(Z)-4,4,5,5-tetramethyl-2-(4-styrylphenyl)-1,3,2-dioxaborolane | 1221823-28-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (Z)-4,4,5,5-tetramethyl-2-(4-styrylphenyl)-1,3,2-dioxaborolane
• 英文别名: (Z)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)stilbene；4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)stilbene；4,4,5,5-tetramethyl-2-[4-[(Z)-2-phenylethenyl]phenyl]-1,3,2-dioxaborolane
• CAS: 1221823-28-4
• 化学式: C₂₀H₂₃BO₂
• 分子量: 306.212
• InChiKey: HNKMMQPUGYZDTK-KHPPLWFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.16
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-(苯基乙炔基)苯硼酸频哪醇酯 在 nickel(II) nitrate hexahydrate 、 氢气 作用下， 以 乙腈 为溶剂， 120.0 ℃ 、3.0 MPa 条件下， 反应 15.0h， 以91%的产率得到(Z)-4,4,5,5-tetramethyl-2-(4-styrylphenyl)-1,3,2-dioxaborolane
  参考文献：
  名称：

  镍催化炔烃加氢立体发散合成E-和Z-烯烃

  摘要：

  开发了一种使用镍催化剂将炔烃立体发散氢化为E-和Z-烯烃的便捷方案。简单的Ni(NO 3 ) 2 ⋅6 H 2 O作为催化剂前体形成活性纳米粒子，可有效地对多种炔烃进行半加氢，并且对Z-烯烃具有高选择性（ Z / E > 99:1）。添加特定的多齿配体（三磷、四磷）后，所得分子催化剂对E-烯烃产物具有高度选择性（E/Z > 99:1）。机理研究表明Z-烯烃选择性催化剂是非均相的，而E-烯烃选择性催化剂是均相的。在后一种情况下，炔烃首先被氢化为Z-烯烃，随后异构化为E-烯烃。该提议得到了密度泛函理论计算的支持。这种合成方法被证明普遍适用于超过 40 个例子，并且可扩展到多克规模的实验。

  DOI：

  10.1002/cssc.201900784

文献信息

• Facile Regio- and Stereoselective Hydrometalation of Alkynes with a Combination of Carboxylic Acids and Group 10 Transition Metal Complexes: Selective Hydrogenation of Alkynes with Formic Acid
  作者：Ruwei Shen、Tieqiao Chen、Yalei Zhao、Renhua Qiu、Yongbo Zhou、Shuangfeng Yin、Xiangbo Wang、Midori Goto、Li-Biao Han

  DOI：10.1021/ja2069246

  日期：2011.10.26

  highly stereo- and regioselective hydrometalation of alkynes generating alkenylmetal complex is disclosed for the first time from a reaction of alkyne, carboxylic acid, and a zerovalent group 10 transition metal complex M(PEt(3))(4) (M = Ni, Pd, Pt). A mechanistic study showed that the hydrometalation does not proceed via the reaction of alkyne with a hydridometal generated by the protonation of a

  通过炔烃、羧酸和零价族 10 过渡金属络合物 M(PEt(3))(4) (M =镍、钯、铂）。一项机理研究表明，氢金属化不是通过炔烃与由羧酸与 Pt(PEt(3))(4) 质子化产生的氢化金属反应进行的，而是通过炔烃配位金属络合物与酸。这一发现阐明了长期以来提出的反应机制，该机制通过生成烯基钯中间体和随后在由 Brφnsted 酸和 Pd(0) 配合物的组合催化的各种反应中转化该配合物来进行。
• [EN] NOVEL LIPOGENIC INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS LIPOGÈNES INÉDITS ET LEURS UTILISATIONS
  申请人：EINSTEIN COLL MED

  公开号：WO2012112670A1

  公开（公告）日：2012-08-23

  The present invention provides resveratrol-based boron-containing analog! methods of use thereof in treatment of dyslipidemias and cancer.

