2-氯-6-氟苯硼酸频呢醇酯 | 1599432-38-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-氯-6-氟苯硼酸频呢醇酯
• 英文名称: 2-(2-chloro-6-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• 英文别名: 2-(2-Chloro-6-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS: 1599432-38-8
• 化学式: C₁₂H₁₅BClFO₂
• 分子量: 256.512
• InChiKey: VKTLHYCBHWLRAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.78
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-氯-6-氟苯硼酸频呢醇酯 、 在 XPhos Pd G2 、 sodium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 以38%的产率得到(R)-4-(2-chloro-6-fluorophenyl)-2-(2,6-difluorophenyl)-1-(2-hydroxypropyl)-5-methyl-1H-pyrazol-3(2H)-one
  参考文献：
  名称：

  19F NMR spectroscopy as a tool to detect rotations in fluorine substituted phenyl compounds

  摘要：

  Atropisomerism becomes a popular structural feature in modern drug discovery. Using N-phenyl gamma-lactam and phenyl-pyrazolone scaffolds, we showed that distinct F-19 NMR peaks were present in atropisomers and dual signals emerged for covalently identical fluorine nuclei in hindered rotamers. Factors affecting F-19 NMR chemical shifts in these molecules were discussed. We demonstrated that F-19 NMR spectroscopy can be used to differentiate and detect atropisomers and rotamers in conformationally restricted molecules. (C) 2020 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2020.131679
• 作为产物：
  描述：

  2-(4-Bromo-2-chloro-6-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 在 potassium fluoride 、 palladium diacetate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 28.0h， 以85%的产率得到2-氯-6-氟苯硼酸频呢醇酯
  参考文献：
  名称：

  A Catalytic Borylation/Dehalogenation Route to o-Fluoro Arylboronates

  摘要：

  A two-step Ir-catalyzed borylation/Pd-catalyzed dehalogenation sequence allows for the net synthesis of fluoroarenes where the boronic ester is ortho to fluorine. Key elements of this approach include the use of a halogen para to the fluorine to block meta Ir-catalyzed borylation and the chemoselective Pd-catalyzed dehalogenation by KF activated polymethylhydrosiloxane (PMHS).

  DOI：

  10.1021/ol5028738

文献信息

• Transition Metal-Free Synthesis of Pinacol Arylboronate: Regioselective Boronation of 1,3-Disubstituted Benzenes
  作者：Yan Wang、Le Wang、Ling-Yan Chen、Pinaki S. Bhadury、Zhihua Sun

  DOI：10.1071/ch13642

  日期：——

  The regioselective synthesis of pinacol arylboronate has been achieved from 1,3-disubstituted benzene through directed ortho-metallation (DoM)–borylation sequence. A wide range of substituents and borylating reagents were investigated. In situ lithiation and subsequent boronation predominantly occurred at the ortho-position to afford the desired products in moderate yields.

  通过定向正交金属化（DoM）-硼酸化顺序，从 1,3 二甲基苯实现了芳基硼酸频哪醇酯的区域选择性合成。研究了多种取代基和硼酸化试剂。原位锂化和随后的硼化主要发生在正交位置，从而以中等产率得到所需的产物。
• [EN] ISOQUINOLINE DERIVATIVES AS SIK2 INHIBITORS<br/>[FR] DÉRIVÉS D'ISOQUINOLÉINE EN TANT QU'INHIBITEURS DE SIK2
  申请人：CANCER RESEARCH TECH LTD

  公开号：WO2021084264A1

  公开（公告）日：2021-05-06

  Provided are compounds of the Formula I, and salts and solvates thereof: (I) wherein R1, R2, R3, X1, X2, X3 and Z are defined in the specification. The compounds are inhibitors of salt-inducible kinase (SIK), particular SIK2, and are useful in therapy, particularly in the treatment of a proliferative disorder, a benign neoplasm, pathological angiogenesis, an inflammatory disease or condition, a musculoskeletal disease or condition, an autoimmune disease, a haematological disease or condition, a neurological disease or condition, a psychiatric disorder, or a metabolic disorder.

  提供了化合物的公式I，以及其盐和溶剂合物：(I)其中R1、R2、R3、X1、X2、X3和Z在规范中有定义。这些化合物是盐诱导激酶（SIK），特别是SIK2的抑制剂，并且在治疗中非常有用，特别是在治疗增生性疾病、良性肿瘤、病理性血管生成、炎症性疾病或情况、肌肉骨骼疾病或情况、自身免疫疾病、血液疾病或情况、神经疾病或情况、精神障碍或代谢性疾病的治疗中。
• A Catalytic Borylation/Dehalogenation Route to <i>o</i>-Fluoro Arylboronates
  作者：Chathurika R. K. Jayasundara、Jason M. Unold、Jossian Oppenheimer、Milton R. Smith、Robert E. Maleczka

  DOI：10.1021/ol5028738

  日期：2014.12.5

  A two-step Ir-catalyzed borylation/Pd-catalyzed dehalogenation sequence allows for the net synthesis of fluoroarenes where the boronic ester is ortho to fluorine. Key elements of this approach include the use of a halogen para to the fluorine to block meta Ir-catalyzed borylation and the chemoselective Pd-catalyzed dehalogenation by KF activated polymethylhydrosiloxane (PMHS).
• 19F NMR spectroscopy as a tool to detect rotations in fluorine substituted phenyl compounds
  作者：Mingming Sun、Wuhong Chen、Tao Zhang、Zhenjun Liu、Junchao Wei、Ning Xi

  DOI：10.1016/j.tet.2020.131679

  日期：2020.11

  Atropisomerism becomes a popular structural feature in modern drug discovery. Using N-phenyl gamma-lactam and phenyl-pyrazolone scaffolds, we showed that distinct F-19 NMR peaks were present in atropisomers and dual signals emerged for covalently identical fluorine nuclei in hindered rotamers. Factors affecting F-19 NMR chemical shifts in these molecules were discussed. We demonstrated that F-19 NMR spectroscopy can be used to differentiate and detect atropisomers and rotamers in conformationally restricted molecules. (C) 2020 Elsevier Ltd. All rights reserved.