tert-butyl(3-(tert-butyl)phenoxy)dimethylsilane | 1254941-68-8

• 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: tert-butyl(3-(tert-butyl)phenoxy)dimethylsilane
• 英文别名: tert-butyldimethylsilyloxy-3-tert-butylbenzene；Tert-butyl-(3-tert-butylphenoxy)-dimethylsilane；tert-butyl-(3-tert-butylphenoxy)-dimethylsilane
• CAS: 1254941-68-8
• 化学式: C₁₆H₂₈OSi
• 分子量: 264.483
• InChiKey: ZGTYFSHFSYUOLG-UHFFFAOYSA-N

物化性质

• 沸点：
  284.2±19.0 °C(Predicted)
• 密度：
  0.886±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.37
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  tert-butyl(3-(tert-butyl)phenoxy)dimethylsilane 在 2-双环己基膦-2',6'-二甲氧基联苯 、 potassium phosphate 、 (1,5-cyclooctadiene)(methoxy)iridium(I) dimer 、 palladium diacetate 、 4,4'-二叔丁基-2,2'-二吡啶 作用下， 以 四氢呋喃 、 环己烷 、 水 为溶剂， 反应 24.0h， 生成 ((5,5''-di-tert-butyl-[1,1':3',1''-terphenyl]-3,3''-diyl)bis(oxy))bis(tert-butyldimethylsilane)
  参考文献：
  名称：

  Synthesis of Hyperbranched Poly(m-phenylene)s via Suzuki Polycondensation of a Branched AB₂ Monomer

  摘要：

  An efficient synthesis of hyperbranched poly(m phenylene)s is achieved by Suzuki poly condensation of a m-terphenyl derived branched AB(2) monomer The resulting hyperbranched polymers show high molecular weight and relatively low polydispersity and are readily soluble in common organic solvents A catalyst system composed of Pd(OAc)(2) and S Phos was found to be highly active in the present Suzuki polycondensation protocol The molecular weight and polydispersity of the polymer are controllable by varying the catalyst loading and the starting monomer concentration Experimental results are consistent with a pseudo-chain-growth pathway that Involves intramolecular catalyst transfer during polymerization Furthermore, the triflate end groups of the hyperbranched poly(m phenylene)s can be efficiently converted to other functionalities via in situ Suzuki-Miyaura cross-couplings

  DOI：

  10.1021/ma102023a
• 作为产物：
  描述：

  3-叔丁基苯酚 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以99%的产率得到tert-butyl(3-(tert-butyl)phenoxy)dimethylsilane
  参考文献：
  名称：

  Synthesis of Hyperbranched Poly(m-phenylene)s via Suzuki Polycondensation of a Branched AB₂ Monomer

  摘要：

  An efficient synthesis of hyperbranched poly(m phenylene)s is achieved by Suzuki poly condensation of a m-terphenyl derived branched AB(2) monomer The resulting hyperbranched polymers show high molecular weight and relatively low polydispersity and are readily soluble in common organic solvents A catalyst system composed of Pd(OAc)(2) and S Phos was found to be highly active in the present Suzuki polycondensation protocol The molecular weight and polydispersity of the polymer are controllable by varying the catalyst loading and the starting monomer concentration Experimental results are consistent with a pseudo-chain-growth pathway that Involves intramolecular catalyst transfer during polymerization Furthermore, the triflate end groups of the hyperbranched poly(m phenylene)s can be efficiently converted to other functionalities via in situ Suzuki-Miyaura cross-couplings

  DOI：

  10.1021/ma102023a

文献信息

• Catalytic Transfer Hydrogenation of Arenes and Heteroarenes
  作者：Coralie Gelis、Arne Heusler、Zackaria Nairoukh、Frank Glorius

  DOI：10.1002/chem.202002777

  日期：2020.11.6

  Transfer hydrogenation reactions are of great interest to reduce diverse molecules under mild reaction conditions. To date, this type of reaction has only been successfully applied to alkenes, alkynes and polarized unsaturated compounds such as ketones, imines, pyridines, etc. The reduction of benzene derivatives by transfer hydrogenation has never been described, which is likely due to the high energy

  转移氢化反应对于在温和的反应条件下还原各种分子非常重要。迄今为止，这种类型的反应仅成功地用于烯烃，炔烃和极化的不饱和化合物，例如酮，亚胺，吡啶等。从未描述过通过转移氢化还原苯衍生物的方法，这很可能是由于高使这些化合物脱芳香化所需的能量屏障。在此背景下，我们开发了一种催化转移氢化反应，用于还原苯衍生物和杂芳烃，从而在不需要压缩氢气的情况下，在室温下形成带有各种官能团的复杂三维支架。
• Nickel-Catalyzed Kumada Cross-Coupling Reactions of Tertiary Alkylmagnesium Halides and Aryl Bromides/Triflates
  作者：Amruta Joshi-Pangu、Chao-Yuan Wang、Mark R. Biscoe

  DOI：10.1021/ja202769t

  日期：2011.6.8

  We report a Ni-catalyzed process for the cross-coupling of tertiary alkyl nucleophiles and aryl bromides. This process is extremely general for a wide range of electrophiles and generally occurs with a ratio of retention to isomerization >30:1. The same procedure also accommodates the use of aryl triflates, vinyl chlorides, and vinyl bromides as the electrophilic component.

  我们报告了一种用于叔烷基亲核试剂和芳基溴化物交叉偶联的 Ni 催化过程。这个过程对于范围广泛的亲电子试剂来说是非常普遍的，并且通常在保留与异构化的比率 > 30:1 的情况下发生。相同的程序也适用于使用芳基三氟甲磺酸酯、氯乙烯和溴乙烯作为亲电子组分。
• Access to “Friedel–Crafts-Restricted” <i>tert</i>-Alkyl Aromatics by Activation/Methylation of Tertiary Benzylic Alcohols
  作者：Joshua A. Hartsel、Derek T. Craft、Qiao-Hong Chen、Ming Ma、Paul R. Carlier

  DOI：10.1021/jo202371c

  日期：2012.4.6

  Herein we describe a two-step protocol to prepare m-tert-alkylbenzenes. The appropriate tertiary benzylic alcohols are activated with SOCl2 or concentrated HCl and then treated with trimethylaluminum, affording the desired products in 68-97% yields (22 examples). This reaction sequence is successful in the presence of a variety of functional groups, including acid-sensitive and Lewis-basic groups. In addition to t-Bu groups, 1,1-dimethylpropyl and 1-ethyl-1-methylpropyl groups can also be installed using this method.
• Synthesis of Hyperbranched Poly(<i>m</i>-phenylene)s via Suzuki Polycondensation of a Branched AB₂ Monomer
  作者：Zheng Xue、Aaron D. Finke、Jeffrey S. Moore

  DOI：10.1021/ma102023a

  日期：2010.11.23

  An efficient synthesis of hyperbranched poly(m phenylene)s is achieved by Suzuki poly condensation of a m-terphenyl derived branched AB(2) monomer The resulting hyperbranched polymers show high molecular weight and relatively low polydispersity and are readily soluble in common organic solvents A catalyst system composed of Pd(OAc)(2) and S Phos was found to be highly active in the present Suzuki polycondensation protocol The molecular weight and polydispersity of the polymer are controllable by varying the catalyst loading and the starting monomer concentration Experimental results are consistent with a pseudo-chain-growth pathway that Involves intramolecular catalyst transfer during polymerization Furthermore, the triflate end groups of the hyperbranched poly(m phenylene)s can be efficiently converted to other functionalities via in situ Suzuki-Miyaura cross-couplings