1,4-bis(trimethylsilyl)-2,5-dimethoxybenzene | 92669-95-9

• 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: 1,4-bis(trimethylsilyl)-2,5-dimethoxybenzene
• 英文别名: (2,5-dimethoxy-4-trimethylsilylphenyl)-trimethylsilane
• CAS: 92669-95-9
• 化学式: C₁₄H₂₆O₂Si₂
• 分子量: 282.53
• InChiKey: PUCSYIBTZNHBKA-UHFFFAOYSA-N

物化性质

• 熔点：
  99-100 °C(Solv: ligroine (8032-32-4))
• 沸点：
  278.1±40.0 °C(Predicted)
• 密度：
  0.93±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.79
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,4-bis(trimethylsilyl)-2,5-dimethoxybenzene 在 3,3-二甲基-1-(三氟甲基)-1,2-苯并碘氧杂戊环 、 一氯化碘 作用下， 生成 1,4-ditrifluoromethyl-2,5-diiodo-3,6-dimethoxybenzene
  参考文献：
  名称：

  [EN] HIGH-AND LOW-POTENTIAL, WATER-SOLUBLE, ROBUST QUINONES
  [FR] QUINONES ROBUSTES SOLUBLES DANS L'EAU À POTENTIEL FAIBLE ET ÉLEVÉ

  摘要：

  本文披露了取代的对苯二酚、1,4-喹啉醌、邻苯二酚、1,2-喹啉醌、蒽醌和蒽氢醌。取代的对苯二酚和邻苯二酚的化学式为：而取代的1,4-喹啉醌或1,2-喹啉醌具有相应的氧化结构（1,4-苯醌和1,2-苯醌）。R1、R2、R3和R4中的一个或多个包括磺酸酯基、磺酰胺基或膦酸酯基，而不包括这些基团之一的R1、R2、R3和R4包括烷基、环烷基、硫醚、亚硫醚、砜、卤代烷基、卤素、腈、酰亚胺、吡唑或其组合。取代的蒽醌的化学式为：而取代的蒽氢醌具有相应的还原结构。R1-R8中的一个或多个通过硫醚、胺或醚与环相连，包括一个或多个烷基。不含这些基团之一的R1-R8包括烷基、环烷基、硫醚、亚硫醚、砜、卤代烷基、卤素、羟基、烷氧基、醚、胺或氢的任何基团。取代的对苯二酚、1,4-喹啉醌、邻苯二酚、1,2-喹啉醌、蒽醌或蒽氢醌在水中溶解，在水酸性溶液中稳定，并且在氧化形式中具有有用的还原电位。因此，它们可以用作新兴技术中的氧化还原中介体，例如在介导燃料电池或有机介质流动电池中。

  公开号：

  WO2018160618A1
• 作为产物：
  描述：

  对苯二甲醚 在 正丁基锂 、 四甲基乙二胺 作用下， 反应 96.0h， 生成 1,4-bis(trimethylsilyl)-2,5-dimethoxybenzene
  参考文献：
  名称：

  Dilithiation of aromatic ethers

  摘要：

  DOI：

  10.1021/jo00198a015

文献信息

• 1,4-Bis(trimethylsilyl)-2,5-dimethoxybenzene: a novel redox shuttle additive for overcharge protection in lithium-ion batteries that doubles as a mechanistic chemical probe
  作者：Jinhua Huang、Ilya A. Shkrob、Peiqi Wang、Lei Cheng、Baofei Pan、Meinan He、Chen Liao、Zhengcheng Zhang、Larry A. Curtiss、Lu Zhang

  DOI：10.1039/c5ta00899a

  日期：——

  A novel redox shuttle additive, 1,4-bis(trimethylsilyl)-2,5-dimethoxybenzene, is shown to deliver superb overcharge protection of LiFePO₄ electrode in Li-ion batteries.

  一种新型的氧化还原穿梭剂添加剂，1,4-双(三甲基硅基)-2,5-二甲氧基苯，被证明能够在锂离子电池中为LiFePO₄电极提供出色的过充保护。
• A predicative model for certain directed metalations, IV; The dynamic behavior of the organolithio intermediates formed by metalation of p-dimethoxybenzene (p-DMB)
  作者：D.W. Slocum、G. Hayes、N. Kline

  DOI：10.1016/0040-4039(95)01765-a

  日期：1995.11

  Significant disproportionation between the mono- and 2,5-bis-metalaled intermediates resulting from metalation of p-DMB has been observed. The best procedure for the generation of each of these intermediates involves use of an “incremental” amount of TMEDA.1

  已经观察到由p-DMB金属化导致的单金属和2，5-双金属化中间体之间的显着歧化。生成每种中间体的最佳方法是使用“增量”量的TMEDA。1个
• Synthesis of the Tetracyclic Carbon Core of Menogaril Utilizing the Benzannulation Reaction of a Fischer Carbene Complex and an Alkyne
  作者：Jing Su、William D. Wulff、Richard G. Ball

