N-(phenylsulfonyl)-4-(trifluoromethyl)benzamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(phenylsulfonyl)-4-(trifluoromethyl)benzamide
• 英文别名: N-(benzenesulfonyl)-4-(trifluoromethyl)benzamide
• 化学式: C₁₄H₁₀F₃NO₃S
• 分子量: 329.3
• InChiKey: DLQRVSFCDQUPNF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(phenylsulfonyl)-4-(trifluoromethyl)benzamide 在 lithium hydroxide monohydrate 、 fluorine 、 sodium fluoride 作用下， 以 丙酮 、 乙腈 为溶剂， 反应 12.33h， 以51%的产率得到N-fluoro-N-(phenylsulfonyl)-4-(trifluoromethyl)benzamide
  参考文献：
  名称：

  用于甲硅烷醇醚的高选择性单氟化和二氟化的台式稳定亲电氟化试剂

  摘要：

  最近，人们对合成含氟化合物的有效方法进行了深入研究。为此，开发实用的氟化试剂是必不可少的。在此，工作台稳定的亲电子氟化试剂被合成为N-氟苯磺酰亚胺(NFSI) 替代品。通过用酰基取代 NFSI 磺酰基之一获得的试剂导致甲硅烷基烯醇醚的高度选择性单氟化，同时抑制了不希望的过度反应，即二氟化。另一方面，在 NFSI 苯磺酰基上带有吸电子取代基的试剂在无碱条件下有效地促进了甲硅烷基烯醇醚的二氟化。因此，单氟化和二氟化靶材料均由同一基材制备。

  DOI：

  10.1002/chem.202101499
• 作为产物：
  描述：

  苯磺酰胺 、 4-三氟甲基苯甲酰氯 在 吡啶 作用下， 以 乙腈 为溶剂， 反应 0.33h， 以5%的产率得到N-(phenylsulfonyl)-4-(trifluoromethyl)benzamide
  参考文献：
  名称：

  β-Keto sulfones as inhibitors of 11β-hydroxysteroid dehydrogenase type I and the mechanism of action

  摘要：

  The design, synthesis, and biological evaluation of beta-keto sulfones as 11 beta-HSD1 inhibitors and the mechanism of inhibition are described here. This class of compounds is not active against 11 beta-HSD2 and therefore may have therapeutic potential for metabolic syndrome and type 2 diabetes. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.04.035

文献信息

• β-Keto sulfones as inhibitors of 11β-hydroxysteroid dehydrogenase type I and the mechanism of action
  作者：Jason Xiang、Manus Ipek、Vipin Suri、May Tam、Yuzhe Xing、Nelson Huang、Yanling Zhang、James Tobin、Tarek S. Mansour、John McKew

  DOI：10.1016/j.bmc.2007.04.035

  日期：2007.7

  The design, synthesis, and biological evaluation of beta-keto sulfones as 11 beta-HSD1 inhibitors and the mechanism of inhibition are described here. This class of compounds is not active against 11 beta-HSD2 and therefore may have therapeutic potential for metabolic syndrome and type 2 diabetes. (c) 2007 Elsevier Ltd. All rights reserved.
• METHODS AND COMPOSITIONS FOR TREATING ALCOHOL USE DISORDERS
  申请人：SANNA Pietro Paolo

  公开号：US20170232007A1

  公开（公告）日：2017-08-17

  Disclosed are methods and compositions for treating alcohol dependence by administration to a patient of an inhibitor of 11β-hydroxysteroid dehydrogenases (11β-HSD) to modulate glucocorticoid effects. One such compound is the 11β-HSD inhibitor carbenoxolone (18β-glycyrrhetinic acid 3β-O-hemisuccinate), which has been extensively employed in the clinic for the treatment of gastritis and peptic ulcer. Carbenoxolone is active on both 11β-HSD1 and 2 isoforms. Here, carbenoxolone is surprisingly shown to reduce both baseline and excessive drinking in rats and mice. The carbenoxolone diastereomer 18α-glycyrrhetinic acid 3β-O-hemisuccinate (αCBX), which the applicants discovered to be selective for 11β-HSD2, was also effective in reducing alcohol drinking in mice. Thus, 11β-HSD inhibitors are a new class of candidate alcohol abuse medications and existing 11β-HSD inhibitor drugs may be re-purposed for alcohol abuse treatment.
• Bench‐Stable Electrophilic Fluorinating Reagents for Highly Selective Mono‐ and Difluorination of Silyl Enol Ethers
  作者：Akiya Adachi、Kohsuke Aikawa、Yuichiro Ishibashi、Kyoko Nozaki、Takashi Okazoe

  DOI：10.1002/chem.202101499

  日期：2021.8.16

  the synthesis of fluorinated compounds have been intensively studied, recently. Development of practical fluorinating reagents is indispensable for this purpose. Herein, bench-stable electrophilic fluorinating reagents were synthesized as N-fluorobenzenesulfonimide (NFSI) substitutes. Reagents obtained by replacing one of the NFSI sulfonyl groups with an acyl group led to the highly selective monofluorination

  最近，人们对合成含氟化合物的有效方法进行了深入研究。为此，开发实用的氟化试剂是必不可少的。在此，工作台稳定的亲电子氟化试剂被合成为N-氟苯磺酰亚胺(NFSI) 替代品。通过用酰基取代 NFSI 磺酰基之一获得的试剂导致甲硅烷基烯醇醚的高度选择性单氟化，同时抑制了不希望的过度反应，即二氟化。另一方面，在 NFSI 苯磺酰基上带有吸电子取代基的试剂在无碱条件下有效地促进了甲硅烷基烯醇醚的二氟化。因此，单氟化和二氟化靶材料均由同一基材制备。
• Development of an Acyl Sulfonamide Anti-Proliferative Agent, LY573636·Na
  作者：Matthew H. Yates、Neil J. Kallman、Christopher P. Ley、Jeffrey N. Wei

  DOI：10.1021/op800210x

  日期：2009.3.20

  The synthesis of 5-bromo-thiophene-2-sulfonic acid 2,4-dichlorobenzoylamide sodium salt on multikilogram scale is described. The initial clinical supplies were made using carbonyl diimidazole to converge the two fragments. A more efficient acid chloride process has been developed, which also provides better control of impurities and color throughout the synthesis.