2-(toluene-4-sulfonyl)-[1,4]naphthoquinone | 40852-77-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(toluene-4-sulfonyl)-[1,4]naphthoquinone
• 英文别名: 2-(toluene-4-sulfonyl)[1,4]naphthoquinone；2-tosylnaphthalene-1,4-dione；2-(Toluol-4-sulfonyl)-[1,4]naphthochinon；2-[4-Toluenesulfonyl]-1,4-naphthoquinone；2-(4-methylphenyl)sulfonylnaphthalene-1,4-dione
• CAS: 40852-77-5
• 化学式: C₁₇H₁₂O₄S
• 分子量: 312.346
• InChiKey: UCFUGRHGHVYUOA-UHFFFAOYSA-N

物化性质

• 熔点：
  166 °C(Solv: toluene (108-88-3))
• 沸点：
  525.4±50.0 °C(Predicted)
• 密度：
  1.393±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 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：
  76.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  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
• 作为产物：
  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

文献信息

• Ir-catalyzed C–S coupling of quinones with sulfonyl chloride
  作者：Long Wang、Yi-Bi Xie、Quan-Li Yang、Ming-Guo Liu、Kai-Bo Zheng、Yu-lin Hu、Nian-Yu Huang

  DOI：10.1007/s13738-016-0897-8

  日期：2016.10

  AbstractA concise, efficient method to sulfonyl quinones and sulfonyl-1,4-diols through Ir-catalyzed C–S coupling of quinones with sulfonyl chloride has been developed. Thus, this methodology proves its value as a versatile synthetic tool for a broad range of sulfonyl quinones, producing good to excellent yields. Graphical Abstract

  摘要已开发出一种简洁有效的方法，可通过Ir催化的醌与磺酰氯的C–S偶联来制备磺酰醌和磺酰1，，4-二醇。因此，该方法论证明了其作为广泛的磺酰基醌的通用合成工具的价值，可产生良好或优异的收率。 图形概要
• 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.
• An Optical Method for the Study of Reversible Organic Oxidation—Reduction Systems. III. Preparation and Use of a New Optically Active Standard
  作者：D. E. Kvalnes

  DOI：10.1021/ja01318a039

  日期：1934.3
• 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 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
  作者：Bingyang Ge、Dawei Wang、Weifu Dong、Piming Ma、Yongliang Li、Yuqiang Ding

  DOI：10.1016/j.tetlet.2014.08.023

  日期：2014.10

  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.