3-(tert-butyl)-2-hydroxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde | 945629-66-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(tert-butyl)-2-hydroxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde
• 英文别名: 3-Tert-butyl-2-hydroxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde
• CAS: 945629-66-3
• 化学式: C₁₇H₂₅BO₄
• 分子量: 304.194
• InChiKey: CMOARUJIOPKYNB-UHFFFAOYSA-N

物化性质

• 沸点：
  388.6±42.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(tert-butyl)-2-hydroxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde 在 四(三苯基膦)钯 sodium carbonate 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 H2[HSX*t-Bu-COOH]
  参考文献：
  名称：

  Catalase and Epoxidation Activity of Manganese Salen Complexes Bearing Two Xanthene Scaffolds

  摘要：

  A series of manganese Hangman salen ligand platforms functionalized by tert-butyl groups in the 3 and 3' positions using the Suzuki cross-coupling methodology are presented. The Hangman platforms support multielectron chemistry mediated by proton-coupled electron transfer (PCET), as demonstrated by their ability to promote the catalytic disproportionation of hydrogen peroxide to oxygen and water via a high-valent metal oxo. The addition of the steric groups to the salen macrocycle leads to enhanced catalase activity by circumventing side reactions that sequester the catalyst off pathway. The stereochemistry imposed by the cyclohexanediamine backbone of the salen platform is revealed by the epoxidation of 1,2-dihydronapthalene by a variety of oxidants. Improved enantiomeric excess and catalase activity as compared to sterically unmodified counterparts establishes the efficacy of the tert-butyl groups in promoting PCET catalysis on the Hangman platform.

  DOI：

  10.1021/ja070358w
• 作为产物：
  描述：

  2-叔丁基苯酚 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 三正丁胺 、 溴 、 potassium acetate 、 四氯化锡 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 18.25h， 生成 3-(tert-butyl)-2-hydroxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde
  参考文献：
  名称：

  四组分锌卟啉/锌沙芬纳米转子

  摘要：

  离轴超分子转子由四个组件组成：带有四个菲咯啉位的锌卟啉基定子和带有DABCO和四个铜（I）离子的锌-钠酚基转子自组装，以在转子中提供ROT-2转子。定量产量。DABCO用作转子和定子之间的连接轴，而转子则通过其两个吡啶末端（N py →[Cu（phen）] +）另外连接到定子的两个负载铜（I）的菲咯啉位。对于热激活旋转，N py →[Cu（phen）] +相互作用必须被切断。由于旋转的高能垒，ROESY监控了慢动作。根据计算的见解，降低的速度（k 298 = 0.2 s -1）在转子的基态稳定方面得到了合理化。进行了额外的VT 1 H-NMR研究，以研究DABCO的运动，该DABCO夹在锌卟啉锌和锌丹参酮之间。基于由产生非对映体环境的四边形所引起的不对称，合理地诊断了双子DABCO质子的诊断分裂。计算结果以极好的一致性再现了实验NMR。

  DOI：

  10.1039/c7dt01323j

文献信息

• Conformationally restricted dynamic supramolecular catalysts for substrate-selective epoxidations
  作者：Esmaeil Sheibani、Kenneth Wärnmark

  DOI：10.1039/c2ob06859a

  日期：——

  A second generation of a substrate-selective dynamic supramolecular catalytic system consisting of a catalyst part and a receptor part, connected by a hydrogen-bonding motif, has been realized based on rational design. The results from analyses of the equilibrium mixture of the species generated by the components of the first generation system led us to selectively lock the cisoid conformation of the catalyst part to increase the amount of the substrate-selective catalytic cavity in the equilibrium mixture. This was realized by strapping the catalyst part by organic synthesis. This strapping led to an increase in substrate selectivity in the pair-wise competitive epoxidations of pyridyl- vs. phenyl-appended styrenes and pyridyl- vs. phenyl-appended stilbenes of both Z- and E- configuration compared to the first generation system, reaching 3.4 : 1 as the highest substrate selectivity for Z-mono-pyridyl-stilbene (27a) vs. the corresponding all-carbon analogue (28a) and for E-dipyridyl-stilbene (26b) vs. the corresponding all-carbon analogue (28b), respectively.

  基于合理设计的理念，我们实现了一种第二代底物选择性动态超分子催化系统，该系统由催化部分和受体部分组成，通过氢键连接。通过对第一代系统生成物种的平衡混合物进行分析，我们得出了将催化部分的顺式构象选择性锁定以增加平衡混合物中底物选择性催化腔数量的结论。通过有机合成的方法对催化部分进行约束，实现了这一目标。与第一代系统相比，这种约束导致了在吡啶基与苯基修饰的苯乙烯以及吡啶基与苯基修饰的Z型和E型二苯乙烯的配对竞争环氧化反应中，底物选择性的提高，最高达到了3.4:1的选择性，分别对应于Z型单吡啶基二苯乙烯（27a）与相应的全碳类似物（28a）以及E型二吡啶基二苯乙烯（26b）与相应的全碳类似物（28b）。
• New Chiral Calixsalen Chromium Complexes: Recyclable Asymmetric Catalysts
  作者：Anaïs Zulauf、Mohamed Mellah、Emmanuelle Schulz

