N-[5-methylthenoyl]-S-methyl-S-phenylsulfoximine | 1616087-94-5

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: N-[5-methylthenoyl]-S-methyl-S-phenylsulfoximine
• 英文别名: 5-methyl-N-(methyl(oxo)(phenyl)-λ⁶-sulfanylidene)thiophene-2-carboxamide；5-methyl-N-(methyl-oxo-phenyl-lambda6-sulfanylidene)thiophene-2-carboxamide；5-methyl-N-(methyl-oxo-phenyl-λ6-sulfanylidene)thiophene-2-carboxamide
• CAS: 1616087-94-5
• 化学式: C₁₃H₁₃NO₂S₂
• 分子量: 279.384
• InChiKey: MNSJOQUAGRVHMA-UHFFFAOYSA-N

物化性质

• 熔点：
  129-131 °C
• 沸点：
  442.6±47.0 °C(predicted)
• 密度：
  1.25±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  83.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-[5-methylthenoyl]-S-methyl-S-phenylsulfoximine 、 丙烯酸乙酯 在 silver tetrafluoroborate 、 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 copper(II) acetate monohydrate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 以90%的产率得到N-[5-methyl-(E)-3-(3-ethoxy-3-oxoprop-1-en-1-yl)thenoyl]-S-methyl-S-phenylsulfoximine
  参考文献：
  名称：

  Sulfoximine-Directed Ruthenium-Catalyzed ortho-C–H Alkenylation of (Hetero)Arenes: Synthesis of EP3 Receptor Antagonist Analogue

  摘要：

  The reusable sulfoximine directing-group-assisted Ru(II)-catalyzed chemo- and regioselective ortho-C-H alkenylation of arenes and heteroarenes with acrylates and alpha,beta-unsaturated ketones/vinyl sulfone is shown. The N-aroyl sulfoximine undergoes annulation with diphenylacetylene, delivering isoquinolinones and methyl phenyl sulfoxide. The present protocol is successfully employed for the synthesis of the EP3 receptor antagonist analogue.

  DOI：

  10.1021/jo5008465
• 作为产物：
  描述：

  甲基苯基亚砜 在 4-二甲氨基吡啶 、 sodium azide 、 硫酸 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 12.0h， 生成 N-[5-methylthenoyl]-S-methyl-S-phenylsulfoximine
  参考文献：
  名称：

  Sulfoximine-Directed Ruthenium-Catalyzed ortho-C–H Alkenylation of (Hetero)Arenes: Synthesis of EP3 Receptor Antagonist Analogue

  摘要：

  The reusable sulfoximine directing-group-assisted Ru(II)-catalyzed chemo- and regioselective ortho-C-H alkenylation of arenes and heteroarenes with acrylates and alpha,beta-unsaturated ketones/vinyl sulfone is shown. The N-aroyl sulfoximine undergoes annulation with diphenylacetylene, delivering isoquinolinones and methyl phenyl sulfoxide. The present protocol is successfully employed for the synthesis of the EP3 receptor antagonist analogue.

  DOI：

  10.1021/jo5008465

文献信息

• Ruthenium-Catalyzed <i>ortho</i>-C–H Mono- and Di-imidation of Arenes with <i>N</i>-Tosyloxyphthalimide
  作者：M. Ramu Yadav、Majji Shankar、E. Ramesh、Koushik Ghosh、Akhila K. Sahoo

  DOI：10.1021/acs.orglett.5b00570

  日期：2015.4.17

  The Ru(II)-catalyzed imidation of the o-C–H bond in arenes with N-tosyloxyphthalimide is realized with the assistance of a methyl phenylsulfoximine (MPS) directing group. This method is applicable to access the hitherto difficult o-C–H di-imidation products. The sequential C–N and C–C bond formation of o-C–H arenes creates peripherally decorated benzoic acid derivatives. The readily removable MPS-DG

