(3,5-diisopropylphenyl)boronic acid | 263397-82-6

• 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: (3,5-diisopropylphenyl)boronic acid
• 英文别名: 3,5-diisopropylphenylboronic acid；3,5-diisopropylboronic acid；[3,5-di(propan-2-yl)phenyl]boronic acid
• CAS: 263397-82-6
• 化学式: C₁₂H₁₉BO₂
• 分子量: 206.093
• InChiKey: LHMPHKBDIKUKRC-UHFFFAOYSA-N

物化性质

• 熔点：
  142-144 °C
• 沸点：
  322.8±52.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.61
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  (3,5-diisopropylphenyl)boronic acid 在 四(三苯基膦)钯 盐酸 、 tin 、 sodium carbonate 、 溶剂黄146 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 30.5h， 生成 1-(3,5-diisopropylphenyl)-9-anthrone
  参考文献：
  名称：

  涉及乙炔碳的旋转异构体 VI。双（1-苯基-9-蒽基）乙炔的合成、结构和动态立体化学：无环二芳炔中乙炔轴的高度受限旋转

  摘要：

  一些在 1-位具有取代苯基（4-Me、4-iPr、4-tBu、3-iPr、3,5-iPr2）的空间拥挤的二（9-蒽基）乙炔通过对应的...

  DOI：

  10.1246/bcsj.78.917
• 作为产物：
  描述：

  3,5-二异丙基溴苯 在 正丁基锂 、 硫酸 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 2.5h， 以50%的产率得到(3,5-diisopropylphenyl)boronic acid
  参考文献：
  名称：

  Monofunctional Hyperbranched Ethylene Oligomers

  摘要：

  The neutral kappa N-2,O-salicylaldiminato Ni(II) complexes [kappa N-2,O-{(2,6-(3',5'-R2C6H3)(2)C6H3-N=C(H)-(3,5-I-2-2-O-C6H2)}]NiCH3(pyridine)] (1a-pyr, R = Me; 1b-pyr, R = Et; 1c-pyr, R = iPr) convert ethylene to hyperbranched low-molecular-weight oligomers (M-n ca. 1000 g mol(-1)) with high productivities. While all three catalysts are capable of generating hyperbranched structures, branching densities decrease significantly with the nature of the remote substituent along Me > Et > iPr and oligomer molecular weights increase. Consequently, only 1a-pyr forms hyperbranched structures over a wide range of reaction conditions (ethylene pressure 5-30 atm and 20-70 degrees C). An in situ catalyst system achieves similar activities and identical highly branched oligomer microstructures, eliminating the bottleneck given by the preparation and isolation of Ni Me catalyst precursor species. Selective introduction of one primary carboxylic acid ester functional group per highly branched oligoethylene molecule was achieved by isomerizing ethoxycarbonylation and alternatively cross metathesis with ethyl acrylate followed by hydrogenation. The latter approach results in complete functionalization and no essential loss of branched oligomer material and molecular weight, as the reacting double bonds are close to a chain end. Reduction yielded a monoalcohol-functionalized oligomer. Introduction of one reactive epoxide group per branched oligomer occurs completely and selectively under mild conditions. All reaction steps involved in oligomerization and monofunctionalization are efficient and readily scalable.

  DOI：

  10.1021/ja411945n

文献信息

• [EN] CATALYSTS<br/>[FR] CATALYSEURS
  申请人：BOREALIS AG

  公开号：WO2018091684A1

  公开（公告）日：2018-05-24

  A complex of formula (I) wherein M is zirconium or hafnium; each X independently is a sigma ligand; L is a divalent bridge selected from -R'2C-, -R'2C-CR'2-, -R'2Si-, -R'2Si-SiR'2-, -R'2Ge-, wherein each R' is independently a hydrogen atom or a C1-C20-hydrocarbyl group optionally containing one or more silicon atoms or heteroatoms of Group 14-16 of the periodic table or fluorine atoms, and optionally two R' groups taken together can form a ring; R2 and R2' are each independently a C1-C20 hydrocarbyl group, -OC1- hydrocarbyl group or -SC1-20 hydrocarbyl group; R5 is a -OC1-20 hydrocarbyl group or -SC1-20 hydrocarbyl group, said R5 group being optionally substituted by one or more halo groups; R5' is hydrogen or a C1-20 hydrocarbyl group; -OC1-20 hydrocarbyl group or -SC1-20 hydrocarbyl group; said C1-20 hydrocarbyl group being optionally substituted by one or more halo groups; R6 and R6' are each independently a C1-20 hydrocarbyl group; -OC1-20 hydrocarbyl group or -SC1-20 hydrocarbyl group; each R1 and R1' are independently -CH2Rx wherein Rx are each independently H, or a C1-20 hydrocarbyl group, optionally containing heteroatoms.

  式中M为锆或铪；每个X独立地是一个σ配体；L是一个二价桥，选自-R'2C-、-R'2C-CR'2-、-R'2Si-、-R'2Si-SiR'2-、-R'2Ge-，其中每个R'独立地是一个氢原子或一个C1-C20的烃基团，可选地包含一个或多个硅原子或周期表中第14-16族的杂原子或氟原子，并且可选地两个R'基团一起可以形成一个环；R2和R2'各自独立地是一个C1-C20烃基团、-OC1-烃基团或-SC1-20烃基团；R5是一个-OC1-20烃基团或-SC1-20烃基团，所述R5基团可被一个或多个卤素取代；R5'是氢或一个C1-20烃基团；-OC1-20烃基团或-SC1-20烃基团；所述C1-20烃基团可被一个或多个卤素取代；R6和R6'各自独立地是一个C1-20烃基团；-OC1-20烃基团或-SC1-20烃基团；每个R1和R1'各自独立地为-CH2Rx，其中Rx各自独立地为H，或一个C1-20烃基团，可选地含有杂原子。
• Syntheses of Sterically Hindered Pyridinium Phenoxides as Model Compounds in Nonlinear Optics
  作者：Vincent Diemer、Hélène Chaumeil、Albert Defoin、Alain Fort、Alex Boeglin、Christiane Carré

