pentafluorophenylboronic acid isopropyl ester | 267006-38-2

• 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: pentafluorophenylboronic acid isopropyl ester
• 英文别名: pentafluoroboronic acidd iisopropyl ester；Dipropan-2-yl (pentafluorophenyl)boronate；(2,3,4,5,6-pentafluorophenyl)-di(propan-2-yloxy)borane
• CAS: 267006-38-2
• 化学式: C₁₂H₁₄BF₅O₂
• 分子量: 296.045
• InChiKey: DEMAYXBBHNHINF-UHFFFAOYSA-N

物化性质

• 沸点：
  260.2±40.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.93
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• 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：
  7

反应信息

• 作为反应物：
  描述：

  pentafluorophenylboronic acid isopropyl ester 在 双氧水 作用下， 以 水 、 均三甲苯 为溶剂， 反应 16.8h， 以95.7%的产率得到五氟苯酚
  参考文献：
  名称：

  フルオロフェノール類の製造方法

  摘要：

  要解决的问题：提供一种生产氟酚化合物的方法，使得可以通过单阶段反应过程合成氟酚化合物。

  解决方案：通过将由通式（1）表示的（氟芳基）硼化合物与过氧化物反应来生产氟酚化合物。在该式中，R1、R2、R3、R4和R5分别独立地是氢原子、氟原子、碳氢基团或烷氧基；R1至R5中至少有一个是氟原子；R6是碳氢基团；n是1-3的整数。

  版权所有：（C）2005，JPO&NCIPI

  公开号：

  JP2005082548A
• 作为产物：
  描述：

  硼酸三异丙酯 、 溴五氟苯 在 异丙基氯化镁 作用下， 以 乙醚 为溶剂， 反应 1.5h， 以80%的产率得到pentafluorophenylboronic acid isopropyl ester
  参考文献：
  名称：

  Requirements for Selective Hydrophobic Acceleration in the Reduction of Ketones

  摘要：

  Reductions of various quaternized hydrophobic beta-keto amines were performed in water and in methanol using borohydride anions carrying hydrophobic groups. The most important requirement of the substrate to permit hydrophobically accelerated selective reductions is the ability of the hydrophobic group of the substrate and its attached keto group to attain a coplanar relationship. Some derivatives of naturally occurring steroid diones have also been employed as substrates to probe the mechanism and utility of these hydrophobically accelerated selective reductions further.

  DOI：

  10.1021/ol0481481

文献信息

• Ligand exchange and abstraction reactions involving titanium isopropoxide with tris(pentafluorophenyl)borane and -alane: ramifications for ring-opening polymerization of propylene oxide
  作者：Antonio Rodriguez-Delgado、Eugene Y.-X. Chen

  DOI：10.1016/j.ica.2004.05.015

  日期：2004.11

  In situ mixing of Ti((OPr)-Pr-i)(4) and B(C6F5)(3) generates a very efficient catalyst system for ring-opening polymerization (ROP) of propylene oxide (PO) with a turnover frequency (TOF) >1350/h, whereas the mixture of Ti((OPr)-Pr-i)(4) and Al(C6F5)(3) is inactive for the same polymerization. The inactivity of the Ti((OPr)-Pr-i)(4)/Al(C6F5)(3) mixture is due to the formation of the stable isopropoxy-bridged bimetallic species Ti((OPr)-Pr-i)(3)(mu-(OPr)-Pr-i)Al(C6F5)(3) (1), the structure of which has been confirmed by X-ray diffraction. The products of the Ti((OPr)-Pr-i)(4) + B(C6F5)(3) reaction, however, depend on the Ti((OPr)-Pr-i)(4):B(C6F5)(3) ratio. The 1: 1 ratio reaction in toluene at ambient temperature is rapid and produces the ligand exchange products: Ti((OPr)-Pr-i)(3)C6F5 and (PrOB)-Pr-i(C6F5)(2) (2), along with a small amount of ((PrO)-Pr-i)(2)BC6F5. The two resulting boranes are inseparable by recrystallization or vacuum distillation, and the formation of the undesired ((PrO)-Pr-i)(2)BC6F5 is either significantly enhanced upon heating the reaction in toluene to 80degreesC or nearly exclusive by carrying out the reaction in THF. By employing 1.2 equiv. of B(C6F5)(3) in the reaction with Ti((OPr)-Pr-i)(4), however, the formation of ((PrO)-Pr-i)(2)BC6F5 is suppressed, enabling the isolation of the new borane 2 in its pure state. The excess of B(C6F5)3 added to the reaction apparently slows down the exchange reaction by stabilizing the intermediate Ti((OPr)-Pr-i)(3)(mu-(OPr)-Pr-i)B(C6F5)(3) (4), as shown by the 1:2 Ti((OPr)-Pr-i)(4):B(C6F5)(3) reaction which initially forms the ligand abstraction product 4 followed by subsequent slow ligand exchange to give the final products Ti((OPr)-Pr-i)(3)C6F5 and 2. The studies of these individual reactions, in combination with control polymerization runs, reveal that the active species responsible for the catalytic activity of the Ti((OPr)-Pr-i)(4)/B(C6F5)(3) mixture is the isopropoxy borane 2. Thus, the isolated 2, in the absence or presence of a hydroxylic initiator, serves as a very effective catalyst for the ROP of PO, producing PPOs with M-n = 2000-3000, M-w/M-n = 1.30-1.43, and TOF > 1400/h. The MALDI-TOF NIS analyses of the PPOs formed show the linear PPO structures having the initiator and water molecules as end groups, demonstrating the control over the PPO structure. (C) 2004 Elsevier B.V. All rights reserved.
• Requirements for Selective Hydrophobic Acceleration in the Reduction of Ketones
  作者：Mark R. Biscoe、Christopher Uyeda、Ronald Breslow

  DOI：10.1021/ol0481481

  日期：2004.11.1

  Reductions of various quaternized hydrophobic beta-keto amines were performed in water and in methanol using borohydride anions carrying hydrophobic groups. The most important requirement of the substrate to permit hydrophobically accelerated selective reductions is the ability of the hydrophobic group of the substrate and its attached keto group to attain a coplanar relationship. Some derivatives of naturally occurring steroid diones have also been employed as substrates to probe the mechanism and utility of these hydrophobically accelerated selective reductions further.
• フルオロフェノール類の製造方法
  申请人：株式会社日本触媒

  公开号：JP2005082548A

  公开（公告）日：2005-03-31

  PROBLEM TO BE SOLVED: To provide a method for producing a fluorophenol compound enabling the synthesis of the fluorophenol compound by a single stage reaction process.

  SOLUTION: A fluorophenol compound is produced by reacting a (fluorinated aryl)boron compound expressed by general formula (1) with a peroxide. In the formula, R1, R2, R3, R4 and R5 are each independently a hydrogen atom, a fluorine atom, a hydrocarbon group or an alkoxy group; at least one of R1 to R5 is a fluorine atom; R6 is a hydrocarbon group; and n is an integer of 1-3.

  COPYRIGHT: (C)2005,JPO&NCIPI

  要解决的问题：提供一种生产氟酚化合物的方法，使得可以通过单阶段反应过程合成氟酚化合物。

  解决方案：通过将由通式（1）表示的（氟芳基）硼化合物与过氧化物反应来生产氟酚化合物。在该式中，R1、R2、R3、R4和R5分别独立地是氢原子、氟原子、碳氢基团或烷氧基；R1至R5中至少有一个是氟原子；R6是碳氢基团；n是1-3的整数。

  版权所有：（C）2005，JPO&NCIPI