2-[(2-甲基丙烷-2-基)氧基]乙基苯 | 3354-66-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-[(2-甲基丙烷-2-基)氧基]乙基苯
• 英文名称: tert-butyl 2-phenylethyl ether
• 英文别名: (2-tert-butoxy-ethyl)-benzene；Ph-CH2CH2OCMe3；2-[(1,1-dimethylethyl)oxy]ethyl-benzene；2-Phenylethyl tert-butyl ether；2-[(2-methylpropan-2-yl)oxy]ethylbenzene
• CAS: 3354-66-3
• 化学式: C₁₂H₁₈O
• 分子量: 178.274
• InChiKey: UPKHTMNSMRJUHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2909309090

反应信息

• 作为反应物：
  描述：

  2-[(2-甲基丙烷-2-基)氧基]乙基苯 在 二氧化氮 、 臭氧 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 3-nitrophenethyl tert-butyl ether 、 1-(2-tert-Butoxy-ethyl)-4-nitro-benzene 、 1-(2-tert-Butoxy-ethyl)-2-nitro-benzene
  参考文献：
  名称：

  Ozone-Mediated Nitration of Phenylalkyl Ethers, Phenylacetic Esters, and Related Compounds with Nitrogen Dioxide. The Highest Ortho Substitution Observed in the Electrophilic Nitration of Arenes

  摘要：

  Ey the combined action of ozonized oxygen and nitrogen dioxide (the kyodai-nitration), the title compounds were smoothly nitrated in dichloromethane at subzero degrees with high ortho positional selectivity. Although the conventional nitration of phenylacetic acid and esters mainly produces m- and p-nitro derivatives, the present nitration offers a simple high-yield synthesis of o-nitro derivatives which are important as precursor in organic synthesis, The proportions of the ortho isomer in the nitration products from methyl 2-phenylethyl ether and methyl phenylacetate were 71 and 88%, respectively, the latter value being the highest ortho isomer proportion so far observed in the electrophilic aromatic nitration. The observed high ortho selectivity has been rationalized in terms of radical cation intermediate and six-membered cyclic transition state.

  DOI：

  10.1021/jo9606867
• 作为产物：
  描述：

  [2-(Benzenesulfonyl)-2-[(2-methylpropan-2-yl)oxy]ethyl]benzene 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以100%的产率得到2-[(2-甲基丙烷-2-基)氧基]乙基苯
  参考文献：
  名称：

  Julia, Marc; Uguen, Daniel; Zhang, Da, Australian Journal of Chemistry, 1995, vol. 48, # 2, p. 279 - 290

  摘要：

  DOI：

文献信息

• Saccharin sulfonic acid catalyzed N-Boc protection of amines and formation of tert-butyl ethers from alcohols
  作者：F. Shirini、M. A. Zolfigol、M. Abedini

  DOI：10.1007/bf03246047

  日期：2010.9

  (SaSA), as a stable reagent is easily prepared by the reaction of saccharin with neat chlorosulfonic acid at room temperature. This compound is able to catalyze conversion of amines to their corresponding N-Boc protected amines with (Boc)2O. Alcohols were also converted to their corresponding tert-butyl ethers. All reactions took place under mild conditions giving the desired products in good to high

  通过在室温下使糖精与纯净的氯磺酸反应，可以容易地制备作为稳定试剂的糖精磺酸（SaSA）。该化合物能够用（Boc）2 O催化胺转化为其相应的N- Boc保护的胺。醇也被转化为其相应的叔丁基醚。所有反应均在温和条件下进行，以高至高收率得到所需产物。
• Gold(I)-Catalyzed Synthesis of Unsymmetrical Ethers Using Alcohols as Alkylating Reagents
  作者：Yongxiang Liu、Xiaoyu Wang、Yanshi Wang、Chuan Du、Hui Shi、Shengfei Jin、Chongguo Jiang、Jianyong Xiao、Maosheng Cheng

