7-(tert-butyldimethyl)silyloxy-7-methoxy-bicyclo[4.2.0]octa-1,3,5-triene | 1437769-78-2

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 7-(tert-butyldimethyl)silyloxy-7-methoxy-bicyclo[4.2.0]octa-1,3,5-triene
• 英文别名: 1-(tert-butyldimethylsilyloxy)-1-methoxy-1,2-dihydrobenzocyclobutene；Tert-butyl-[(7-methoxy-7-bicyclo[4.2.0]octa-1,3,5-trienyl)oxy]-dimethylsilane；tert-butyl-[(7-methoxy-7-bicyclo[4.2.0]octa-1,3,5-trienyl)oxy]-dimethylsilane
• CAS: 1437769-78-2
• 化学式: C₁₅H₂₄O₂Si
• 分子量: 264.44
• InChiKey: OVIKRKNDQABCEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.06
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(4,4,5,5-四甲基-1,3,2-二杂氧戊硼烷-2-基)苯酚 在 仲丁基锂 、 N,N-二异丙基乙胺 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 、 环己烷 为溶剂， 反应 3.5h， 生成 7-(tert-butyldimethyl)silyloxy-7-methoxy-bicyclo[4.2.0]octa-1,3,5-triene
  参考文献：
  名称：

  Generation of Arynes via Ate Complexes of Arylboronic Esters with an ortho-Leaving Group

  摘要：

  An efficient method of generating aryne has been achieved by treating ortho-(trifluoromethanesulfonyloxy)arylboronic acid pinacol ester with tert-or sec-butyllithium. Monitoring the reaction by B-11 NMR has indicated that a boron-ate complex formed in situ is the eventual precursor that converts into aryne near room temperature. The prior formation of the ate complex at a low temperature has enabled us to use various arynophiles, including those bearing base-sensitive groups. The ready availability of the aryne precursors and mutual orthogonality in aryne generation with widely used ortho-silylaryl triflate have enhanced the utility of the method.

  DOI：

  10.1021/ol401140d

文献信息

• Generation of Arynes by Selective Cleavage of a Carbon–Phosphorus Bond of <i>o</i>-(Diarylphosphinyl)aryl Triflates Using a Grignard Reagent
  作者：Yoshitake Nishiyama、Shuhei Kamada、Suguru Yoshida、Takamitsu Hosoya

  DOI：10.1246/cl.180555

  日期：2018.9.5

  A novel method for generating arynes, including disubstituted benzynes and a dehydrophenoxathiin, is reported. The treatment of easily synthesizable o-(diarylphosphinyl)aryl triflates having two el...

  报道了一种用于生成芳烃的新方法，包括双取代苄和脱氢吩恶噻英。易于合成的邻（二芳基膦基）芳基三氟甲磺酸酯的处理，具有两个...
• Generation of Arynes Using Trimethylsilylmethyl Grignard Reagent for Activation of <i>ortho</i>-Iodoaryl or <i>ortho</i>-Sulfinylaryl Triflates
  作者：Suguru Yoshida、Keisuke Uchida、Takamitsu Hosoya

  DOI：10.1246/cl.150060

  日期：2015.5.5

  The trimethylsilylmethyl Grignard reagent triggered efficient generation of arynes from various ortho-iodoaryl or ortho-sulfinylaryl triflates. The moderate nucleophilicity and basicity of the reagent facilitated efficient reactions between the aryne precursors and arynophiles containing organometallic nucleophile-sensitive functionalities.

  三甲基硅甲基格氏试剂触发了多种邻碘芳基或邻亚砜芳基三氟甲磺酸酯生成氮烯的高效过程。该试剂适度的亲核性和碱性促进了氮烯前体与含金属有机亲核敏感功能的氮烯受体之间的高效反应。
• Generation of Arynes via Ate Complexes of Arylboronic Esters with an <i>ortho</i>-Leaving Group
  作者：Yuto Sumida、Tomoe Kato、Takamitsu Hosoya

  DOI：10.1021/ol401140d

  日期：2013.6.7

  An efficient method of generating aryne has been achieved by treating ortho-(trifluoromethanesulfonyloxy)arylboronic acid pinacol ester with tert-or sec-butyllithium. Monitoring the reaction by B-11 NMR has indicated that a boron-ate complex formed in situ is the eventual precursor that converts into aryne near room temperature. The prior formation of the ate complex at a low temperature has enabled us to use various arynophiles, including those bearing base-sensitive groups. The ready availability of the aryne precursors and mutual orthogonality in aryne generation with widely used ortho-silylaryl triflate have enhanced the utility of the method.