated the ability of the initial fragment hit, 3-hydroxy-pyridine-2(1H)-one, to fill this subpocket with the aid of complex structure information. 3-ydroxy-5-(2-phenylethyl)pyridine-2(1H)-one exhibited the predicted binding mode and demonstrated high inhibitory activity for human DAAO in enzyme- and cell-based assays. We further designed and synthesized 4-hydroxypyridazin-3(2H)-one derivatives, which are equivalent to the 3-hydroxy-pyridine-2(1H)-one series but lack cell toxicity. 6-[2-(3,5-Difluorophenyl)ethyl]-4-hydroxypyridazin-3(2H)-one was found to be effective against MK-801-induced cognitive deficit in the Y-maze.

  DOI：

  10.1021/jm400095b
• 作为产物：
  描述：

  1-乙炔基-2-氟苯 在 儿萘酚硼烷 作用下， 反应 1.0h， 以43%的产率得到(E)-2-(2-fluorophenyl)vinylboronic acid
  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

• <i>N</i>-Heterocyclic Carbene-Catalyzed Olefination of Aldehydes with Vinyliodonium Salts To Generate α,β-Unsaturated Ketones
  作者：Adam A. Rajkiewicz、Marcin Kalek

  DOI：10.1021/acs.orglett.8b00447

  日期：2018.4.6

  of aldehydes with vinyliodonium salts has been achieved by an N-heterocyclic carbene-promoted C–H bond activation. The reaction proceeds under very mild conditions, delivering a range of (hetero)aryl-vinyl ketones in good yields. The retention of the double bond configuration is uniformly observed, and the application of 2-methoxyphenyl auxiliary group in iodonium salts secures a complete selectivity

  通过N-杂环卡宾促进的C-H键活化，可以实现醛类与乙烯基碘鎓盐的无有机催化金属的直接醛化。该反应在非常温和的条件下进行，以良好的产率提供了一系列（杂）芳基-乙烯基酮。均匀地观察到双键构型的保留，并且在碘鎓盐中应用2-甲氧基苯基辅助基团确保了乙烯基转移的完全选择性。
• Photoredox-Catalyzed Intermolecular Remote C–H and C–C Vinylation via Iminyl Radicals
  作者：Xu Shen、Jia-Jia Zhao、Shouyun Yu

  DOI：10.1021/acs.orglett.8b02540

  日期：2018.9.7

  C(sp3)–H and C–C vinylation of O-acyl oximes with vinyl boronic acids has been achieved. This strategy is enabled by photoreductive generation of iminyl radicals from O-acyl oximes under irradiation by visible light. The translocated carbon-centered radicals, which are generated from the iminyl radicals through 1,5-hydrogen atom transfer or C–C cleavage, can be vinylated with vinyl boronic acids. This

  已经实现了用乙烯基硼酸对O-酰基肟进行分子间远程C（sp 3）–H和C–C乙烯基化的统一策略。该策略通过在可见光照射下从O-酰基肟光还原生成亚胺基而实现。亚胺基自由基通过1，5-氢原子转移或CC裂解产生的碳中心自由基可以用乙烯基硼酸乙烯基化。该策略为通过C（sp 3）–H和C–C裂解进行远程官能化开辟了新途径，并为合成酮和腈的γ-乙烯基化提供了一种高效且通用的解决方案。
• 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。
• Synthesis and evaluation of 4-(substituted styryl/alkenyl)-3,5-bis(4-hydroxyphenyl)-isoxazoles as ligands for the estrogen receptor
  作者：Terra Haddad、Rachel Gershman、Robert Dilis、David Labaree、Richard B. Hochberg、Robert N. Hanson

  DOI：10.1016/j.bmcl.2012.06.097

  日期：2012.9

  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.
• 4-Hydroxypyridazin-3(2<i>H</i>)-one Derivatives as Novel <scp>d</scp>-Amino Acid Oxidase Inhibitors
  作者：Takeshi Hondo、Masaichi Warizaya、Tatsuya Niimi、Ichiji Namatame、Tomohiko Yamaguchi、Keita Nakanishi、Toshihiro Hamajima、Katsuya Harada、Hitoshi Sakashita、Yuzo Matsumoto、Masaya Orita、Makoto Takeuchi

  DOI：10.1021/jm400095b

  日期：2013.5.9

  D-Amino acid oxidase (DAAO) catalyzes the oxidation of D-amino acids including D-serine, a coagonist of the N-methyl-D-aspartate receptor. We identified a series of 4-hydroxypyridazin-3(2H)-one derivatives as novel DAAO inhibitors with high potency and substantial cell permeability using fragment-based drug design. Comparisons of complex structures deposited in the Protein Data Bank as well as those determined with in-house fragment hits revealed that a hydrophobic subpocket was formed perpendicular to the flavin ring by flipping Tyr224 in a ligand-dependent manner. We investigated the ability of the initial fragment hit, 3-hydroxy-pyridine-2(1H)-one, to fill this subpocket with the aid of complex structure information. 3-ydroxy-5-(2-phenylethyl)pyridine-2(1H)-one exhibited the predicted binding mode and demonstrated high inhibitory activity for human DAAO in enzyme- and cell-based assays. We further designed and synthesized 4-hydroxypyridazin-3(2H)-one derivatives, which are equivalent to the 3-hydroxy-pyridine-2(1H)-one series but lack cell toxicity. 6-[2-(3,5-Difluorophenyl)ethyl]-4-hydroxypyridazin-3(2H)-one was found to be effective against MK-801-induced cognitive deficit in the Y-maze.