  DOI：10.1002/chem.201001012

  日期：——

  ylenediamine (salen) polymer has been prepared by a condensation reaction between a thiophenedisalicyladehyde derivative and (S,S)‐cyclohexane‐1,2‐diamine. This polymeric compound was demonstrated to possess a cyclic structure with two to five repetitive units. The addition of chromium(II) salts led to the generation of a chiral catalyst that could be recovered as an insoluble powder. The performance

  的手性Ñ，Ñ ' -双（亚水杨基）乙二胺（沙仑）聚合物已经制备由thiophenedisalicyladehyde衍生物和（之间的缩合反应小号，小号）-环己烷-1,2-二胺。证明该聚合化合物具有带有两个至五个重复单元的环状结构。铬（II）盐的添加导致手性催化剂的产生，该手性催化剂可以以不溶性粉末的形式回收。在各种转化中，特别是在异质条件下促进亲核环氧化物开环的能力中，检验了这种新型杯盖型催化剂的性能。与通过使用类似的线性聚合物获得的目标产物相比，以高收率和改进的选择性获得了目标产物。环状结构中催化位点的排列可能更适合于这种苛刻反应的必要的协同双金属途径。该催化剂可以成功地再循环。
• Cooperative Activation in the Hydrolytic Kinetic Resolution of Epoxides by a Bis-Cobalt(III)salen-Calix[4]arene Hybrid
  作者：Sander J. Wezenberg、Arjan W. Kleij

  DOI：10.1002/adsc.200900673

  日期：2010.1.4

  A chiral, bimetallic cobalt(III)salen‐calix[4]arene hybrid structure was prepared and tested in the hydrolytic kinetic resolution (HKR) of racemic epoxides. Kinetic studies have revealed that the two catalytic units on the upper rim of the calixarene scaffold are able to activate the reactants in a cooperative and primarily intramolecular mode. High enantioselective behaviour was observed and besides

  制备了手性双金属钴（III）salen-calix [4]芳烃杂化结构，并在外消旋环氧化物的水解动力学拆分（HKR）中进行了测试。动力学研究表明，杯芳烃支架上缘上的两个催化单元能够以协作且主要是分子内的方式活化反应物。观察到高对映选择性，并且与单金属参比配合物相比，双金属催化剂具有更高的稳定性。
• PCET-Based Ligand Limits Charge Recombination with an Ir(III) Photoredox Catalyst
  作者：Hannah Sayre、Hunter H. Ripberger、Emmanuel Odella、Anna Zieleniewska、Daniel A. Heredia、Garry Rumbles、Gregory D. Scholes、Thomas A. Moore、Ana L. Moore、Robert R. Knowles

  DOI：10.1021/jacs.1c01701

  日期：2021.8.25

  Upon photoinitiated electron transfer, charge recombination limits the quantum yield of photoredox reactions for which the rates for the forward reaction and back electron transfer are competitive. Taking inspiration from a proton-coupled electron transfer (PCET) process in Photosystem II, a benzimidazole-phenol (BIP) has been covalently attached to the 2,2′-bipyridyl ligand of [Ir(dF(CF3)ppy)2(bpy)][PF6]

  在光引发电子转移时，电荷复合限制了光氧化还原反应的量子产率，在该反应中，正向反应和反向电子转移的速率具有竞争力。受光系统 II 中质子耦合电子转移 (PCET) 过程的启发，苯并咪唑-苯酚 (BIP) 已共价连接到 [Ir(dF(CF 3 )ppy) 2 ( bpy)][PF 6 ] (dF(CF 3 )ppy = 2-(2,4-二氟苯基)-5-(三氟甲基)吡啶；bpy = 2,2'-联吡啶)。[Ir(dF(CF 3 )ppy) 2 (BIP-bpy)][PF 6 的激发] 光催化剂导致分子内 PCET 与氧化 BIP 形成电荷分离状态。随后通过电荷分离物质的还原部分还原作为底物替代物的甲基紫精 (MV 2+ ) 表明 BIP 的包含显着减慢了电荷重组速率。在光催化邻苯二甲酰亚胺酯还原中，约 24 倍较慢的电荷复合效应导致反应量子效率增加 2 倍以上。
• 색재 조성물, 감광성 수지 조성물, 감광재, 컬러필터, 및 디스플레이 장치
  申请人：LG CHEM, LTD. 주식회사 엘지화학(120010134563) Corp. No ▼ 110111-2207995BRN ▼107-81-98139

  公开号：KR20200069730A

  公开（公告）日：2020-06-17

  본 명세서는 화학식 1로 표시되는 화합물을 포함하는 색재 조성물 및 이를 포함하는 감광성 수지 조성물, 감광재, 컬러필터 및 디스플레이 장치를 제공한다.

  本规范提供了包含标记为化学式1的化合物的颜料组合物，以及包含该颜料组合物的感光树脂组合物、感光剂、彩色滤光片和显示器件。