4-nitro-N-(2-oxo-2-phenylethyl)benzenesulfonamide | 55158-96-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-nitro-N-(2-oxo-2-phenylethyl)benzenesulfonamide
• 英文别名: N-(p-nitrobenzenesulfonamido)-acetophenone；4-nitro-N-phenacylbenzenesulfonamide
• CAS: 55158-96-8
• 化学式: C₁₄H₁₂N₂O₅S
• 分子量: 320.326
• InChiKey: MQIPTPLXIDLWNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-nitro-N-(2-oxo-2-phenylethyl)benzenesulfonamide 在 (5aR,10bS)-5a,10b-dihydro-2-(2,4,6-trimethylphenyl)-4H,6H-indeno[2,1-b]-1,2,4-triazolo[4,3-d]-1,4-oxazinium chloride 、 sodium thiophenolate 、 potassium carbonate 、 三乙胺 作用下， 以 1,4-二氧六环 、 二甲基亚砜 、 乙腈 为溶剂， 反应 24.0h， 生成 (4R,5S)-5-benzoyl-4-phenylpyrrolidin-2-one
  参考文献：
  名称：

  N-杂环卡宾促进不对称合成对映体富集的6-羟基丁内酰胺

  摘要：

  在本文中，已经成功地通过N-杂环卡宾催化的溴化烯与α-氨基酮的正式[3 + 2]环合，然后还原的方法成功开发了合成6-羟基丁内酰胺的有效途径。值得注意的是，对映体富集的epi -neoclausenamide，这是黄皮衍生物之一，可以有效地通过该策略制备。

  DOI：

  10.1021/acs.joc.9b01490
• 作为产物：
  描述：

  α-methoxystyrene 在 盐酸 、 乙醇 作用下， 生成 4-nitro-N-(2-oxo-2-phenylethyl)benzenesulfonamide
  参考文献：
  名称：

  Semenov,V.P. et al., Journal of Organic Chemistry USSR (English Translation), 1975, vol. 11, p. 291 - 295

  摘要：

  DOI：

文献信息

• Synthesis of α-Substituted Vinylsulfonium Salts and Their Application as Annulation Reagents in the Formation of Epoxide- and Cyclopropane-Fused Heterocycles
  作者：Johnathan V. Matlock、Sven P. Fritz、Stephen A. Harrison、Diane M. Coe、Eoghan M. McGarrigle、Varinder K. Aggarwal

  DOI：10.1021/jo501885z

  日期：2014.11.7

  methods for the synthesis of classes of potentially bioactive molecules remains an important goal for synthetic chemists. Vinylsulfonium salts have been used for the synthesis of a wide variety of small heterocyclic motifs; however, further developments to this important class of reagents has been focused on reaction with new substrates rather than development of new vinylsulfonium salts. We herein report

  发现合成潜在生物活性分子类别的新方法仍然是合成化学家的重要目标。乙烯基锍盐已用于合成多种小的杂环基序；然而，对这类重要试剂的进一步开发集中在与新底物的反应上，而不是开发新的乙烯基锍盐。我们在此报告了一系列 α-取代的乙烯基锍四苯基硼酸盐（10 个例子）的合成，该过程采用 3 步程序从市售的苯乙烯中获得。还详细介绍了四苯基硼酸盐抗衡离子对乙烯基锍盐的稳定性和可及性的重要作用。α-取代的四苯基硼酸乙烯基锍在 β-氨基酮的环氧环化反应（15 个实施例）和烯丙基胺的环丙烷化反应（4 个实施例）中产生了良好的产率。环氧环化产物的氢化以良好的非对映选择性进行。
• Novel three-component synthesis and antiproliferative properties of diversely functionalized pyrrolines
  作者：Igor V. Magedov、Giovanni Luchetti、Nikolai M. Evdokimov、Madhuri Manpadi、Wim F.A. Steelant、Severine Van slambrouck、Paul Tongwa、Mikhail Yu. Antipin、Alexander Kornienko

  DOI：10.1016/j.bmcl.2008.01.019

  日期：2008.2

  Diversely substituted 2-pyrrolines have been prepared by a novel multicomponent process involving a reaction of various N-(aryl- and alkylsulfonamido)-acetophenones with aldehydes and malononitrile. While the reaction is highly regioselective, it is not stereoselective, generating a mixture of cis and trans 2-pyrrolines. A number of analogs from both cis and trans 2-pyrroline libraries were found to have antiproliferative activity in human cancer cell lines. (c) 2008 Elsevier Ltd. All rights reserved.
• One-Pot Multicomponent Synthesis of Diversely Substituted 2-Aminopyrroles. A Short General Synthesis of Rigidins A, B, C, and D
  作者：Liliya V. Frolova、Nikolai M. Evdokimov、Kathryn Hayden、Indranil Malik、Snezna Rogelj、Alexander Kornienko、Igor V. Magedov

  DOI：10.1021/ol103149b

  日期：2011.3.4

  Privileged medicinal scaffolds based on the structures of tetra- and pentasubstituted 2-aminopyrroles were prepared via one-pot multicomponent reactions of structurally diverse aldehydes and N-(aryl-, hetaryl-, alkylsulfonamido)acetophenones with activated methylene compounds. This methodology was used in a four-step synthesis of alkaloids rigidins A, B, C, and Din overall yields of 61%, 58%, 60%, and 53%, respectively. Of these, rigidins B, C, and D were synthesized for the first time.
• Semenov,V.P. et al., Journal of Organic Chemistry USSR (English Translation), 1975, vol. 11, p. 291 - 295
  作者：Semenov,V.P. et al.

  DOI：——

  日期：——
• Asymmetric Synthesis of Enantioenriched 6-Hydroxyl Butyrolactams Promoted by N-Heterocyclic Carbene
  作者：Zhouli Hu、Ying Zhu、Zhenqian Fu、Wei Huang

  DOI：10.1021/acs.joc.9b01490

  日期：2019.8.16

  Herein, an efficient route to synthesize 6-hydroxyl butyrolactams has been successfully developed via an N-heterocyclic carbene-catalyzed formal [3 + 2] annulation of bromoenals with α-amino ketones, followed by reduction. Remarkably, enantioenriched epi-neoclausenamide, which is one of the clausenamide derivatives, could be efficiently prepared by this strategy.

  在本文中，已经成功地通过N-杂环卡宾催化的溴化烯与α-氨基酮的正式[3 + 2]环合，然后还原的方法成功开发了合成6-羟基丁内酰胺的有效途径。值得注意的是，对映体富集的epi -neoclausenamide，这是黄皮衍生物之一，可以有效地通过该策略制备。