  DOI：10.1002/ejoc.200600030

  日期：2006.6

  increase in the twist angle between the two aromatic rings leads to an enhancement of the NLO properties. In order to confirm this feature experimentally, it was necessary to prepare a series of new hindered pyridinium phenoxides. Their efficient syntheses by Suzuki cross-coupling reactions are described herein.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

  具有 π 共轭系统的非中心对称分子，其中包括苯酚吡啶等推挽分子，由于其非线性光学 (NLO) 特性，是一类有前途的新型光电子材料。建模研究表明，两个芳环之间扭曲角的增加导致 NLO 性能的增强。为了通过实验证实这一特征，有必要制备一系列新的受阻吡啶酚盐。本文描述了它们通过 Suzuki 交叉偶联反应的有效合成。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
• Introducing NacNac-Like Bis(4,6-isopropylbenzoxazol-2-yl)methanide in s-Block Metal Coordination
  作者：Ingo Koehne、Nico Graw、Thorsten Teuteberg、Regine Herbst-Irmer、Dietmar Stalke

  DOI：10.1021/acs.inorgchem.7b02276

  日期：2017.12.18

  of bulky methanides in metal coordination is exceeded by the synthesis of the versatile and promising bis(4,6-isopropylbenzoxazol-2-yl)methane (7) ligand platform. As an enhancement in this class of ligands, isopropyl (iPr) substituents as steric-demanding groups have been successfully introduced in proximity to the coordination pocket, mimicking the shielding abilities of the ubiquitous NacNac ligand

  在这项工作中，多功能和有前途的双（4,6-异丙基苯并恶唑-2-基）甲烷（7）配体平台的合成超出了金属配合物中大体积甲烷化物的领域。作为这类配体的增强，已经成功地在配位袋附近引入了异丙基（i Pr）取代基作为空间需求基团，模仿了无处不在的NacNac配体支架的屏蔽能力，从而改善了配位s的空间保护。嵌段金属阳离子。埋入体积百分比（％V bur）计算以及电子结构分析，与其他选定的甲烷化物和二酮化物相比，光可以掩蔽配体的屏蔽和电子功能。在用各种不同的第1组和第2组金属化剂去质子化后，获得了母体去质子化的单阴离子配体7的一排新型s嵌段金属络合物，并在结构和光谱上进行了表征。特别地，在这种情况下，碱金属前体配合物[Li（THF）2 （4,6- i Pr-NCOC 6 H 2）2 CH}]（8）和[K μ-（4,6 -我镨NCOC 6 ħ 2）2CH}] ∞（9）以及碱土金属化合物[MgCl（THF）2
• Rotational isomerism involving an acetylenic carbon. Part 5: Restricted rotation about acetylenic axis in sterically crowded bis(1-phenyl-9-anthryl)ethynes
  作者：Shinji Toyota、Toshiaki Makino

  DOI：10.1016/j.tetlet.2003.08.079

  日期：2003.10

  di-9-anthrylethyne derivative with 3,5-iPr2-phenyl groups at 1-position showed a barrier to rotation about the acetylenic axis of 18.0 kcal mol−1 based on a dynamic NMR study, which is an extremely high value for acyclic diarylethynes. The mechanism of the dynamic stereochemistry and the substituent effect on the rotational barrier are discussed.

  根据动态NMR研究，标题为在1位具有3,5- i Pr 2-苯基的空间拥挤的di-9-蒽乙炔衍生物显示出绕炔键轴旋转的障碍为18.0 kcal mol -1。无环二芳基乙炔具有极高的价值。讨论了动态立体化学的机理以及取代基对旋转势垒的影响。
• Synthesis of substituted (N,C) and (N,C,C) Au(<scp>iii</scp>) complexes: the influence of sterics and electronics on cyclometalation reactions
  作者：Knut T. Hylland、Inga L. Schmidtke、David S. Wragg、Ainara Nova、Mats Tilset

  DOI：10.1039/d2dt00371f

  日期：——

  cyclometalation at Au(III) to take place via an electrophilic aromatic substitution-type mechanism. The formation of Au(III) pincer complexes from tridentate (N,C,C) ligands was investigated by synthesis and DFT calculations, in order to assess the feasibility of C(sp3)–H bond activation as a synthetic pathway to (N,C,C) cyclometalated Au(III) complexes. It was found that C(sp3)–H bond activation is feasible for

  环金属化 Au( III ) 配合物因其催化、药用和光物理特性而备受关注。在此，我们描述了通过环金属化途径合成 (N,C)Au(OAc F ) 2 (OAc F = 三氟乙酸酯) 和 (N,C,C)AuOAc F类型的衍生物，其中 (N,C) 和(N,C,C) 是螯合 2-芳基吡啶配体。通过在一个或两个环上用电子供体或受体取代基取代 2-芳基吡啶核来探索合成的范围。值得注意的是，从相应的配体和 Au(OAc) 3中一步即可获得多种功能化的 Au( III ) 配合物，消除了对有机汞中间体的需求，这通常用于类似的合成。使用 DFT 计算、 15 N NMR 光谱和单晶 X 射线衍射分析评估配体骨架中的取代基对所得配合物的影响。结合自然电荷分析的实验研究发现，(N,C) 配体的电子特性与其进行环金属化的能力之间存在相关性，表明 Au( III ) 处的环金属化是通过亲电子芳香取代型机制发生的.