2-(2-methylsulfonyl)naphthalene-1,4-diol | 31688-66-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(2-methylsulfonyl)naphthalene-1,4-diol
• 英文别名: 2-(methanesulfonyl)-naphth-1,4-diol；2-(1.4-Dihydroxynaphthyl)methylsulfon；2-(Methylsulfonyl)naphthalene-1,4-diol；2-methylsulfonylnaphthalene-1,4-diol
• CAS: 31688-66-1
• 化学式: C₁₁H₁₀O₄S
• 分子量: 238.264
• InChiKey: LDKPKJBNGZYJSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 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：

  甲磺酰肼 、 1,4-萘醌 以 水 为溶剂， 反应 12.0h， 以75%的产率得到2-(2-methylsulfonyl)naphthalene-1,4-diol
  参考文献：
  名称：

  一种磺酰基氢醌类化合物的制备方法

  摘要：

  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。

  公开号：

  CN106565554B

文献信息

• 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.
• Bertilsson,B.-M. et al., Acta Chemica Scandinavica (1947), 1970, vol. 24, p. 3590 - 3598
  作者：Bertilsson,B.-M. et al.

  DOI：——

  日期：——
• 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。