bis[(3,5-bis(trifluoromethyl)phenyl)]borinic acid | 211636-23-6

• 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: bis[(3,5-bis(trifluoromethyl)phenyl)]borinic acid
• 英文别名: bis(3,5-bis(trifluoromethyl)phenyl)borinic acid；bis[3,5-bis(trifluoromethyl)phenyl]borinic acid；B{3,5-(CF₃)₂C₆H₃}₂(OH)
• CAS: 211636-23-6
• 化学式: C₁₆H₇BF₁₂O
• 分子量: 454.023
• InChiKey: ACBUTNALWRXXQK-UHFFFAOYSA-N

物化性质

• 沸点：
  322.1±52.0 °C(Predicted)
• 密度：
  1.53±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.86
• 重原子数：
  30
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  bis[(3,5-bis(trifluoromethyl)phenyl)]borinic acid 、 3-(4'-Hydroxy-[1,1';3',1'']terphenyl-5'-yl)-[1,1']binaphthalenyl-2,2'-diol 在 molecular sieves (MS 4A) 作用下， 以 二氯甲烷 为溶剂， 生成 1-[2-Bis[3,5-bis(trifluoromethyl)phenyl]boranyloxynaphthalen-1-yl]-3-(2-hydroxy-3,5-diphenylphenyl)naphthalen-2-ol
  参考文献：
  名称：

  用于高对映选择性 Diels-Alder 反应的 Brønsted 酸辅助手性路易斯酸 (BLA) 催化剂的设计

  摘要：

  布朗斯台德酸辅助的手性路易斯酸 (BLA) 作为手性催化剂非常有效，可用于 α-取代和 α-未取代的 α,β-烯醛与各种二烯的对映选择性 Diels-Alder 反应。光学活性联萘酚衍生物中的羟基和具有吸电子取代基的硼试剂分别用作布朗斯台德酸和路易斯酸。手性 BLA 催化剂中的分子内布朗斯台德酸在加速 Diels-Alder 反应速率和产生高水平的对映选择性方面发挥了重要作用。特别是，由于手性 BLA 催化剂中羟基芳基在过渡态组装中的分子内氢键相互作用和有吸引力的 π-π 供体-受体相互作用，实现了优异的对映选择性。

  DOI：

  10.1021/ja9810282
• 作为产物：
  描述：

  水 、 四(3,5-二(三氟甲基)苯基)硼酸钠 在 chlorotrioxorhenium 作用下， 生成 bis[(3,5-bis(trifluoromethyl)phenyl)]borinic acid
  参考文献：
  名称：

  Homogeneous Model Complexes for Supported Rhenia Metathesis Catalysts

  摘要：

  A series of rhenium trioxo complexes (L-ReO3) was synthesized, characterized, and demonstrated to be active in olefin metathesis. The relationship between perrhenate (ReO4-), perrhenyl (ReO3+), and metathesis-active rhenium complexes (L-ReO3) was elucidated. Their chemical behavior can be tuned through the Lewis acid-base interaction. DFT calculations were performed for the metathesis reaction of L-ReO3 with norbornene, which demonstrates that electron-withdrawing substituents or ligands are beneficial for olefin metathesis activity. Moreover, a rhenium-alkylidene complex was synthesized, which can be activated by B(C6F5)(3) to afford an active metathesis catalyst. This be regarded as a homogeneous model of the hypothetical species present in the heterogeneous catalytic systems. The findings from the present study are consistent with our previous gas-phase studies and constitute the elucidation of the working principles for the metathesis-active rhenium species on the surface.