  这项发明提供了基于白藜芦醇的含硼类似物！以及在治疗血脂异常和癌症中的使用方法。
• An Amine-Assisted Ionic Monohydride Mechanism Enables Selective Alkyne <i>cis</i>-Semihydrogenation with Ethanol: From Elementary Steps to Catalysis
  作者：Zhidao Huang、Yulei Wang、Xuebing Leng、Zheng Huang

  DOI：10.1021/jacs.1c01472

  日期：2021.3.31

  protonolysis of the Ir–C(vinyl) bond. Instead, mechanistic data are consistent with an anion-involved alcoholysis pathway involving ionization of (NCP)IrCl(vinyl) via EtOH-for-Cl substitution and reversible protonation of Cl– ion with an Ir(III)-bound EtOH, followed by β-H elimination of the ethoxy ligand and C(vinyl)–H reductive elimination. The use of an amine is key to the monohydride mechanism by promoting

  Z-烯烃在炔烃半加氢反应中的选择性合成取决于催化剂对起始原料和产物的反应性差异。在这里，我们报告了通过配位诱导的离子一氢化物机制用乙醇对炔烃进行Z选择性半氢化。EtOH 配位驱动的 Cl –在钳形 Ir(III) 氢氯化物络合物 (NCP)IrHCl ( 1 ) 中解离形成阳离子一氢化物，[(NCP)IrH(EtOH)] + Cl –，它选择性地与炔烃反应相应的Z-烯烃，从而克服竞争性热力学主导烯烃Z - E异构化和过度还原。然而，建立催化循环的挑战在于醇解步骤；炔烃插入产物 (NCP)IrCl(乙烯基) 与 EtOH 的反应确实发生，但非常缓慢。令人惊讶的是，醇解不是通过 Ir-C（乙烯基）键的直接质子分解进行的。相反，机理数据与涉及阴离子的醇解途径一致，包括 (NCP)IrCl(vinyl) 通过 EtOH-for-Cl 取代电离和 Cl -离子与 Ir(III) 结合的 EtOH 的可逆质子化，然后是
• Synthesis of Pinacolylboronate-Substituted Stilbenes and their application to the synthesis of boron capped polyenes
  作者：Bhaskar C. Das、Sakkarapalayam M. Mahalingam、Sasmita Das、Narayan S. Hosmane、Todd Evans

  DOI：10.1016/j.jorganchem.2015.08.007

  日期：2015.12

  A series of novel 4,4,5,5-tetramethyl-2-(4-substitutedstyrylphenyl)-1,3,2 dioxaborolane derivatives has been synthesized. 4-(4,4,5,5-tetramethyl-1,3,2-dioxaboratophenyl)-methyl triphenylphosphonium bromide (4) was treated with 3 equiv of tBuONa, various aldehydes in the presence of DMF, and stirred at room temperature 4-6 h to yield the corresponding boron containing stilbene derivatives 1 a-n in 71 -94% yields. A one-pot protocol transformation has also been developed and used this methodology to synthesize boron containing resveratrol analogues. Simple and clean reactions, high yield of the products are the salient features of this methodology. We used this reaction to synthesize the boron capped polyenes. These boron containing polyene systems are potential intermediate to synthesize conjugated polyene as new material for LCD (Liquid Crystal Display) technology. The biological testing of these compounds is currently underway to identify potential therapeutic for Neurodegenerative diseases. (C) 2015 Elsevier B.V. All rights reserved.
• Design and synthesis of novel pinacolylboronate containing combretastatin ‘antimitotic agent’ analogues
  作者：Bhaskar C. Das、Sakkarapalayam M. Mahalingam、Todd Evans

  DOI：10.1016/j.tetlet.2009.04.003

  日期：2009.6

  We developed a procedure to synthesize pinacolyl boronate containing stilbene derivatives and used this procedure to synthesize boron-containing combretastatin analogues. The key step involves the Wittig reaction of the ylide 4-(4,4,5,5-tetramethyl-1,3,2-dioxaboratophenyl)-methyl triphenylphosphonium bromide 11 with 3,4,5-trimethoxy benzaldehyde in the presence of (1)BuONa in DMF, providing 88% yield. We are now in a position to evaluate the biological activity of these derivatives as modulators of TGF-beta signaling pathways. (C) 2009 Elsevier Ltd. All rights reserved.