  N-甲苯磺酰氧基邻苯二甲酰亚胺在Ru（II）催化的芳烃中o -C-H键的酰亚胺化反应是通过甲基苯基亚磺酰亚胺（MPS）导向基团实现的。此方法适用于访问迄今困难的o -C–H二酰亚胺化产品。o -C–H芳烃的顺序C–N和C–C键形成会产生周边装饰的苯甲酸衍生物。易于除去的MPS-DG和易于修饰的邻苯二甲酰部分使该策略对于构建高度官能化的带有CN的芳烃和杂芳烃具有可行性。
• Ru-Catalyzed One-Pot Diannulation of Heteroaryls: Direct Access to π-Conjugated Polycyclic Amides
  作者：Majji Shankar、Koushik Ghosh、Kallol Mukherjee、Raja K. Rit、Akhila K. Sahoo

  DOI：10.1021/acs.orglett.6b03314

  日期：2016.12.16

  A novel Ru-catalyzed oxidative double annulation of heteroarenes with symmetrical and unsymmetrical alkynes is reported. A general method for the unsymmetrical annulation of heteroarenes with two distinct alkynes is showcased for the first time. Methylphenyl sulfoximine (MPS) plays an important role in the annulations of heteroarenes and allows the construction of structurally complex π-conjugated

  报道了具有对称和不对称炔烃的新型Ru催化的杂芳烃的氧化双环。首次展示了使用两个不同的炔烃进行杂芳烃不对称环氧化的一般方法。甲基苯基亚砜亚胺（MPS）在杂芳烃的环空中起重要作用，并允许通过一次操作形成多个C-C和C-N键来构建结构复杂的π-共轭杂芳烃稠合的多环酰胺骨架。该反应表现出优异的底物范围，并能耐受各种官能团。
• An Orchestrated Unsymmetrical Annulation Episode of C(sp²)–H Bonds with Alkynes and Quinones: Access to Spiro-isoquinolones
  作者：Kallol Mukherjee、Majji Shankar、Koushik Ghosh、Akhila K. Sahoo

  DOI：10.1021/acs.orglett.8b00468

  日期：2018.4.6

  A nontrivial Ru-catalyzed one-pot sequential oxidative coupling of a (hetero)arene/vinylic/chromene system with alkyne and quinone is presented; the methyl phenyl sulfoximine (MPS) directing group is vital. This cyclization forms four (two C–C and two C–N) bonds in a single operation and produces unusual spiro-fused-isoquinolones with a broad scope. The release of phenyl methyl sulfoxide makes the

  提出了一个非平凡的Ru催化的（杂）芳烃/乙烯基/色烯体系与炔烃和醌的一锅顺序氧化偶联；甲基苯基亚砜亚胺（MPS）导向基团至关重要。这种环化在一次操作中形成四个键（两个C–C和两个C–N），并产生了范围广泛的不寻常的螺-稠合-异喹诺酮。苯基甲基亚砜的释放使MPS基团可转化。氘加扰研究为反应路径提供了线索。
• Palladium catalyzed aroylation of NH-sulfoximines with aryl halides using chloroform as the CO precursor
  作者：Sheng-rong Guo、Pailla Santhosh Kumar、Yan-qin Yuan、Ming-hua Yang

  DOI：10.1016/j.tetlet.2017.05.088

  日期：2017.7

  A palladium-catalyzed aroylation of NH-sulfoximines for the efficient synthesis of N-aroyl sulfoximines from aryl halides and chloroform has been developed. The mild reaction conditions (temperature, catalyst loading) and the use of a CO surrogate render this transformation a useful method for the synthesis of N-aroyl sulfoximines from available feedstock.

  已经开发了钯催化的NH-亚磺酰亚胺的芳基化反应，用于从芳基卤化物和氯仿中有效合成N-芳酰基亚磺酰亚胺。温和的反应条件（温度，催化剂负载量）和使用CO替代物使该转化成为从可用原料合成N-芳酰基亚砜亚胺的有用方法。