1-[Dimethyl(oxo)-lambda6-sulfanylidene]-5-phenylpentan-2-one | 1179348-64-1

• 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: 1-[Dimethyl(oxo)-lambda6-sulfanylidene]-5-phenylpentan-2-one
• 英文别名: 1-[dimethyl(oxo)-λ6-sulfanylidene]-5-phenylpentan-2-one
• CAS: 1179348-64-1
• 化学式: C₁₃H₁₈O₂S
• 分子量: 238.351
• InChiKey: ZABVQBWEWTUKMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[Dimethyl(oxo)-lambda6-sulfanylidene]-5-phenylpentan-2-one 在 bis(1,5-cyclooctadiene)diiridium(I) dichloride 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以94%的产率得到(E)-1,10-diphenyl-dec-5-ene-4,7-dione
  参考文献：
  名称：

  Iridium-Catalyzed X−H Insertions of Sulfoxonium Ylides

  摘要：

  The unique reactivity of sulfoxonium ylides as a carbene source is described for a variety of X-H bond insertions, taking advantage of a simple, commercially available iridium catalyst. This method has applications in both intra- and intermolecular reactivity, including a practical ring-expansion strategy for lactams. The safety and stability of sulfoxonium ylides recommend them as preferable surrogates to traditional diazo ketones and esters.

  DOI：

  10.1021/ol901298p
• 作为产物：
  描述：

  4-苯丁酸甲酯 、 三甲基氯化亚砜 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以72%的产率得到1-[Dimethyl(oxo)-lambda6-sulfanylidene]-5-phenylpentan-2-one
  参考文献：
  名称：

  Iridium-Catalyzed X−H Insertions of Sulfoxonium Ylides

  摘要：

  The unique reactivity of sulfoxonium ylides as a carbene source is described for a variety of X-H bond insertions, taking advantage of a simple, commercially available iridium catalyst. This method has applications in both intra- and intermolecular reactivity, including a practical ring-expansion strategy for lactams. The safety and stability of sulfoxonium ylides recommend them as preferable surrogates to traditional diazo ketones and esters.

  DOI：

  10.1021/ol901298p

文献信息

• Electrochemical Stereoselective Synthesis of Polysubstituted 1,4-dicarbonyl Z-Alkenes via Three-Component Coupling of Sulfoxonium Ylides, Alkynes with Water
  作者：Hao-Ran Li、Yi-An Ran、Yu-Yi Zhu、Weisi Guo、Shao-Fei Ni、Li-Rong Wen、Ming Li、Lin-Bao Zhang

  DOI：10.1039/d4sc01141d

  日期：——

  The first straightforward strategy for the synthesis of 1,4-dicarbonyl Z-alkenes has been developed via an electrochemical cross-coupling reaction of sulfoxonium ylides and alkynes with water. The metal-free protocol showed an easy-to-handle nature, good functional group tolerance, and high Z-stereoselectivity, which is rare in previous cases. The proposed reaction mechanism was convincingly established

  合成 1,4-二羰基Z-烯烃的第一个直接策略是通过亚砜叶立德和炔烃与水的电化学交叉偶联反应开发的。无金属方案表现出易于处理的性质、良好的官能团耐受性和高Z-立体选择性，这在以前的案例中是罕见的。通过进行一系列控制实验、循环伏安实验和密度泛函理论（DFT）研究，令人信服地建立了所提出的反应机理。
• Iridium-Catalyzed X−H Insertions of Sulfoxonium Ylides
  作者：Ian K. Mangion、Ikenna K. Nwamba、Michael Shevlin、Mark A. Huffman

  DOI：10.1021/ol901298p

  日期：2009.8.20

  The unique reactivity of sulfoxonium ylides as a carbene source is described for a variety of X-H bond insertions, taking advantage of a simple, commercially available iridium catalyst. This method has applications in both intra- and intermolecular reactivity, including a practical ring-expansion strategy for lactams. The safety and stability of sulfoxonium ylides recommend them as preferable surrogates to traditional diazo ketones and esters.