2-(morpholinosulfonyl)-1-phenylethan-1-one | 110417-55-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(morpholinosulfonyl)-1-phenylethan-1-one
• 英文别名: 2-(4-Morpholinylsulfonyl)-1-phenylethanone；2-morpholin-4-ylsulfonyl-1-phenylethanone
• CAS: 110417-55-5
• 化学式: C₁₂H₁₅NO₄S
• 分子量: 269.321
• InChiKey: QFVXFSIJYVUTPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(morpholinosulfonyl)-1-phenylethan-1-one 在 钾硼氢 作用下， 以 甲醇 为溶剂， 反应 2.5h， 生成 N-<(2-hydroxy-2-phenylethyl)sulfonyl>morpholine
  参考文献：
  名称：

  Gayral; Loiseau; Bories, Arzneimittel-Forschung/Drug Research, 1995, vol. 45, # 10, p. 1122 - 1127

  摘要：

  DOI：
• 作为产物：
  描述：

  反-β-苯乙烯磺酰氯 在 palladium on activated charcoal sodium hypophosphite 、 potassium tert-butylate 、 溴 、 三乙胺 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 叔丁醇 为溶剂， 反应 23.0h， 生成 2-(morpholinosulfonyl)-1-phenylethan-1-one
  参考文献：
  名称：

  New antifilarial agents. 1. Epoxy sulfonamides and ethynesulfonamides

  摘要：

  Two series of 2-substituted 1,2-epoxyethanesulfonamides 2 and ethynesulfonamides 5 were synthesized and evaluated for their antifilarial activity. The trans epoxides 2T were stereospecifically prepared by a Darzens reaction between aldehydes and halomethanesulfonamides. The cis isomers 2c were obtained from ethynesulfonamides 5 by semihydrogenation followed by KOCl epoxidation. 2-Substituted ethynesulfonamides 5 were synthesized from appropriate trans-ethenesulfonamides by a bromination/dehydrobromination sequence. These products, as well as several synthetic intermediates, were evaluated for antifilarial activity against Molinema dessetae either in vivo in its natural host, the rodent Proechimys oris, or in vitro by a new test using cultures of the infective larvae. Most of the epoxides 2T and acetylenic derivatives 5 bearing a 2-aryl substituent were active in vitro. Among these compounds, four epoxides 2T and one acetylenic derivative 5 showed marked macrofilaricidal activity in vivo without any microfilaricidal activity. The differences between the in vivo and in vitro results may be due, in part, to the low chemical stability of the epoxy sulfonamides 2T. Despite this limitation, the activities observed in this reliable animal model suggest further development and testing of both series 2T and 5 as macrofilaricides.

  DOI：

  10.1021/jm00395a010

文献信息

• Photoredox-Catalyzed Generation of Sulfamyl Radicals: Sulfonamidation of Enol Silyl Ether with Chlorosulfonamide
  作者：Qiyu Luo、Runyu Mao、Yan Zhu、Yonghui Wang

  DOI：10.1021/acs.joc.9b02062

  日期：2019.11.1

  A novel and practical photoredox-catalyzed generation of sulfamyl radicals followed by radical sulfonamidation of enol silyl ether has been described. Diverse functionalized β-ketosulfonamides were prepared in modest to excellent yields under mild and economic reaction conditions through the present catalytic protocol. Furthermore, the methodology developed provides an efficient and convenient approach

  已经描述了新颖且实用的光氧化还原催化的磺酰胺基的产生，随后是烯醇甲硅烷基醚的自由基磺酰胺化。通过本发明的催化方案，在温和且经济的反应条件下以适度至优异的产率制备了多种官能化的β-酮磺酰胺。此外，开发的方法为合成抗癫痫药Zonisamide提供了一种有效而便捷的方法。
• A simple and versatile synthesis of substituted ethynesulfonamides
  作者：Martine Leclercq、Marie-Joséphe Brienne

  DOI：10.1016/s0040-4039(00)97493-8

  日期：1990.1

  A variety of substituted 2-arylethynesulfonamides were prepared by a two-step sequence: 1. preparation of 2-oxo-2-arylethanesulfonamides by reaction of the appropriate methanesulfonamide carbanion with a substituted benzoic ester, 2. dehydration of the resulting ketone by 2-chloro-N-methylpyridinium iodide / NEt3.

