2-O-(trifluoromethanesulfonyloxy)-3-hydroxynaphthalene | 342890-35-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-O-(trifluoromethanesulfonyloxy)-3-hydroxynaphthalene
• 英文别名: 3-(trifluoromethylsulfonyl)naphth-2-ol；3-hydroxynaphthalen-2-yl trifluoromethanesulfonate；hydroxynaphthalen-2-yl trifluoromethanesulfonate；(3-hydroxynaphthalen-2-yl) trifluoromethanesulfonate
• CAS: 342890-35-1
• 化学式: C₁₁H₇F₃O₄S
• 分子量: 292.235
• InChiKey: GAZSQAKBIXFBLP-UHFFFAOYSA-N

物化性质

• 沸点：
  385.9±42.0 °C(Predicted)
• 密度：
  1.593±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  72
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-O-(trifluoromethanesulfonyloxy)-3-hydroxynaphthalene 在 1,1'-双(二苯基膦)二茂铁 、 甲酸 、 palladium diacetate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 以91%的产率得到2-萘酚
  参考文献：
  名称：

  以HCO2H为氢源的均相钯催化选择性还原2,2'-双酚

  摘要：

  报道了通过以HCO 2 H作为氢源还原芳基三氟甲磺酸酯的有效的均相钯催化的2,2'-双酚的选择性脱氧。该协议补充了当前基于氢气的多相钯/碳催化加氢方法。该方法以良好的至优异的产率提供了还原产物，其可以容易地转化为各种合成有用的分子，尤其是催化合成的配体。

  DOI：

  10.1055/a-1337-5153
• 作为产物：
  描述：

  2-O-(tert-butyldimethyl)silyl-3-hydroxynaphthalene 在 四丁基氟化铵 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 2-O-(trifluoromethanesulfonyloxy)-3-hydroxynaphthalene
  参考文献：
  名称：

  Photochemically Removable Silyl Protecting Groups

  摘要：

  Several o-phenol-containing alkoxyvinylsilanes were prepared and their photochemistry was investigated. These materials were prepared via hydrosilylation of the corresponding o-acetoxy arylacetylenes. Two major classes of photochemical processes were identified in these reactants: trans --> cia isomerization, leading to an intramolecular nucleophilic substitution process at silicon, and 1,5-silyl shift, leading to an unsymmetrical dialkoxysilane. The major outcome of this work is a novel class of photochemically removable protecting groups. Two alkyl substitutions on silicon, the dimethyl and diisopropyl, were examined. The latter is more stable and is preferred for protecting groups that must tolerate multiple steps or reagents. Protection of alcohols is generally performed starting with the arylethynyl acetate, which can be subjected to hydrosilylation, alcohol substitution, and acetate deprotection without isolation of intermediates. Two groups were studied in detail, the phenol and 2 naphthol Vinyl silane derivatives. A variety of primary and secondary alcohols were protected with these reagents. These groups can be deprotected cleanly and in high yield by irradiation from 250 to 350 nm.

  DOI：

  10.1021/ja002370t

文献信息

• Lewis Acid Mediated Electrophilic Cyanation of 2,2′-Biphenols
  作者：Wu Zhang、Wen Yang、Wanxiang Zhao

  DOI：10.1021/acs.joc.0c00458

  日期：2020.7.2

  A Lewis acid mediated electrophilic cyanation of 2,2′-biphenols with a trifluoromethanesulfonyl (Tf) protecting group is reported. The cyanation reactions with less toxic, commercially available MeSCN as a cyanating reagent afforded a range of 3-cyan-2,2′-biphenols in moderate to high yields. The use of trifluoromethanesulfonyl (Tf) as a protecting group is crucial to the success of this transformation

  报道了路易斯酸介导的具有三氟甲磺酰基（Tf）保护基的2,2'-双酚的亲电子氰化。用毒性较小的可商购的MeSCN作为氰化试剂进行氰化反应，可以中等至高收率得到一系列3-cyan-2,2'-双酚。三氟甲磺酰基（Tf）作为保护基的使用对于此转化成功至关重要。此外，氰化产物易于转化为各种合成有用的分子。该协议具有高效，出色的区域选择性和良好的官能团相容性的特点，可为合成和修饰生物活性化合物，催化剂和配体提供实用工具。
• Synthesis of 1,2-naphthalenediol derivatives by Rh-catalyzed intermolecular O H insertion reaction of 1,2-diazonaphthoquinones with water and alcohols
  作者：Mitsuru Kitamura、Kota Otsuka、Shuhei Takahashi、Tatsuo Okauchi

  DOI：10.1016/j.tetlet.2017.07.084

  日期：2017.9

  Rh(II)-catalyzed OH insertion reaction of diazonaphthoquinones with water or alocohols proceeded to yield 1,2-naphthalenediol derivatives.

