1-boronic acid ethylbenzene | 23171-20-2

• 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: 1-boronic acid ethylbenzene
• 英文别名: (1-Phenylethyl)boronic acid；1-phenylethylboronic acid
• CAS: 23171-20-2
• 化学式: C₈H₁₁BO₂
• 分子量: 149.985
• InChiKey: HSRYLENNPSXKCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-boronic acid ethylbenzene 在 氧气 作用下， 以 苯 为溶剂， 生成 (+-)-Dihydroxy-<1-phenyl-ethylperoxy>-boran
  参考文献：
  名称：

  除碳以外的其他元素的过氧化物。第十二部分。光学活性1-苯基乙基硼酸的自氧化

  摘要：

  苯中的旋光性1-苯基乙基硼酸与氧反应生成外消旋二羟基-1-苯基乙基过氧硼烷。该反应在NN（N）-二丁基二硫代氨基甲酸铜（II）和galvinoxyl的存在下显示出明显的诱导期。结论是，自氧化遵循自由基链机制，而不是通常假定的极性循环过程。

  DOI：

  10.1039/j29670000017
• 作为产物：
  描述：

  2-(1-phenyl-ethyl)-[1,3,6,2]dioxazaborocane 在 硫酸 作用下， 以 苯 为溶剂， 生成 1-boronic acid ethylbenzene
  参考文献：
  名称：

  除碳以外的其他元素的过氧化物。第十二部分。光学活性1-苯基乙基硼酸的自氧化

  摘要：

  苯中的旋光性1-苯基乙基硼酸与氧反应生成外消旋二羟基-1-苯基乙基过氧硼烷。该反应在NN（N）-二丁基二硫代氨基甲酸铜（II）和galvinoxyl的存在下显示出明显的诱导期。结论是，自氧化遵循自由基链机制，而不是通常假定的极性循环过程。

  DOI：

  10.1039/j29670000017

文献信息

• Alkyne Aminopalladation/Heck and Suzuki Cascades: An Approach to Tetrasubstituted Enamines
  作者：Finn J. Geffers、Florens R. Kurth、Peter G. Jones、Daniel B. Werz

  DOI：10.1002/chem.202103567

  日期：2021.10.25

  Internal alkynes have been used in combination with tosylamides and the Narasaka leaving group to form tetra(hetero)substituted enamines in an aminopalladation cascade reaction. The cascade was terminated either intramolecularly by a Heck reaction or intermolecularly in a Suzuki-type reaction with a boronic acid.

  内部炔烃已与甲苯磺酰胺和 Narasaka 离去基团组合使用，在氨基钯化级联反应中形成四（杂）取代的烯胺。该级联要么通过赫克反应在分子内终止，要么通过与硼酸的铃木型反应在分子间终止。
• Efficient cross-coupling of aryl/alkenyl triflates with acyclic secondary alkylboronic acids
  作者：Tengda Si、Bowen Li、Wenrui Xiong、Bin Xu、Wenjun Tang

  DOI：10.1039/c7ob02531a

  日期：——

  Aryl–secondary alkyl cross-coupling with aryl sulfonate esters as coupling partners remains a significant challenge. Efficient cross-coupling between aryl/alkenyl triflates and acyclic secondary alkylboronic acids is realized for the first time to provide a series of sterically congested acyclic secondary alkyl arenes/olefins in good to excellent yields. The employment of sterically bulky P,PO ligand L1/L2 is

  芳基-仲烷基与芳基磺酸酯作为偶联伙伴的交叉偶联仍然是一个巨大的挑战。首次实现了芳基/烯基三氟甲磺酸酯与无环仲烷基硼酸之间的有效交叉偶联，从而以良好或优异的收率提供了一系列空间上拥挤的无环仲烷基芳烃/烯烃。使用空间庞大的P，P O配体L1 / L2对于高收率和选择性至关重要。该方法实现了男性避孕药和PAF拮抗剂棉酚的关键中间体的简明和4步合成。
• Ligand-enabled Z-retentive Tsuji-Trost reaction
  作者：Jiandong Liu、Wen-Bin Cao、Shu-Li You

  DOI：10.1016/j.chempr.2024.02.006

  日期：2024.4

  The palladium-catalyzed allylic substitution (Tsuji-Trost) reaction is widely applied in organic synthesis, especially for the synthesis of stereochemically well-defined olefins. However, the synthesis of Z-olefins via the Tsuji-Trost reaction has been challenging due to the thermodynamic instability of the corresponding anti-π-allyl-palladium intermediate. Here, we report a ligand-enabled palladium-catalyzed

