tert-butyl 3,5-dibromosalicylate | 88797-22-2

• 物质功能分类: 有机原料 - 烃类化合物及其衍生物 - 烃类卤化物
• 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 3,5-dibromosalicylate
• 英文别名: tert-butyl 3,5-dibromosalicylic acid；tert-Butyl 3,5-dibromo-2-hydroxybenzoate
• CAS: 88797-22-2
• 化学式: C₁₁H₁₂Br₂O₃
• 分子量: 352.022
• InChiKey: MFZYAHYEMPWVFL-UHFFFAOYSA-N

物化性质

• 沸点：
  318.7±37.0 °C(Predicted)
• 密度：
  1.694±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl 3,5-dibromosalicylate 在 potassium tert-butylate 、 三氟乙酸 作用下， 反应 1.25h， 生成 trimesoyl tris(3,5-dibromosalicylate)
  参考文献：
  名称：

  Trimesoyltris(3,5-dibromosalicylate): specificity of reactions of a trifunctional acylating agent with hemoglobin

  摘要：

  Trimesoyltris(3,5-dibromosalicylate)(TTDS) was prepared and evaluated as a trifunctional site-directed protein cross-linking reagent. It is synthesized by reaction of trimesoyl chloride with tert-butyl 3,5-dibromosalicylate, followed by deprotection with trifluoroacetic acid. TTDS reacts with the deoxy form of human hemoglobin A and with carbonmonoxyhemoglobin to produce amides from the epsilon-amino groups of Lys-82 of each of the beta chains of hemoglobin. The third 3,5-dibromosalicylate ester group from TTDS reacts much more slowly, principally undergoing hydrolysis. Minor products include materials with alpha-chain modification and triply linked trimesoyl (beta82Lys, beta1Val, beta'82Lys)hemoglobin. Comparison of these results with results from other reagents indicates that the nature of the leaving group and the structure of the acylating core control the observed specificity.

  DOI：

  10.1021/ja00050a005

文献信息

• Synthesis, Conformation and Chiroptical Properties of Diaryl Esters of Tartaric Acid
  作者：Robert Cysewski、Marcin Kwit、Beata Warżajtis、Urszula Rychlewska、Jacek Gawroński

  DOI：10.1021/jo900206c

  日期：2009.6.19

  Previously unknown diaryl esters of l-tartaric acid have been synthesized. Their conformations have been studied by DFT calculations, NMR and circular dichroism spectroscopy in solution, as well as by X-ray diffraction in the crystalline state. The four-carbon tartrate chain of diaryl esters was found to be extended in all cases, with a higher degree of nonplanarity in the crystals. Dinaphthyl tartrates

  先前未知的1-酒石酸二芳基酯已经合成。通过溶液中的DFT计算，NMR和圆二色光谱以及结晶态的X射线衍射研究了它们的构象。发现在所有情况下二芳基酯的四碳酒石酸盐链都被延伸，晶体中的非平面度更高。二萘基酒石酸盐显示异常强大激子棉效应（阿= -228为二-1-萘基升-酒石酸盐），由于允许1B的耦合b之间在萘基中的发色团的转换，尽管无环结构和显著距离（超过10埃）两个生色团。
• An ether-linked tetrafunctional acylating reagent and its cross-linking reactions with hemoglobin
  作者：Ronald Kluger、Krisztina Paal、J Gordon Adamson

  DOI：10.1139/v98-236

  日期：1999.2.1

  A new type of tetrafunctional reagent for cross-linking proteins has been prepared and used to modify human hemoglobin A. DPEE (1,2-bis2-[3,5-bis(3,5-dibromosalicyloxycarbonyl) phenoxy]ethoxy}ethane)) has two separate pairs of reacting sites connected by a flexible tetraether chain. DPEE is capable of connecting a cross-link within a protein to another cross-link, either within the same protein molecule or between molecules. DPEE was readily prepared by esterification of a tetraether-linked bisphthalate (prepared by coupling of 1,2-bis(2-iodoethoxy)ethane and 5-hydroxyisophthalic acid). DPEE reacts with deoxy hemoglobin to produce a mixture of modified proteins. Ion-exchange HPLC was used to separate the modified proteins in the mixture. The most abundant products were selected for structural analysis, which used data from reverse-phase chromatography and tryptic peptide mapping. To prevent dissociation of the modified proteins during analysis, the products were further reacted with the bifunctional reagent, bis(3,5-dibromosalicyl) fumarate, which produces fumaryl cross-links between α-subunits. From peptide analysis of the separated products, the major modified protein from DPEE was identified as a novel species with four links within the same α₂β₂ tetramer. In addition, a minor product that involves cross-links in two different proteins was observed. These results imply that the reagent reacts primarily in a folded state within the protein.Key words: acylation: cross-linking, multifunctional, hemoglobin, reaction pattern.