  Rh（II）催化的重氮萘醌与水或醇的O H插入反应进行，生成1,2-萘二醇衍生物。
• SuFEx-enabled, chemoselective synthesis of triflates, triflamides and triflimidates
  作者：Bing-Yu Li、Lauren Voets、Ruben Van Lommel、Fien Hoppenbrouwers、Mercedes Alonso、Steven H. L. Verhelst、Wim M. De Borggraeve、Joachim Demaerel

  DOI：10.1039/d1sc06267k

  日期：——

  Sulfur(VI) Fluoride Exchange (SuFEx) chemistry has emerged as a next-generation click reaction, designed to assemble functional molecules quickly and modularly. Here, we report the ex situ generation of trifluoromethanesulfonyl fluoride (CF3SO2F) gas in a two chamber system, and its use as a new SuFEx handle to efficiently synthesize triflates and triflamides. This broadly tolerated protocol lends

  硫 ( VI ) 氟化物交换 (SuFEx) 化学已成为下一代点击反应，旨在快速、模块化地组装功能分子。在这里，我们报告了在两室系统中异位生成三氟甲磺酰氟（CF 3 SO 2 F）气体，并将其用作新的SuFEx手柄来有效合成三氟甲磺酸酯和三氟甲酰胺。这种广泛耐受的方案适​​用于肽修饰或伸缩到偶联反应中。此外，重新设计带有 S 的 S VI –F 连接器 奥 → 南 NR 取代提供了类似的三氟甲酰亚胺氟化物作为 SuFEx 亲电子试剂，其参与了罕见报道的三氟甲亚胺酯的合成。值得注意的是，实验表明 H 2 O 是实现苯酚与胺基化学选择性三氟甲磺化的关键，这一现象可以通过从头算动力学模拟通过胺的 CF 3 SO 2 F 三氟甲磺酸基化的氢键分子过渡态得到最好的解释。
• Synthesis of New Thiophene-Substituted 3,3-Diphenyl-3H-naphtho[2,1-b]pyrans by Cross-Coupling Reactions, Precursors of Photomodulated Materials
  作者：Michel Frigoli、Corinne Moustrou、André Samat、Robert Guglielmetti

  DOI：10.1002/ejoc.200300033

  日期：2003.8

  3,3-Diphenyl-3H-naphtho[2,1-b]pyrans linked to one, two, or three thiophene nuclei in different positions of the naphthalene moiety (5, 6, 8, and 9) by a covalent bond have been prepared in good yields. A Suzuki cross-coupling reaction was used with two possible strategies: chromenization before the coupling with oligothiophenes or chromenization after the coupling, the main intermediates being the

  3,3-二苯基-3H-萘并[2,1-b]吡喃通过共价键连接到萘部分（5、6、8和9）不同位置的一个、两个或三个噻吩核以良好的产量制备。Suzuki 交叉偶联反应用于两种可能的策略：与低聚噻吩偶联前的铬烯化或偶联后的铬烯化，主要中间体是二苯基炔丙醇、官能化萘酚衍生物和噻吩硼酸酯。获得此类光致变色化合物的总产率通常非常令人满意。对于 7 位，使用四氢萘酮衍生物和噻吩溴镁中间体之间的格利雅反应实现了偶联反应。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
• Photochemically Removable Silyl Protecting Groups
  作者：Michael C. Pirrung、Lara Fallon、Jin Zhu、Yong Rok Lee

  DOI：10.1021/ja002370t

  日期：2001.4.1

  Several o-phenol-containing alkoxyvinylsilanes were prepared and their photochemistry was investigated. These materials were prepared via hydrosilylation of the corresponding o-acetoxy arylacetylenes. Two major classes of photochemical processes were identified in these reactants: trans --> cia isomerization, leading to an intramolecular nucleophilic substitution process at silicon, and 1,5-silyl shift, leading to an unsymmetrical dialkoxysilane. The major outcome of this work is a novel class of photochemically removable protecting groups. Two alkyl substitutions on silicon, the dimethyl and diisopropyl, were examined. The latter is more stable and is preferred for protecting groups that must tolerate multiple steps or reagents. Protection of alcohols is generally performed starting with the arylethynyl acetate, which can be subjected to hydrosilylation, alcohol substitution, and acetate deprotection without isolation of intermediates. Two groups were studied in detail, the phenol and 2 naphthol Vinyl silane derivatives. A variety of primary and secondary alcohols were protected with these reagents. These groups can be deprotected cleanly and in high yield by irradiation from 250 to 350 nm.