2,5-bis(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)thiophene | 26076-47-1

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 2,5-bis(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)thiophene
• 英文别名: 5,5,5',5'-tetramethyl-2,2'-thiophene-2,5-diyl-bis-[1,3,2]dioxaborinane；2-[5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)thiophen-2-yl]-5,5-dimethyl-1,3,2-dioxaborinane
• CAS: 26076-47-1
• 化学式: C₁₄H₂₂B₂O₄S
• 分子量: 308.014
• InChiKey: YWHICQKXLXQHLD-UHFFFAOYSA-N

物化性质

• 熔点：
  155-156 °C
• 沸点：
  448.4±30.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.28
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  65.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,5-bis(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)thiophene 、 1-甲基苯基乙酮 在 RuH₂(CO)(PPh₃)₃ 作用下， 以 频哪酮 为溶剂， 反应 24.0h， 以38%的产率得到
  参考文献：
  名称：

  通过苯乙酮与芳烃二硼酸酯的 C-H 芳基化方便地合成二苯并 [a,h] 蒽和 Picenes

  摘要：

  已经开发了一种使用钌催化的芳族酮的区域选择性 C-H 芳基化合成二苯并 [a,h] 蒽和 picenes 的新方法。苯乙酮衍生物

  DOI：

  10.1246/cl.2011.300
• 作为产物：
  描述：

  2,5-二硼酸噻吩 、 2,2-二甲基-1,3-丙二醇 以 四氢呋喃 为溶剂， 反应 1.0h， 以70.7%的产率得到2,5-bis(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)thiophene
  参考文献：
  名称：

  Effect of molecular weight on electronic, electrochemical and spectroelectrochemical properties of poly(3,3″-dioctyl-2,2′∶5′,2″-terthiophene)

  摘要：

  聚(3,3″-二辛基-2,2′-∥5′,2″-三噻吩)，通过与FeCl3的氧化聚合从相应单体获得，已被分级为五个具有降低聚分散度的分级，覆盖了1.50 kDa到10.50 kDa的Mn范围（与聚苯乙烯标准相比测量）。研究了Mn对光谱、电化学、光谱电化学和电输运特性的影响。随着Mn的增加，中性聚合物中源于π–π*跃迁的带出现明显的红移，并且对于两个最高分子量的分级显示出清晰的振动结构。从循环伏安图中确定的氧化掺杂起始点随着分子量的增加而向较低电位移动。对于掺杂诱导的近红外带也观察到类似的趋势，随着分子量的增加，带向较低能量（较高波长）移动，并在光谱电化学实验中出现在较低电位。最后，对在相同条件下制造的两种分子量不同的聚合物分级的场效应晶体管（FET）迁移率进行比较，发现Mn约增加四倍（从2.40 kDa到10.50 kDa）导致载流子迁移率增加两个数量级（从μsat = 4 × 10⁻⁵ cm² V⁻¹ s⁻¹到μsat = 2 × 10⁻³ cm² V⁻¹ s⁻¹）。获得的结果强调了在制备基于聚(3,3″-二辛基-2,2′-∥5′,2″-三噻吩)的电子和电化学器件时，对大分子参数控制的重要性。

  DOI：

  10.1039/b605504d

文献信息

• Organoboron compounds. Part VIII. Aliphatic and aromatic diboronic acids
  作者：I. G. C. Coutts、H. R. Goldschmid、O. C. Musgrave

  DOI：10.1039/j39700000488

  日期：——

  Diboronic acids (HO)2B·R·B(OH)2(where R = polymethylene, arylene, or thiophen-2,5-diyl) are prepared by reactions of methyl borate with difunctional Grignard reagents and are characterised by the formation of cyclic esters with various diols. The polymethylenediboronic acids are much more resistant to aerial oxidation than are the corresponding alkylboronic acids. All the diboronic acids undergo dehydration

  二硼酸（HO）2 B·R·B（OH）2（其中R =聚亚甲基，亚芳基或噻吩-2,5-二基）是通过硼酸甲酯与双功能格氏试剂反应制备的，其特征在于与各种二醇的环酯。聚亚甲基二硼酸比相应的烷基硼酸更耐空气氧化。所有的二硼酸都经过脱水反应生成相应的聚合酸酐，其中芳族化合物的温度要求> 230°。描述了导致脱硼或形成胺络合物的反应。噻吩-2,5-二基二硼酸经阮内镍处理后进行氢解，得到四亚甲基二硼酸。
• Zero-Valent Metals Accelerate the Neopentylglycolborylation of Aryl Halides Catalyzed by NiCl₂-Based Mixed-Ligand Systems
  作者：Pawaret Leowanawat、Ana-Maria Resmerita、Costel Moldoveanu、Chi Liu、Na Zhang、Daniela A. Wilson、Lisa M. Hoang、Brad M. Rosen、Virgil Percec

  DOI：10.1021/jo101718v

  日期：2010.11.19

  The highly active mixed-ligand catalytic system NiCl2(dppp)/dppf combined with the reducing effect of zerovalent Zn and of other metals was used to demonstrate a method for the dramatic acceleration of the rate and for the enhancement of the yield of Ni-catalyzed neopentylglycolborylation of aryl halides A diversity of electron-rich and electron-deficient aryl iodides, bromides, and chlorides were efficiently neopentylglycolborylated, typically in 1 h or less This acceleration is particularly remarkable for the generally less reactive aryl bromides and chlorides and for all ortho-substituted aryl halides By accelerating the rate of borylation and reducing its reaction time to complete conversion, pathways leading to protodeborylated or hydrodehalogenated side products have a reduced impact on the outcome of the overall reaction Although Zn powder was the reducing agent of choice, compatibility of this technique with more readily recoverable Zn chips, as well as other metals such as Mn, Mg, Fe, Al, and Ca, has demonstrated the broad scope of this synthetic method
• Neopentylglycolborylation of <i>ortho</i>-Substituted Aryl Halides Catalyzed by NiCl₂-Based Mixed-Ligand Systems
  作者：Costel Moldoveanu、Daniela A. Wilson、Christopher J. Wilson、Pawaret Leowanawat、Ana-Maria Resmerita、Chi Liu、Brad M. Rosen、Virgil Percec

  DOI：10.1021/jo101023t

  日期：2010.8.20

  NiCl2-based mixed-ligand systems were shown to be very effective catalysts for the neopentylglycolborylation of aryl iodides, bromides, and chlorides bearing electron-rich and electron-deficient ortho-substituents. Although NiCl2-based single-ligand catalytic systems were able to mediate neopentylglycolborylation of selected substrates, they were not as effective for all substrates, highlighting the value of the mixed-ligand concept. Optimization of the Ni(II)-catalyzed neopentylglycolborylation of 2-iodoanisole and methyl 2-iodobenzoate demonstrated that, while the role of ligand and coligand in the conversion of Ni(II) precatalyst to Ni(0) active catalyst cannot be ignored, a mixed-ligand complex is likely present throughout the catalytic cycle. In addition, protodeborylation and hydrodehalogenation were demonstrated to be the predominant side reactions of borylation of ortho-substituted aryl halides containing the electron-deficient carboxylate substituents. Ni(II) complexes in the presence of H2O and Ni(0) are responsible for the catalysis of these side reactions.