4-methyl-N-(oxiran-2-ylmethyl)benzenesulfonamide | 5997-56-8

• 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: 4-methyl-N-(oxiran-2-ylmethyl)benzenesulfonamide
• CAS: 5997-56-8
• 化学式: C₁₀H₁₃NO₃S
• 分子量: 227.284
• InChiKey: JYNOTASVIQWSJV-UHFFFAOYSA-N

物化性质

• 熔点：
  65-67 °C
• 沸点：
  374.2±44.0 °C(Predicted)
• 密度：
  1.286±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  67.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-methyl-N-(oxiran-2-ylmethyl)benzenesulfonamide 在 sodium hydroxide 作用下， 反应 0.08h， 以95%的产率得到N-(p-toluenesulfonyl)-2-hydroxymethylaziridine
  参考文献：
  名称：

  m-CPBA介导的N-磺酰基氨基烯烃的分子内氨基羟化反应以合成β-羟基环胺

  摘要：

  各种结构多样的N磺酰基保护的氨基烯烃容易与m- CPBA反应，通过分子内氨基羟基化反应以高收率产生一系列β-羟基环胺。这种无金属且易于处理的合成方法为烯烃的邻位双官能化提供了一种环境友好的替代方法。

  DOI：

  10.1002/jhet.2169
• 作为产物：
  描述：

  1-iodo-3-(4-methylphenylsulfonamido)propan-2-yl benzoate 在 甲醇 、 potassium carbonate 作用下， 反应 12.0h， 以80%的产率得到4-methyl-N-(oxiran-2-ylmethyl)benzenesulfonamide
  参考文献：
  名称：

  NIS-mediated ring-closure/opening cascade reactions of allylamides: an expedient route to oxazolines

  摘要：

  An unprecedented NIS-mediated ring-closure/opening cascade reaction of allylamides is developed. The substrates with various functionalities were well tolerated and the scope can be extended to allylic carboxylates. Notably, the resulting iodinated chain products are versatile building blocks for the synthesis of oxazolines and epoxides. Furthermore, propargylamides can also undergo this reaction smoothly, providing the corresponding diiodoketones in good yields. The protocol offers a value route to explore new reaction patterns of other functionalized alkenes or alkynes. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.07.011

文献信息

• Regio- and chemoselective rearrangement of terminal epoxides into methyl alkyl and aryl ketones
  作者：Yingying Tian、Eva Jürgens、Doris Kunz

  DOI：10.1039/c8cc06503a

  日期：——

  The development of the highly active pincer-type rhodium catalyst 2 for the nucleophilic Meinwald rearrangement of functionalised terminal epoxides into methyl ketones under mild conditions is presented. An excellent regio- and chemoselectivity is obtained for the first time for aryl oxiranes.

  提出了在温和条件下将官能化的末端环氧化物亲核性迈恩瓦尔德重排成甲基酮的高活性钳型铑催化剂2的开发。芳基环氧乙烷首次获得了优异的区域选择性和化学选择性。
• Copper-Catalyzed Trifluoromethylation and Cyclization of Aromatic-Sulfonyl-Group-Tethered Alkenes for the Construction of 1,2-Benzothiazinane Dioxide Type Compounds
  作者：Xiang Dong、Rui Sang、Qiang Wang、Xiang-Ying Tang、Min Shi

  DOI：10.1002/chem.201303623

  日期：2013.12.9

  A multi‐talented system: An efficient copper‐catalyzed tandem trifluoromethylation/annulation of an electron‐deficient aromatic ring has been developed. This method provides a powerful and straightforward way to synthesize trifluoromethylated 1,2‐benzothiazinane dioxides under mild conditions (see scheme). The mechanism was investigated by a series of kinetic experiments and isotopic labeling studies

  多才多艺的系统：已开发出一种有效的铜催化串联的三氟甲基化/电子缺陷型芳香环的环。该方法提供了一种在温和的条件下合成三氟甲基化的1,2-苯并噻嗪烷二氧化物的强大而直接的方法（请参见方案）。通过一系列动力学实验和同位素标记研究研究了该机制。
• Nucleophilic Isomerization of Epoxides by Pincer‐Rhodium Catalysts: Activity Increase and Mechanistic Insights
  作者：Yingying Tian、Eva Jürgens、Katharina Mill、Ronja Jordan、Theo Maulbetsch、Doris Kunz

  DOI：10.1002/cctc.201900594

  日期：2019.8.21

  present the efficient isomerization of epoxides into methyl ketones with a novel pincer‐rhodium complex under very mild conditions. The catalyst system has an excellent functional group tolerance and a wide array of epoxides was tested. The corresponding methyl ketones were obtained in very high yields with excellent chemo‐ and regioselectivity. In addition, we investigated mechanistic details like the isomerization

  在此，我们介绍了在非常温和的条件下用新型的pin铑络合物将环氧化物有效异构化为甲基酮的方法。该催化剂体系具有出色的官能团耐受性，并测试了多种环氧化物。相应的甲基酮以很高的收率获得，具有出色的化学和区域选择性。此外，我们研究了催化剂异构化等机理细节，并获得了证据，表明环氧化物的亲核开环后，催化循环遵循β-氢化物消除-还原消除途径。
• Substrate-Controlled Product Divergence: Conversion of CO₂ into Heterocyclic Products
  作者：Jeroen Rintjema、Roel Epping、Giulia Fiorani、Eddy Martín、Eduardo C. Escudero-Adán、Arjan W. Kleij

  DOI：10.1002/anie.201511521

  日期：2016.3.14

  Substituted epoxy alcohols and amines allow substrate‐controlled conversion of CO2 into a wide range of heterocyclic structures through different mechanistic manifolds. This new approach results in an unusual scope of CO2‐derived products by initial activation of CO2 through either the amine or alcohol unit, thus providing nucleophiles for intramolecular epoxy ring opening under mild reaction conditions

  取代的环氧醇和胺可通过不同的机械歧管，将底物控制的CO 2转化为多种杂环结构。这种新方法通过胺或醇单元对CO 2的初始活化，导致了源自CO 2衍生产品的异常范围，从而在温和的反应条件下为分子内环氧开环提供了亲核试剂。对照实验通过遵循S N i途径的亲核试剂开环步骤和5-exo-tet环化作用，支持了胺/醇片段在该过程中的关键作用，从而形成了杂环骨架。
• Synthesis of thiazolidine-thiones, imino-thiazolidines and oxazolidines <i>via</i> the base promoted cyclisation of epoxy-sulfonamides and heterocumulenes
  作者：Mandala Anitha、K. C. Kumara Swamy

  DOI：10.1039/c7ob02915b

  日期：——

  Epoxy-sulfonamides react with heterocumulenes (carbon disulfide/isothiocyanates/isocyanates) in the presence of a base to afford ring expansion products in good to high yields with excellent regioselectivity. N-(2-Bromoethyl)-sulfonamides can also be employed as substrates. This reaction proceeds through a 5-exo-tet pathway without forming aziridine intermediates.

  环氧磺酰胺在碱的存在下与杂聚枯烯（二硫化碳/异硫氰酸酯/异氰酸酯）反应，以良好的收率和高收率提供极好的区域选择性的扩环产物。N-（2-溴乙基） -磺酰胺也可以用作底物。该反应通过5 -exo-tet途径进行，而没有形成氮丙啶中间体。