  DOI：10.1002/adsc.201401097

  日期：2015.3.23

  microwave‐irradiated alcohol‐protecting strategy based on gold catalysis utilizing benzyl alcohol, tert‐butyl alcohol and triphenylmethanol as alkylating reagents has been developed. This protecting strategy has wide functional group tolerance with satisfactory yields for the majority of the selected alcohols. The mechanism of this transformation was probed with oxygen‐18 isotope labelled alcohols assisted by

  基于苄基醇，叔丁醇和三苯甲醇作为烷基化试剂的金催化的微波辐射醇保护策略已经被开发出来。对于大多数选定的醇，该保护策略具有宽泛的官能团耐受性和令人满意的产率。在GC-MS技术和化学动力学实验的辅助下，用氧18同位素标记的醇探索了这种转变的机理。该策略为有机合成中的苄基，叔丁基和三苯甲基醚的制备提供了一种有效，直接和替代的方法。
• Zeolites Catalyze the Nazarov Reaction and the tert-Butylation of Alcohols by Stabilization of Carboxonium Intermediates
  作者：Antonio Leyva-Pérez、María Tejeda-Serrano、Sergio Sanz-Navarro、Finn Blake

  DOI：10.1055/s-0039-1690896

  日期：2020.7

  Zeolites are the most used catalysts worldwide in petrochemistry processes, with particular ability to stabilize carbocations. However, the use of zeolites in organic synthesis is still scarce. We show here that representative carboxonium-mediated organic reactions, such as the Nazarov cyclization and the tert-butylation of alcohols with tert-butyl acetate, typically performed with very strong acid

  沸石是全球范围内石化工艺中最常用的催化剂，具有稳定碳正离子的特殊能力。然而，在有机合成中仍很少使用沸石。我们在这里展示的是代表carboxonium介导的有机反应，如环化纳扎罗夫和叔醇与-butylation叔丁基乙酸酯，典型地在溶液中非常强的酸催化剂如三氟甲磺酸进行的，可以通过用简单的沸石催化高收率和选择性。铝硅酸盐骨架稳定了中间的碳氢化合物种类，并超越了溶液中对超酸质子的需求。
• Suzuki Coupling of Potassium Cyclopropyl- and Alkoxymethyltrifluoroborates with Benzyl Chlorides
  作者：Virginie Colombel、Frederik Rombouts、Daniel Oehlrich、Gary A. Molander

  DOI：10.1021/jo202686p

  日期：2012.3.16

  Efficient Csp3–Csp3 Suzuki couplings have been developed with both potassium cyclopropyl- and alkoxymethyltrifluoroborates. Moderate to good yields have been achieved in the cross-coupling of potassium cyclopropyltrifluoroborate with benzyl chlorides possessing electron-donating or electron-withdrawing substituents. Benzyl chloride was also successfully cross-coupled to potassium alkoxymethyltrifluoroborates

  使用环丙基三氟硼酸钾和烷氧基甲基三氟硼酸钾开发了高效的 Csp 3 –Csp 3 Suzuki 偶联物。在环丙基三氟硼酸钾与具有给电子或吸电子取代基的苄基氯的交叉偶联中，已经实现了中等至良好的产率。苄基氯还成功地与衍生自伯醇、仲醇和叔醇的烷氧基甲基三氟硼酸钾交叉偶联。
• 一种含碳-硅键化合物及其应用
  申请人：中国科学院上海有机化学研究所

  公开号：CN111592563A

  公开（公告）日：2020-08-28

  本发明公开了一种含碳‑硅键化合物及其在构建碳‑碳键中的应用。本发明提供了一种如式I或式I’所示的含碳‑硅键化合物在构建碳‑碳键的化学反应中的应用；所述的碳‑碳键中的一个碳来自于所述的含碳‑硅键化合物中与硅连接的碳。本发明提供的制备方法，使用含碳‑硅键化合物提供碳自由基，能在温和条件下与另一分子中提供的碳直接反应，构建碳‑碳键；该制备方法底物适用范围更广，不仅适用于官能团活化的C和碳自由基底物，还可适用于未活化的C‑H键底物。