2-tosylnaphthalene-1,4-diol | 40852-87-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-tosylnaphthalene-1,4-diol
• 英文别名: 2-(4-methylphenyl)sulfonylnaphthalene-1,4-diol
• CAS: 40852-87-7
• 化学式: C₁₇H₁₄O₄S
• 分子量: 314.362
• InChiKey: CYYDOKQRZQTSOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  83
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-tosylnaphthalene-1,4-diol 在 manganese(IV) oxide 作用下， 以 乙腈 为溶剂， 以80%的产率得到2-(toluene-4-sulfonyl)-[1,4]naphthoquinone
  参考文献：
  名称：

  Metal-free sulfonylation of quinones with sulfonyl hydrazides in water: Facile access to mono-sulfonylated hydroquinones

  摘要：

  This paper describes a simple and practical protocol for the direct synthesis of monosulfonylated hydroquinones through a transition-metal-free cross-coupling between quinones and sulfonyl hydrazides in water. The procedure tolerates a variety of quinones and widely available sulfonyl hydrazides. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2017.03.066
• 作为产物：
  描述：

  2-(toluene-4-sulfonyl)-[1,4]naphthoquinone 在 sodium tetrahydroborate 作用下， 反应 1.0h， 以94%的产率得到2-tosylnaphthalene-1,4-diol
  参考文献：
  名称：

  Synthesis of arylsulfonyl-quinones and arylsulfonyl-1,4-diols as FabH inhibitors: Pd-catalyzed direct C-sulfone formation by CS coupling of quinones with arylsulfonyl chloride

  摘要：

  The Pd-catalyzed direct C-sulfone formation by C-S coupling of quinones with arylsulfonyl chloride has been developed. This methodology provides an effective, convenient method for the synthesis of aryl-sulfonyl-quinones and arylsulfonyl-1,4-diols, which are potent inhibitors of FabH. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.08.023

文献信息

• Hydroxysulfonylation of Quinones with Aryl(alkyl)sulfonyl Hydrazides for the Synthesis of 1,4-Dihydroxy-2-aryl(alkyl)sulfonylbenzenes
  作者：Ping-Gui Li、Yan-Chun Li、Tao Zhu、Liang-Hua Zou、Zhimeng Wu

  DOI：10.1002/ejoc.201701199

  日期：2017.11.2

  A copper-catalyzed procedure for the direct synthesis of 1,4-dihydroxy-2-phenylsufonylbenzenes is presented starting from simple quinones and sulfonyl hydrazides. A series of biologically useful FabH inhibitors are obtained in good yields. Both aryl and alkyl substituents are well tolerated in the reaction.

  从简单的醌和磺酰肼开始，提出了铜催化直接合成1，4-二羟基-2-苯基磺酰苯的方法。以高收率获得了一系列生物学上有用的FabH抑制剂。该反应中芳基和烷基取代基均具有良好的耐受性。
• 一种磺酰基氢醌类化合物的制备方法
  申请人：上海北卡医药技术有限公司

  公开号：CN106565554B

  公开（公告）日：2018-05-15

  本发明属于有机合成领域，具体涉及一种磺酰基氢醌类化合物的制备方法。本发明的制备方法，以廉价易得的醌类化合物为原料，使用稳定易保存的磺酰肼为磺酰化试剂，采用无金属催化，环境友好的反应条件、简化了制备过程，提高了收率。
• One-pot access to sulfonylated naphthalenediols/hydroquinones from naphthols/phenols with sodium sulfinates in an aqueous medium
  作者：Lingxin Meng、Ruike Zhang、Yuqiu Guan、Tian Chen、Zhiqiang Ding、Gongshu Wang、Aikebaier Reheman、Zhangpei Chen、Jianshe Hu

  DOI：10.1039/d0nj05285j

  日期：——

  aqueous medium has been developed with up to 97% yield. The whole reaction requiring no transition-metal catalysts could proceed smoothly with hypervalent iodine compounds as the oxidant. Both naphthols and phenols were viable with inexpensive and readily available sodium sulfinates as the sulfonylation reagents under an ambient atmosphere. This procedure is scalable, and the products could be easily obtained

  已经开发出一种在水性介质中对磺酰化对苯二酚/萘二醇进行单锅法的方法，其收率高达97％。以高价碘化合物为氧化剂，不需要过渡金属催化剂的整个反应可以顺利进行。在环境气氛下，萘甲酚和苯酚都可以与廉价且易于获得的亚磺酸钠作为磺酰化试剂一起使用。此过程可扩展，无需柱色谱分离即可轻松获得产品。
• Ionic Liquids-Promoted Addition of Arylsulfinic Acids to <i>p</i>-Quinones: A Green Synthesis of Diaryl Sulfones
  作者：J. Yadav、B. Reddy、T. Swamy、N. Ramireddy

  DOI：10.1055/s-2004-829145

  日期：——

  Arylsulfinic acids undergo smooth conjugate addition to p-quinones in air- and moisture-stable second generation room temperature ionic liquid [bmim]BF 4 under mild conditions to produce the corresponding arylsulfonylhydroquinones in excellent yields with high selectivity. In this reaction, ionic liquid plays the dual role as the solvent and the catalyst. The quinones show enhanced reactivity in ionic

  芳基亚磺酸在空气和水分稳定的第二代室温离子液体 [bmim]BF 4 中在温和条件下与对醌进行平滑共轭加成，以优异的收率和高选择性生成相应的芳基磺酰基氢醌。在这个反应中，离子液体起到了溶剂和催化剂的双重作用。醌类在离子液体中表现出增强的反应性，从而缩短了反应时间并显着提高了产率。离子液体的存在有助于避免使用酸或碱催化剂进行这种转化。回收的离子液体可重复使用四到五次，活性一致。
• Electrochemical‐In‐Situ‐Oxidative Sulfonylation of Phenols with Sulfinic Acids as an Access to Sulfonylated Hydroquinones
  作者：Xue Sun、Fanjun Zhang、Kelu Yan、Wenfeng Feng、Xuejun Sun、Jianjing Yang、Jiangwei Wen

  DOI：10.1002/adsc.202100366

  日期：——

  The electrochemical in-situ oxidative sulfonylation of phenols with sulfinic acids access to sulfonylated hydroquinones has been developed. A series of sulfonylated hydroquinones were prepared under mild mediator-, catalyst- and exogenous-oxidant-free conditions. Notably, such an electrochemical in-situ-oxidative synthetic strategy presented wide functional group tolerance and amenability to gram-scale

  已经开发了苯酚与亚磺酸的电化学原位氧化磺酰化获得磺酰化氢醌。在温和的无介质、无催化剂和无外源氧化剂的条件下制备了一系列磺酰化氢醌。值得注意的是，这种电化学原位氧化合成策略表现出广泛的官能团耐受性和克级合成的适应性，产率为 62-80%。