N-(4-methylphenylethynyl)-S-methyl-S-phenylsulfoximine | 1429402-63-0

• 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-(4-methylphenylethynyl)-S-methyl-S-phenylsulfoximine
• 英文别名: Methyl-[2-(4-methylphenyl)ethynylimino]-oxo-phenyl-lambda6-sulfane；methyl-[2-(4-methylphenyl)ethynylimino]-oxo-phenyl-λ6-sulfane
• CAS: 1429402-63-0
• 化学式: C₁₆H₁₅NOS
• 分子量: 269.367
• InChiKey: SOVRODCMIYVCCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  37.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(4-methylphenylethynyl)-S-methyl-S-phenylsulfoximine 、 异丁酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以80%的产率得到N-(2-(4-methylphenyl)-4,4-dimethyl-3-oxocyclobut-1-en-1-yl)-S,S-methylphenylsulfoximine
  参考文献：
  名称：

  Exploring the Reactivity ofN-Alkynylated Sulfoximines: [2 + 2]-Cycloadditions

  摘要：

  To assess the potential of N-alkynylated sulfoximines as new (chiral) reagents for organic synthesis, their reactivity profile in numerous synthetic processes is under investigation. When reacted with ketenes, the alkynylated-sulfoximines undergo a [2 + 2]-cycloaddition process to afford sulfoximine-functionalized cyclobutenones in excellent yields.

  DOI：

  10.1021/ol4026028
• 作为产物：
  描述：

  1-(2,2-二溴乙烯)-4-甲基苯 在 1,10-菲罗啉 、 苄基三乙基氯化铵 、 copper diacetate 、 potassium carbonate 、 potassium hydroxide 作用下， 以 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 53.0h， 生成 N-(4-methylphenylethynyl)-S-methyl-S-phenylsulfoximine
  参考文献：
  名称：

  铜催化的亚砜亚砜与溴乙炔的N-炔基化反应

  摘要：

  Ñ -Alkynylated亚磺酰亚胺已通过从开始铜催化的交叉偶联反应得到Ñ H-亚磺酰亚胺和bromoacetylenes在中度至良好的产率。反应条件温和，底物范围广。

  DOI：

  10.1021/ol5016898

文献信息

• Copper-Catalyzed Oxidative Decarboxylative Couplings of Sulfoximines and Aryl Propiolic Acids
  作者：Daniel L. Priebbenow、Peter Becker、Carsten Bolm

  DOI：10.1021/ol403106e

  日期：2013.12.20

  A method has been developed for the preparation of N-alkynylated sulfoximines involving the copper-catalyzed decarboxylative coupling of sulfoximines with aryl propiolic acids. A range of substituents on both the sulfoximidoyl moiety and the aryl group of the propiolic acid were compatible with this reaction process to afford a series of sulfoximidoyl-functionalized alkynes.

  已经开发了一种用于制备N-炔基化亚砜基的方法，该方法涉及亚砜基与芳基丙酸的铜催化的脱羧偶联。丙二酸的亚磺酰亚胺基部分和芳基上的一系列取代基与该反应过程相容，从而提供了一系列由亚磺酰亚胺基官能化的炔烃。
• Synthesis of Sulfoximidoyl-Containing Hypervalent Iodine(III) Reagents and Their Use in Transition-Metal-Free Sulfoximidations of Alkynes
  作者：Han Wang、Ying Cheng、Peter Becker、Gerhard Raabe、Carsten Bolm

  DOI：10.1002/anie.201605743

  日期：2016.10.4

  hypervalent iodine(III) reagents incorporating transferable sulfoximidoyl groups were obtained through ligand exchange reactions of methoxy(tosyloxy)iodobenzene (MTIB) with NH sulfoximines in good to excellent yields. The solid‐state structure of a representative product was characterized by X‐ray crystallography. Utilizing these reagents in synthesis provides a new, transition‐metal‐free approach towards

  通过甲氧基（甲苯磺酰氧基）碘代苯（MTIB）与NH亚砜亚胺的配体交换反应，可以很好地获得具有可转移的亚磺酰亚胺基的明确定义的高价碘试剂。代表性产品的固态结构通过X射线晶体学表征。在合成中使用这些试剂为N-炔基化亚砜亚胺提供了一种新的无过渡金属的方法。
• Copper-Catalyzed Oxidative Cross-Coupling of Sulfoximines and Alkynes
  作者：Long Wang、He Huang、Daniel L. Priebbenow、Fang-Fang Pan、Carsten Bolm

  DOI：10.1002/anie.201209975

  日期：2013.3.18
• Copper-Catalyzed <i>N</i>-Alkynylations of Sulfoximines with Bromoacetylenes
  作者：Xiao Yun Chen、Long Wang、Marcus Frings、Carsten Bolm

  DOI：10.1021/ol5016898

  日期：2014.7.18

  N-Alkynylated sulfoximines have been obtained by copper-catalyzed cross-coupling reactions starting from NH-sulfoximines and bromoacetylenes in moderate to good yields. The reaction conditions are mild, and the substrate scope is wide.

  Ñ -Alkynylated亚磺酰亚胺已通过从开始铜催化的交叉偶联反应得到Ñ H-亚磺酰亚胺和bromoacetylenes在中度至良好的产率。反应条件温和，底物范围广。
• Exploring the Reactivity of<i>N</i>-Alkynylated Sulfoximines: [2 + 2]-Cycloadditions
  作者：Ramona Pirwerdjan、Daniel L. Priebbenow、Peter Becker、Philip Lamers、Carsten Bolm

  DOI：10.1021/ol4026028

  日期：2013.11

  To assess the potential of N-alkynylated sulfoximines as new (chiral) reagents for organic synthesis, their reactivity profile in numerous synthetic processes is under investigation. When reacted with ketenes, the alkynylated-sulfoximines undergo a [2 + 2]-cycloaddition process to afford sulfoximine-functionalized cyclobutenones in excellent yields.