2-((4-chlorophenyl)sulfonyl)naphthalene-1,4-diol | 1101874-41-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-((4-chlorophenyl)sulfonyl)naphthalene-1,4-diol
• 英文别名: 2-(4-Chlorophenylsulfonyl)naphthalene-1,4-diol；2-(4-chlorophenyl)sulfonylnaphthalene-1,4-diol
• CAS: 1101874-41-2
• 化学式: C₁₆H₁₁ClO₄S
• 分子量: 334.78
• InChiKey: SXWUEZFUYNUEML-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-氯苯-1-磺酰肼 、 1,4-萘醌 在 copper(II) acetate monohydrate 、 manganese(III) triacetate dihydrate 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以66%的产率得到2-((4-chlorophenyl)sulfonyl)naphthalene-1,4-diol
  参考文献：
  名称：

  苯醌与芳基（烷基）磺酰基肼的羟基磺酰化反应，用于合成1,4-二羟基-2-芳基（烷基）磺酰基苯

  摘要：

  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。

  DOI：

  10.1002/ejoc.201701199

文献信息

• 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。
• Metal-free sulfonylation of quinones with sulfonyl hydrazides in water: Facile access to mono-sulfonylated hydroquinones
  作者：Bin Li、Yaqin Li、Linqian Yu、Xiaoyu Wu、Wanguo Wei

  DOI：10.1016/j.tet.2017.03.066

  日期：2017.5

  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.
• Synthesis and biological evaluation of novel sulfonyl-naphthalene-1,4-diols as FabH inhibitors
  作者：Mamoun M. Alhamadsheh、Norman C. Waters、Sarbjot Sachdeva、Patricia Lee、Kevin A. Reynolds

  DOI：10.1016/j.bmcl.2008.10.097

  日期：2008.12

  A series of analogs of 2-tosylnaphthalene-1,4-diol were prepared and were found to be potent 10-20 nM reversible inhibitors of the Escherichia coli FabH enzyme. The inhibitors were also effective but to a lesser degree (30 nM-5 mu M), against the Mycobacterium tuberculosis and Plasmodium falciparum FabH enzymes. Preliminary SAR studies demonstrated that the sulfonyl group and naphthalene-1,4 diol were required for activity against all enzymes but the toluene portion could be significantly altered and leads to either modest increases or decreases in activity against the three enzymes. The in vitro activity of the analogs against E. coli FabH parallel the in vivo activity against E. coli TolC strain and many of the compounds were also shown to have antimalarial activity against P. falciparum. (C) 2008 Published by Elsevier Ltd.