N-phenylethynyl-S-methyl-S-methylsulfoximine | 86734-33-0

• 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-phenylethynyl-S-methyl-S-methylsulfoximine
• 英文别名: N-(phenylethynyl)-S,S-dimethylsulphoximine；N-(phenylethynyl)-S,S-dimethylsulfoximine；({[Dimethyl(oxo)-lambda~6~-sulfanylidene]amino}ethynyl)benzene；dimethyl-oxo-(2-phenylethynylimino)-λ6-sulfane
• CAS: 86734-33-0
• 化学式: C₁₀H₁₁NOS
• 分子量: 193.269
• InChiKey: ZTEZBXVGUPALRI-UHFFFAOYSA-N

物化性质

• 熔点：
  103-104 °C
• 沸点：
  310.5±25.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  异丁酰氯 、 N-phenylethynyl-S-methyl-S-methylsulfoximine 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以61%的产率得到N-(2-phenyl-4,4-dimethyl-3-oxocyclobut-1-en-1-yl)-S,S-dimethylsulfoximine
  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：

  二甲基亚磺酰亚胺 、 苯乙炔 在 吡啶 、 氧气 、 sodium carbonate 、 copper dichloride 作用下， 以 1,4-二氧六环 为溶剂， 70.0 ℃ 、101.33 kPa 条件下， 反应 18.0h， 以58%的产率得到N-phenylethynyl-S-methyl-S-methylsulfoximine
  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

文献信息

• 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。
• Nucleophilic attack on chloro(phenyl)ethyne by azide ion
  作者：Ryuichi Tanaka、Kuniaki Yamabe

  DOI：10.1039/c39830000329

  日期：——

  The reaction of chloro(phenyl)ethyne (1) with sodium azide in dimethyl sulphoxide gave the nucleophilic addition product (Z)-α-azido-β-chlorostyrene; phenylethynylnitrane (7) was trapped by the solvent to give N-(phenylethynyl)-S,S-dimethylsulphoximine (4), indicating the prior formation of the hitherto unknown substitution product azido(phenyl)ethyne (6).

  氯（苯基）乙炔（1）与叠氮化钠在二甲亚砜中反应，得到亲核加成产物（Z）-α-叠氮基-β-氯苯乙烯。苯乙炔基硝烷（7）被溶剂捕获，得到N-（苯乙炔基）-S，S-二甲基亚磺酰亚胺（4），表明先前形成的迄今未知的取代产物叠氮基（苯基）乙炔（6）。
• TANAKA, RYUICHI;YAMABE, KUNIAKI, J. CHEM. SOC. CHEM. COMMUN., 1983, N 7, 329-330
  作者：TANAKA, RYUICHI、YAMABE, KUNIAKI

  DOI：——

  日期：——
• 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.