  DOI：

  10.1021/om300852s
• 作为试剂：
  描述：

  4-phenyl-2-(trimethylsiloxy)-1-butene 、 苯甲醛 在 盐酸 、 bis[(3,5-bis(trifluoromethyl)phenyl)]borinic acid 作用下， 生成 (E)-1,5-diphenyl-1-penten-3-one 、 1-羟基-1,5-二苯基-戊烷-3-酮
  参考文献：
  名称：

  Diarylborinic Acids as Efficient Catalysts for Selective Dehydration of Aldols

  摘要：

  芳基上带有吸电子取代基的二芳基硼酸是高效的路易斯酸催化剂，用于 Mukaiyama 羟醛缩合以及在顺式羟醛存在下选择性脱水为 α,β-烯酮。二芳基硼酸的路易斯酸度远高于相应的芳基硼酸。

  DOI：

  10.1055/s-1997-3207

文献信息

• Novel B(Ar′)₂(Ar′′) hetero-tri(aryl)boranes: a systematic study of Lewis acidity
  作者：Robin J. Blagg、Trevor R. Simmons、Georgina R. Hatton、James M. Courtney、Elliot L. Bennett、Elliot J. Lawrence、Gregory G. Wildgoose

  DOI：10.1039/c5dt03854e

  日期：——

  Nine homo- and hetero-tri(aryl)boranes related by stepwise aryl substitutions, are studied for H₂ cleavage as part of an FLP, and comparative Lewis acidity/electrochemical measurements discussed.

  研究了通过逐步芳基取代相关的九种同系和异系三(芳基)硼烷，作为FLP的一部分进行H₂裂解，并讨论了比较Lewis酸度/电化学测量。
• Design of Brønsted Acid-Assisted Chiral Lewis Acid (BLA) Catalysts for Highly Enantioselective Diels−Alder Reactions
  作者：Kazuaki Ishihara、Hideki Kurihara、Masayuki Matsumoto、Hisashi Yamamoto

  DOI：10.1021/ja9810282

  日期：1998.7.1

  Bronsted acid-assisted chiral Lewis acid (BLA) was highly effective as a chiral catalyst for the enantioselective Diels−Alder reaction of both α-substituted and α-unsubstituted α,β-enals with various dienes. Hydroxy groups in optically active binaphthol derivatives and boron reagents with electron-withdrawing substituents were used as Bronsted acids and Lewis acids, respectively. Intramolecular Bronsted

  布朗斯台德酸辅助的手性路易斯酸 (BLA) 作为手性催化剂非常有效，可用于 α-取代和 α-未取代的 α,β-烯醛与各种二烯的对映选择性 Diels-Alder 反应。光学活性联萘酚衍生物中的羟基和具有吸电子取代基的硼试剂分别用作布朗斯台德酸和路易斯酸。手性 BLA 催化剂中的分子内布朗斯台德酸在加速 Diels-Alder 反应速率和产生高水平的对映选择性方面发挥了重要作用。特别是，由于手性 BLA 催化剂中羟基芳基在过渡态组装中的分子内氢键相互作用和有吸引力的 π-π 供体-受体相互作用，实现了优异的对映选择性。
• Homogeneous Model Complexes for Supported Rhenia Metathesis Catalysts
  作者：Yu-Ying Lai、Marc Bornand、Peter Chen

  DOI：10.1021/om300852s

  日期：2012.11.12

  A series of rhenium trioxo complexes (L-ReO3) was synthesized, characterized, and demonstrated to be active in olefin metathesis. The relationship between perrhenate (ReO4-), perrhenyl (ReO3+), and metathesis-active rhenium complexes (L-ReO3) was elucidated. Their chemical behavior can be tuned through the Lewis acid-base interaction. DFT calculations were performed for the metathesis reaction of L-ReO3 with norbornene, which demonstrates that electron-withdrawing substituents or ligands are beneficial for olefin metathesis activity. Moreover, a rhenium-alkylidene complex was synthesized, which can be activated by B(C6F5)(3) to afford an active metathesis catalyst. This be regarded as a homogeneous model of the hypothetical species present in the heterogeneous catalytic systems. The findings from the present study are consistent with our previous gas-phase studies and constitute the elucidation of the working principles for the metathesis-active rhenium species on the surface.