1-Trimethylsilanyloxy-4-(1-trimethylsilanyloxy-vinyl)-benzene | 60068-18-0

• 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-Trimethylsilanyloxy-4-(1-trimethylsilanyloxy-vinyl)-benzene
• 英文别名: 1-(1-Trimethylsiloxyethenyl)-4-trimethylsiloxy-benzene；trimethyl-[4-(1-trimethylsilyloxyethenyl)phenoxy]silane
• CAS: 60068-18-0
• 化学式: C₁₄H₂₄O₂Si₂
• 分子量: 280.514
• InChiKey: QQEJBUVWRWDTEJ-UHFFFAOYSA-N

物化性质

• 沸点：
  281.8±23.0 °C(Predicted)
• 密度：
  0.925±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.72
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 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-Trimethylsilanyloxy-4-(1-trimethylsilanyloxy-vinyl)-benzene 、 5-苯基呋喃-2,3-二酮 以 甲苯 为溶剂， 反应 1.0h， 以37%的产率得到2-(4-羟基苯基)-6-苯基吡喃-4-酮
  参考文献：
  名称：

  Thermal Cycloaddition of Aroylketene to 1-Aryl-1-trimethylsilyloxyethylene: A Simple Synthesis of 2,6-Diaryl-4H-pyran-4-one

  摘要：

  Aroylketene (2) generated by pyrolytic decarbonylation of 5-aryl-2,3-dihydro-2,3-furandione (1) reacted with 1-aryl-1-trimethylsilyloxyethylene (3) in a regioselective manner to give 2,6-diaryl-4H-pyran-4-one (5) and/or 1,5-diarylpentane-1,3,5-trione (6). This reaction provides a simple synthetic method of 2,6-diaryl-4H-pyran-4-one with various substituents in the aryl group.

  DOI：

  10.3987/com-93-6434
• 作为产物：
  描述：

  三甲基氯硅烷 、 对羟基苯乙酮 在 三乙胺 、 sodium iodide 作用下， 以 乙腈 为溶剂， 生成 1-Trimethylsilanyloxy-4-(1-trimethylsilanyloxy-vinyl)-benzene
  参考文献：
  名称：

  使用二芳基碘鎓盐的多功能无碱铜催化芳香酮的α-芳基化

  摘要：

  描述了一种用于芳香酮有效α-芳基化的配体和无碱铜催化合成方法。为了避免强碱，使用了酮衍生的甲硅烷基烯醇醚。它们与作为芳基源的二芳基碘盐的反应提供了分子间 C-C 偶联，显示出良好的官能团耐受性并且需要低催化剂负载。

  DOI：

  10.1016/j.tetlet.2021.153208

文献信息

• Phenolic compounds from roots of Urtica dioica
  作者：Rupert Kraus、Gerhard Spiteller

  DOI：10.1016/0031-9422(90)80140-c

  日期：1990.1

  Abstract Root extracts from Urtica dioica were separated into several classes of compounds by extraction with organic solvents at different pH values. The phenolic fraction was analysed by GC-MS after trimethylsilylation. This procedure allowed the identification of 18 phenolic compounds as well as the detection of eight lignans. The occurrence of some of these substances in this plant was previously

  摘要 通过用不同pH 值的有机溶剂提取，荨麻根提取物被分离成几类化合物。在三甲基甲硅烷基化后通过 GC-MS 分析酚级分。该程序允许识别 18 种酚类化合物以及检测 8 种木脂素。这些物质中的一些在这种植物中的存在以前是未知的。
• Thermal Addition Reaction of Aroylketene with 1-Aryl-1-trimethylsilyloxyethylenes: Aromatic Substituent Effects of Aroylketene and Aryltrimethylsilyloxyethylene on Their Reactivity.
  作者：Toshiaki SAITOH、Taichi OYAMA、Kiyomi SAKURAI、Yosihiro NIIMURA、Mitsuru HINATA、Yoshie HORIGUCHI、Jun TODA、Takehiro SANO

  DOI：10.1248/cpb.44.956

  日期：——

  The thermal addition reaction of various aroylketenes (C) generated by the thermolysis of 5-aryldioxofurans (A) to 1-aryl-1-trimethylsilyloxyethylenes gave 1, 5-diarylpentane-1, 3, 5-triones (D) and 2, 6-diaryl-4H-pyran-4-ones (E). The introduction of electron withdrawing substituents in the aroylketene and of electron donating substituents facilitated the addition reaction. The observed substituent effects and the reaction mechanism are interpreted in terms of molecular orbital analyses.

  通过对5-芳基二氧呋喃（A）的热分解生成的多种芳酰基酮（C）与1-芳基-1-三甲基硅氧基乙烯的热加成反应，生成了1, 5-二芳基戊烷-1, 3, 5-三酮（D）和2, 6-二芳基-4H-吡喃-4-酮（E）。在芳酰基酮中引入电子拉电子取代基以及在反应中引入电子给体取代基促进了加成反应。观察到的取代基效应和反应机制通过分子轨道分析进行了解释。
• Design, synthesis, and evaluation of curcumin-derived arylheptanoids for glioblastoma and neuroblastoma cytotoxicity
  作者：Catherine A. Campos、Joseph B. Gianino、Barbara J. Bailey、Mary E. Baluyut、Constanze Wiek、Helmut Hanenberg、Harlan E. Shannon、Karen E. Pollok、Brandon L. Ashfeld

  DOI：10.1016/j.bmcl.2013.09.095

  日期：2013.12

  Using an innovative approach toward multiple carbon-carbon bond-formations that relies on the multifaceted catalytic properties of titanocene complexes we constructed a series of C1-C7 analogs of curcumin for evaluation as brain and peripheral nervous system anti-cancer agents. C2-Arylated analogs proved efficacious against neuroblastoma (SK-N-SH & SK-N-FI) and glioblastoma multiforme (U87MG) cell lines. Similar inhibitory activity was also evident in p53 knockdown U87MG GBM cells. Furthermore, lead compounds showed limited growth inhibition in vitro against normal primary human CD34+ hematopoietic progenitor cells. Taken together, the present findings indicate that these curcumin analogs are viable lead compounds for the development of new central and peripheral nervous system cancer chemotherapeutics with the potential for little effects on normal hematopoietic progenitor cells. (C) 2013 Elsevier Ltd. All rights reserved.
• van der Vecht,J.R. et al., Recueil des Travaux Chimiques des Pays-Bas, 1976, vol. 95, p. 149 - 152
  作者：van der Vecht,J.R. et al.

  DOI：——

  日期：——
• Unusual fragmentation of trimethylsilylated enols derived fromm- andp-hydroxyacetophenones
  作者：Rupert Kraus、Gerhard Spiteller

  DOI：10.1002/oms.1210241002

  日期：1989.10

  AbstractWhen 4‐hydroxyacetophenone is treated with MSTFA the corresponding bis‐trimethylsilylated enol ether (1a) is obtained. The mass spectrum of la is characterized by a [M – 1]+ base peak. Extensive deuteration experiments revealed that the hydrogen is mainly removed from a ring position, but originates also to some extent from the side chain (methylidene group) and even to a very small amount from the hydrogens of the methyl groups of the enolic trimethylsilyl group. A mechanism for this fragmentation behaviour is formulated.