  DOI：10.1021/jo981481w

  日期：1998.11.1

  The synthesis of the 2-bromoanthracyclinone 3 containing the tetracyclic core of menogaril is achieved with a strategy that is formulated around the benzannulation reaction of a Fischer carbene complex and an alkyne. This benzannulation requires a 2,5-dimethoxyphenyl carbene complex that bears an additional functional group at the 4-position that is the nascent 2-bromo substituent in 3. The evaluation of 4-bromo- and 4-trimethysilyl-substituted complexes with 1-pentyne revealed that the benzannulation was more efficient with the silyl complex. The synthesis of 3 is achieved with methoxy and acetoxy substituents at the C-9 position, which begins with the methoxy- and benzyloxy-substituted alkynes 14 and 30 that contain the A ring of the menogaril core. The closure of the last ring is accomplished by a Friedel-Crafts reaction on an in situ generated acid chloride. Adjustment of the oxidation states of the B and C rings failed according to procedures that had been developed in model studies. This was accomplished in an unexpected fashion with novel bromination reactions that occurred at a benzylic position with the C-9 methoxyl derivative and alpha to a ketone in the C-9 acetoxy derivative.
• CROWTHER, G. P.;SUNDBERG, R. J.;SARPESHKAR, ASHOK, M., J. ORG. CHEM., 1984, 49, N 24, 4657-4663
  作者：CROWTHER, G. P.、SUNDBERG, R. J.、SARPESHKAR, ASHOK, M.

  DOI：——

  日期：——
• [EN] HIGH-AND LOW-POTENTIAL, WATER-SOLUBLE, ROBUST QUINONES<br/>[FR] QUINONES ROBUSTES SOLUBLES DANS L'EAU À POTENTIEL FAIBLE ET ÉLEVÉ
  申请人：WISCONSIN ALUMNI RES FOUND

  公开号：WO2018160618A1

  公开（公告）日：2018-09-07

  Substituted hydroquinones, 1,4-quinones, catechols, 1,2-quinones, anthraquinones, and anthrahydroquinones are disclosed herein. The substituted hydroquinones and catechols have the formula: while the substituted 1,4-quinones or 1,2-have the corresponding oxidized structure (1,4- benzoquinones and 1,2-benzoquinones). One or more of R1, R2, R3 and R4 include a sulfonate moiety, a sulfonimide moiety, or a phosphonate moiety, and any of R1, R2, R3 and R4 that do not include one of these moieties include an alkyl, a cycloalkyl, a thioether, a sulfoxide, a sulfone, a haloalkyl, a halogen, a nitrile, an imide, a pyrazole, or combinations thereof. The substituted anthraquinones have the formula: while the substituted anthrahydroquinones have the corresponding reduced structure. One or more of R1-R8 have a sulfonate or phosphate tethered to the ring by a thi other, amine, or ether including one or more alkyl groups. Any of R1-R8 that do not contain one of these moieties include an alkyl, a cycloalkyl, a thiother, a sulfoxide, a sulfone, a haloalkyl, a halogen, a hydroxyl, an alkoxyl, an ether, an amine, or hydrogen The substituted hydroquinones, 1,4-quinones, catechols, 1,2-quinones, anthraquinones, or anthrahydroquinones are soluble in water, stable in aqueous acid solutions, and have useful reduction potentials in the oxidized form. Accordingly, they can be used as redox mediators in emerging technologies, such as in mediated fuel cells or organic-mediator flow batteries.

  本文披露了取代的对苯二酚、1,4-喹啉醌、邻苯二酚、1,2-喹啉醌、蒽醌和蒽氢醌。取代的对苯二酚和邻苯二酚的化学式为：而取代的1,4-喹啉醌或1,2-喹啉醌具有相应的氧化结构（1,4-苯醌和1,2-苯醌）。R1、R2、R3和R4中的一个或多个包括磺酸酯基、磺酰胺基或膦酸酯基，而不包括这些基团之一的R1、R2、R3和R4包括烷基、环烷基、硫醚、亚硫醚、砜、卤代烷基、卤素、腈、酰亚胺、吡唑或其组合。取代的蒽醌的化学式为：而取代的蒽氢醌具有相应的还原结构。R1-R8中的一个或多个通过硫醚、胺或醚与环相连，包括一个或多个烷基。不含这些基团之一的R1-R8包括烷基、环烷基、硫醚、亚硫醚、砜、卤代烷基、卤素、羟基、烷氧基、醚、胺或氢的任何基团。取代的对苯二酚、1,4-喹啉醌、邻苯二酚、1,2-喹啉醌、蒽醌或蒽氢醌在水中溶解，在水酸性溶液中稳定，并且在氧化形式中具有有用的还原电位。因此，它们可以用作新兴技术中的氧化还原中介体，例如在介导燃料电池或有机介质流动电池中。