  通过两步操作制备了各种取代的2-芳基乙炔磺酰胺：1.通过适当的甲磺酰胺碳负离子与取代的苯甲酸酯反应制备2-氧代-2-芳基乙磺酰胺，2.通过2-脱水生成的酮氯-N-甲基吡啶碘化物/ NEt 3。
• Photo-mediated radical relay oximinosulfonamidation of alkenes with N-nitrosamines triggered by DABSO
  作者：Ji-Wei Sang、Hong Chen、Yu Zhang、Jinxin Wang、Wei-Dong Zhang

  DOI：10.1039/d4gc01976h

  日期：——

  of diverse α-oximino sulfonamides via direct photo-mediated radical relay oximinosulfonamidation of activated or unactivated alkenes with N-nitrosamines triggered by organic sulfide. N-Nitrosamines worked as bifunctional reagents in this transformation, simultaneously generating aminyl radicals and NO radicals. The organic sulfide was designed to act as a radical decaging agent as well as a source

  N-亚硝胺代表一类双功能氮自由基前体，但其应用潜力在很大程度上尚未开发。该研究报道了通过有机硫化物引发的 N-亚硝胺与活化或未活化的烯烃的直接光介导自由基中继肟基磺酰胺化，以高度原子经济的方式生产各种 α-肟基磺酰胺。 N-亚硝胺在此转化中充当双功能试剂，同时产生氨基自由基和NO自由基。有机硫化物被设计用作自由基清除剂以及磺酰基来源。其强大的自由基捕获能力和对烯烃的亲和力能够快速捕获氨基自由基，从而抑制自由基对在溶剂笼中的快速重组。合成的肟单元也可以很容易地转化为其他官能团，从而导致选择性的下游转化。有害N-亚硝胺的温和光降解反应表现出较高的官能团耐受性和相容性，有利于天然产物和药物分子的后期功能化，扩大了生物学相关的化学空间。
• Photoinduced Vicinal Sulfamoyloximation of Alkenes: Harnessing Bifunctional Nitrosamines via a Rapid Radical Trapping Strategy
  作者：Wei Li、Chenchen Diao、Yilian Lu、Huaifeng Li

  DOI：10.1021/acs.orglett.4c02245

  日期：2024.7.26

  bifunctional activation under neutral conditions to generate key sulfamoyl radicals. It accommodates broad substrate scope and functional group compatibility, enabling late-stage modifications of bioactive molecules and expanding sulfonamide diversity in organic synthesis.

  我们开发了一种使用N-亚硝胺作为双功能试剂进行烯烃邻位氨磺酰肟化的光诱导方法，其中 DABSO 既作为磺酰源又作为快速氨基自由基捕获剂。这种策略可以防止自由基重组，从而在中性条件下实现双功能激活，从而产生关键的氨磺酰自由基。它适应广泛的底物范围和官能团兼容性，能够对生物活性分子进行后期修饰并扩大有机合成中磺酰胺的多样性。
• Hepatoselectivity of statins: Design and synthesis of 4-sulfamoyl pyrroles as HMG-CoA reductase inhibitors
  作者：William K.C. Park、Robert M. Kennedy、Scott D. Larsen、Steve Miller、Bruce D. Roth、Yuntao Song、Bruce A. Steinbaugh、Kevin Sun、Bradley D. Tait、Mark C. Kowala、Bharat K. Trivedi、Bruce Auerbach、Valerie Askew、Lisa Dillon、Jeffrey C. Hanselman、Zhiwu Lin、Gina H. Lu、Andrew Robertson、Catherine Sekerke

  DOI：10.1016/j.bmcl.2007.11.124

  日期：2008.2

  4-Sulfamoyl pyrroles were designed as novel hepatoselective HMG-CoA reductase inhibitors (statins) to reduce myalgia, a statin-induced adverse effect. The compounds were prepared via a [3 + 2] cycloaddition of a Munchnone with a sulfonamide-substituted alkyne. We identified compounds with greater selectivity for hepatocytes compared to L6-myocytes than rosuvastatin and atorvastatin. There was an inverse correlation of myocyte potencies and ClogP values. A number of analogs were effective at reducing cholesterol in acute and chronic in vivo models but they lacked sufficient chronic in vivo activity to warrant further development. (C) 2007 Elsevier Ltd. All rights reserved.