3,5-bis(pentafluorosulfanyl)phenylboronic acid | 871507-71-0

• 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: 3,5-bis(pentafluorosulfanyl)phenylboronic acid
• 英文别名: (3,5-Bis(pentafluoro-l6-sulfaneyl)phenyl)boronic acid；[3,5-bis(pentafluoro-λ6-sulfanyl)phenyl]boronic acid
• CAS: 871507-71-0
• 化学式: C₆H₅BF₁₀O₂S₂
• 分子量: 374.032
• InChiKey: FSXQEWCCKFEJDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.68
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  42.5
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  3,5-bis(pentafluorosulfanyl)phenylboronic acid 、 4-碘酞腈 在 potassium phosphate 、 palladium diacetate 、 三苯基膦 作用下， 以 水 、 甲苯 为溶剂， 以62%的产率得到3',5'-bis-pentafluorosulfanyl-biphenyl-3,4-dicarbonitrile
  参考文献：
  名称：

  Synthesis and property of novel phthalocyanine having a 3,5-bis-pentafluorosulfanylphenyl group on the α-peripheral position

  摘要：

  The pentafluorosulfanyl (SF5) group is bulky, highly lipophilic, highly electronegative, and highly stable. Despite the potential use of SF5-containing phthalocyanines, no example exists. We herein report the synthesis of 3,5-bis-pentafluorosulfanylphenyl ((SF5)(2)Ph)-Substituted phthalocyanine onto the alpha-peripheral position for the first time. Regioselective synthesis was possible by the effect of the SF5 moiety via macrocyclization. The synthesis of phthalocyanines with CF3 and H instead of SF5 was also carried out in order to investigate the effect of SF5. Phthalocyanines were compared using UV/Vis spectra. Phthalocyanine with SF5 exists free from aggregation and protonation in dichloromethane solution. The two planes of 3,5-(SF5)(2)Ph and parent Pc ring in space are nearly perpendicular at which they meet is a right angle, while the two planes of CF3 analogue in space are not. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2014.09.012
• 作为产物：
  描述：

  1,3-二(五氟硫基)-5-溴苯 在 异丙基溴化镁 、 硼酸三甲酯 作用下， 以 四氢呋喃 为溶剂， 以73%的产率得到3,5-bis(pentafluorosulfanyl)phenylboronic acid
  参考文献：
  名称：

  Synthesis and property of novel phthalocyanine having a 3,5-bis-pentafluorosulfanylphenyl group on the α-peripheral position

  摘要：

  The pentafluorosulfanyl (SF5) group is bulky, highly lipophilic, highly electronegative, and highly stable. Despite the potential use of SF5-containing phthalocyanines, no example exists. We herein report the synthesis of 3,5-bis-pentafluorosulfanylphenyl ((SF5)(2)Ph)-Substituted phthalocyanine onto the alpha-peripheral position for the first time. Regioselective synthesis was possible by the effect of the SF5 moiety via macrocyclization. The synthesis of phthalocyanines with CF3 and H instead of SF5 was also carried out in order to investigate the effect of SF5. Phthalocyanines were compared using UV/Vis spectra. Phthalocyanine with SF5 exists free from aggregation and protonation in dichloromethane solution. The two planes of 3,5-(SF5)(2)Ph and parent Pc ring in space are nearly perpendicular at which they meet is a right angle, while the two planes of CF3 analogue in space are not. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2014.09.012
• 作为试剂：
  描述：

  Methyl 2-(4-methylbenzoyl)hept-6-ynoate 在 3,5-bis(pentafluorosulfanyl)phenylboronic acid 作用下， 以 甲苯 为溶剂， 反应 58.0h， 以71%的产率得到1-(4-methylbenzoyl)-2-methylenecyclopentanecarboxylic acid methyl ester
  参考文献：
  名称：

  3,5-Bis(pentafluorosulfanyl)phenylboronic acid: A new organocatalyst for Conia-ene carbocyclization of 1,3-dicarbonyl compounds having terminal alkynes

  摘要：

  3,5-Bis(pentafluorosulfanyl)phenylboronic acid 1 was introduced as an efficient organocatalyst for Conia-ene carbocyclization of 1,3-dicarbonyl compounds having terminal alkynes. A variety of 2-alkynic 1,3-dicarbonyl compounds were smoothly converted to ene-carbocyclization products in moderate to excellent yields. Compared with the reported catalyst, 3-nitro phenylboronic acid, catalyst 1 is slightly better in a non-polar solvent such as toluene and Solkane(R) 365mfc (1,1,1,3,3-pentafluorobutane). These results indicate that the SF5 function can be a lipophilic and sterically demanding alternative to the NO2 group in catalyst design. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2012.06.007

文献信息

• Catalytic Asymmetric Torgov Cyclization: A Concise Total Synthesis of (+)-Estrone
  作者：Sébastien Prévost、Nathalie Dupré、Markus Leutzsch、Qinggang Wang、Vijay Wakchaure、Benjamin List

  DOI：10.1002/anie.201404909

  日期：2014.8.11

  dinitro‐substituted disulfonimide, is described. The reaction delivers the Torgov diene and various analogues with excellent yields and enantioselectivity. This method was applied in a very short synthesis of (+)‐estrone.

  描述了一种新型的高度布朗斯台德酸性二硝基取代的二磺酰亚胺催化的不对称Torgov环化反应。该反应以优异的产率和对映选择性提供了Torgov二烯和各种类似物。该方法用于（+）-雌酮的非常短的合成中。
• Pentafluorosulfanyl (SF5) in dyes: C3-Regioselective synthesis of α-mono-substituted subphthalocyanine with SF5-phenyl group
  作者：Norihito Iida、Etsuko Tokunaga、Norimichi Saito、Norio Shibata

  DOI：10.1016/j.jfluchem.2014.08.016

  日期：2015.3

  Pentafluorosulfanyl (SF5) is a unique fluorinated functional group. It has high lipophilicity and electronegativity, and is chemically and thermally stable. In addition, the steric hindrance of SF5 is larger than that of the trifluoromethyl (CF3) group. Therefore the introduction of SF5 group into functional dyes such as phthalocyanines and subphthalocyanines should be an attractive strategy to improve their robustness and alter their optical property. We attempted the C-3-regioselective cyclotrimerization of aryl-substituted phthalonitriles 3 to provide subphthalocyanines (SubPcs) 1. alpha-Mono-substituted SubPc la was C-3-regioselectively synthesized by introducing a bis(SF5)Ph group on the alpha-peripheral position providing 1a as a single isomer. The effect of the SF5 group on the synthesis and optical property of SubPcs were investigated by comparing with the H and CF3 analogues, 1b and 1c. (C) 2014 Elsevier B.V. All rights reserved.