  一种新型的四官能试剂已制备并用于修饰人类血红蛋白A。DPEE（1,2-双2-[3,5-双（3,5-二溴水杨酰氧基）苯氧基]乙氧基}乙烷）具有由柔性四醚链连接的两个独立的反应位点对。DPEE能够将蛋白质内的交联连接到另一个交联，无论是在同一蛋白质分子中还是在分子之间。DPEE通过酯化四醚连接的双邻苯二甲酸（由1,2-双（2-碘乙氧基）乙烷和5-羟基异苯二甲酸偶联制备）而轻松制备。DPEE与脱氧血红蛋白反应产生一种修改的蛋白质混合物。离子交换高效液相色谱法用于分离混合物中的修改蛋白质。最丰富的产物被选为结构分析的对象，该分析使用反相色谱和胰蛋白酶肽图谱的数据。为了防止分析过程中修改的蛋白质解离，产品进一步与双官能试剂3,5-双溴水杨酸富马酸酯反应，产生α-亚基之间的富马酰交联。从分离的产物的肽分析中，确定了来自DPEE的主要修改蛋白质是一种新物种，它在同一α₂β₂四聚体中具有四个连接。此外，还观察到涉及两种不同蛋白质的交联的次要产物。这些结果表明，该试剂主要在蛋白质内的折叠状态下反应。关键词：酰化、交联、多功能、血红蛋白、反应模式。
• Hemoglobin intramolecularly cross-linked with trivalent reagents
  申请人：The University of Maryland Baltimore

  公开号：US05290919A1

  公开（公告）日：1994-03-01

  Stroma-free hemoglobin cross-linked with reagents that mimic 2,3-diphosphoglycerate and transform stroma-free hemoglobin into a physiologically competent oxygen carrier which is retained in vivo for adequate periods of time, and thus can be used in fluids for transporting oxygen is described.

  本文描述了使用仿制2,3-二磷酸甘油酸的试剂交联无基质血红蛋白，将其转化为生理上具有竞争力的氧载体，并在体内保留足够长时间，因此可用于液体输送氧气。
• Subunit-directed click coupling via doubly cross-linked hemoglobin efficiently produces readily purified functional bis-tetrameric oxygen carriers
  作者：Serena Singh、Ina S. Dubinsky-Davidchik、Ying Yang、Ronald Kluger

  DOI：10.1039/c5ob01755f

  日期：——

  Sequential cross-linking leads to CuAAC phase-directed protein–protein coupling.

  连续交联导致CuAAC相向蛋白质耦合。
• Multifunctional crosslinking reagents for hemoglobin, and crosslinked
  申请人：——

  公开号：US05811521A1

  公开（公告）日：1998-09-22

  Multifunctional chemical reagents useful in cross-linking hemoglobin and having the capability of leaving two or more reaction sites available for further chemical reactions, after completion of the cross-linking process. These reagents are broadly defied as aromatic compounds comprising an aromatic nucleus including but not limited phenyl, biphenyl, naphthyl and binaphthyl, with at least four independently selected electronegative substituent groups bonded directly or indirectly to the aromatic nucleus.

  这段话的中文翻译如下： 多功能化学试剂可用于交联血红蛋白，并具有在交联过程完成后留下两个或更多反应位点可用于进一步化学反应的能力。这些试剂被广泛定义为芳香族化合物，包括但不限于苯基、联苯基、萘基和联萘基，其芳香环上至少有四个独立选择的电负取代基直接或间接结合。