  钯催化的烯丙基取代（Tsuji-Trost）反应广泛应用于有机合成，特别是立体化学结构明确的烯烃的合成。然而，由于相应的反-π-烯丙基-钯中间体的热力学不稳定性，通过Tsuji-Trost反应合成Z-烯烃一直具有挑战性。在这里，我们报道了一种配体钯催化的Z保留烯丙基取代反应，该反应保留了Z烯烃的几何形状。由空间大的亚磷酰胺配体衍生的钯催化剂可以很好地区分亲核攻击步骤和 π-σ-π 异构化过程之间的反应速率。 Z保留烯丙基取代是由比异构化过程发生得快得多的亲核攻击引起的。已在低温下观察到反-π-烯丙基-钯中间体异构化为其顺式对应物。这些结果为手性Z-烯烃化合物的制备提供了一种有前景的方法。
• Reaction of Grignard Reagents with Diisopropylaminoborane. Synthesis of Alkyl, Aryl, Heteroaryl and Allyl Boronic Acids from Organoc(diisopropyl)aminoborane by a Simple Hydrolysis
  作者：Bakthan Singaram、Chris L. Murphy、Christopher L. Bailey、Jacob W. Clary、Scott Eagon、Naomi Gould

  DOI：10.3987/com-12-s(n)14

  日期：——

  Diisopropylaminoborane (BH2-N(iPr)(2)) is prepared by reacting lithium diisopropylaminoborohydride (iPr-LAB) with trimethylsilyl chloride (TMSCI). Aliphatic, aromatic, and heteroaromatic (diisopropylamino)boranes are readily synthesized at ambient temperature (0 degrees C) in 1 h by the reaction of Grignard reagents with (BH2-N(iPr)(2)). Two contending reaction pathways have tentatively been identified. During the mechanistic investigation, bromomagnesium diisopropylaminoborohydride was identified as a byproduct. This borylation reaction can be carried out under Barbier conditions, where (BH2-N(iPr)(2)) traps the in situ formed Grignard reagent from the corresponding organic halide and magnesium metal. Simple acid hydrolysis of the product organo(diisopropylamino)borane leads to the corresponding boronic acid in good to excellent yield.
• Discovery of 3<i>H</i>-Benzo[4,5]thieno[3,2-<i>d</i>]pyrimidin-4-ones as Potent, Highly Selective, and Orally Bioavailable Inhibitors of the Human Protooncogene Proviral Insertion Site in Moloney Murine Leukemia Virus (PIM) Kinases
  作者：Zhi-Fu Tao、Lisa A. Hasvold、Joel D. Leverson、Edward K. Han、Ran Guan、Eric F. Johnson、Vincent S. Stoll、Kent D. Stewart、Geoff Stamper、Nirupama Soni、Jennifer J. Bouska、Yan Luo、Thomas J. Sowin、Nan-Horng Lin、Vincent S. Giranda、Saul H. Rosenberg、Thomas D. Penning

  DOI：10.1021/jm900943h

  日期：2009.11.12

  Pim-1, Pim-2, and Pim-3 are a family of serine/threonine kinases which have been Found to be overexpressed in a variety of hematopoietic malignancies and solid tumors. Benzothienopyrimidinones were discovered as a novel class of Pim inhibitors that potently inhibit all three Pim kinases with subnanomolar to low single-digit nanomolar K-i values and exhibit excellent selectivity against a panel of diverse kinases. Protein crystal structures of the bound Pim-1 complexes of benzothienopyrimidinones 3b (PDB code 3JYA), 6e (PDB code 3JYO), and 12b (PDB code 3JXW) were determined and used to guide SAR studies. Multiple compounds exhibited potent antiproliferative activity in K562 and MV4-11 cells with submicromolar EC50 values. For example, compound 14j inhibited the growth of K562 cells with an EC50 value of 1.7 mu M and showed K-i values of 2, 3, and 0.5 nM against Pim-1, Pim-2, and Pim-3, respectively. These novel Pim kinase inhibitors efficiently interrupted the phosphorylation of Bad in both K562 and LnCaP-Bad cell lines, indicating that their potent biological activities are mechanism-based. The pharmacokinetics of 14j was studied in CD-1 mice and shown to exhibit bioavailability of 76% after oral dosing. ADME profiling of 14j suggested a long half-life in both human and mouse liver microsomes, good permeability, modest protein bin-ling, and no CYP inhibition below 20 mu M concentration.