1,2-dibromo-4,5-bis(tert-butyldimethylsilyloxy)benzene | 914300-26-8

• 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: 1,2-dibromo-4,5-bis(tert-butyldimethylsilyloxy)benzene
• 英文别名: Tert-butyl-[4,5-dibromo-2-[tert-butyl(dimethyl)silyl]oxyphenoxy]-dimethylsilane
• CAS: 914300-26-8
• 化学式: C₁₈H₃₂Br₂O₂Si₂
• 分子量: 496.43
• InChiKey: AKDJOZHOOFHDMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.98
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  1,2-dibromo-4,5-bis(tert-butyldimethylsilyloxy)benzene 在 potassium fluoride 、 正丁基锂 、 dibromo[1,2-bis(diphenylphosphino)ethane]nickel(II) 、 锌 作用下， 以 四氢呋喃 、 正己烷 、 乙腈 为溶剂， 反应 27.0h， 生成 3,4-dihydroxy-7,8-dimethoxy-6H-naphtho[1,2-b]benzo[d]pyran-6-one
  参考文献：
  名称：

  Nickel-Catalyzed Synthesis of Benzocoumarins:  Application to the Total Synthesis of Arnottin I

  摘要：

  The ring-opening addition of methyl 2,3-dimethoxy-6-iodobenzoate to oxabenzonorbornadienes followed by cyclization in the presence of NiBr2( dppe) and Zn metal powder in acetonitrile at 80 C to give the corresponding benzocoumarin derivatives is described. This methodology was then applied to the synthesis of natural product arnottin I, first isolated from Xanthoxylum arnottianum Maxim, using protecting group chemistry. After deprotection and subsequent ring closure, arnottin I was obtained in 21% overall yield after six steps starting from catechol.

  DOI：

  10.1021/jo061477h
• 作为产物：
  描述：

  4,5-二溴-1,2-二甲氧基苯 、 叔丁基二甲基氯硅烷 在 三溴化硼 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 以99%的产率得到1,2-dibromo-4,5-bis(tert-butyldimethylsilyloxy)benzene
  参考文献：
  名称：

  Rational synthesis of bis(hexyloxy)-tetra(hydroxy)-triphenylenes and their derivatives

  摘要：

  描述了三种新的四(羟基)-三苯基衍生物的合成及其作为合理设计的混合取代基三苯基衍生物平台的应用。

  DOI：

  10.1039/c4ra06503d

文献信息

• Facile Cyclization of Terphenyl to Triphenylene: A New Chemodosimeter for Fluoride Ions
  作者：Vandana Bhalla、Hardev Singh、Manoj Kumar

  DOI：10.1021/ol902861b

  日期：2010.2.5

  Terphenyl derivatives 3 and 4 having OTBS groups have been synthesized via a Suzuki-Miyura coupling reaction, These compounds undergo unprecedented irreversible cyclization to symmetrically/unsymmetrically substituted triphenylenes while carrying out the deprotection of OTBS groups using tetrabutylammonium fluoride. Terphenyl 3 also serves as a new chemodosimeter for fluoride ions.
• Terphenyl based ‘Turn On’ fluorescent sensor for mercury
  作者：Vandana Bhalla、Ruchi Tejpal、Manoj Kumar、Rajiv Kumar Puri、Rakesh K. Mahajan

  DOI：10.1016/j.tetlet.2009.03.110

  日期：2009.6

  New terphenyl-based derivative 4 with pyrene as a fluorophore has been synthesized and examined for its cation recognition abilities toward various cations by NMR and fluorescence spectroscopy. The results show that it has very high binding affinity (log beta = 5.12) and selectivity for mercury. A fluorescence enhancement of 375% was observed for the 4-Hg2+ system in THF. A Hg2+ selective electrode (ISE) was also formed which showed excellent selectivity over all the Other cations rested. The lower limit of detection is 2.1 x 10(-6) M. (C) 2009 Elsevier Ltd. All rights reserved.
• Nickel-Catalyzed Synthesis of Benzocoumarins:  Application to the Total Synthesis of Arnottin I
  作者：Sachin Madan、Chien-Hong Cheng

  DOI：10.1021/jo061477h

  日期：2006.10.1

  The ring-opening addition of methyl 2,3-dimethoxy-6-iodobenzoate to oxabenzonorbornadienes followed by cyclization in the presence of NiBr2( dppe) and Zn metal powder in acetonitrile at 80 C to give the corresponding benzocoumarin derivatives is described. This methodology was then applied to the synthesis of natural product arnottin I, first isolated from Xanthoxylum arnottianum Maxim, using protecting group chemistry. After deprotection and subsequent ring closure, arnottin I was obtained in 21% overall yield after six steps starting from catechol.
• Rational synthesis of bis(hexyloxy)-tetra(hydroxy)-triphenylenes and their derivatives
  作者：Merry K. Smith、Natalia E. Powers-Riggs、Brian H. Northrop

  DOI：10.1039/c4ra06503d

  日期：——

  The synthesis of three new tetra(hydroxy)-triphenylene derivatives and their use as platforms for rationally designed, mixed-substituent triphenylene derivatives is described.

  描述了三种新的四(羟基)-三苯基衍生物的合成及其作为合理设计的混合取代基三苯基衍生物平台的应用。