2-((4-hydroxyphenyl)thio)-1-phenylethan-1-one | 129691-54-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-((4-hydroxyphenyl)thio)-1-phenylethan-1-one
• 英文别名: 2-(4-Hydroxyphenyl)sulfanyl-1-phenylethanone
• CAS: 129691-54-9
• 化学式: C₁₄H₁₂O₂S
• 分子量: 244.314
• InChiKey: YUTSEMQWRHUKQB-UHFFFAOYSA-N

物化性质

• 沸点：
  428.7±30.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  叔丁基二甲基氯硅烷 、 2-((4-hydroxyphenyl)thio)-1-phenylethan-1-one 生成 2-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-ethanol
  参考文献：
  名称：

  Wang p -alkoxyphenylsulfoxide as a new linker and Pummerer cleavage strategy in solid-phase preparation of 1,2-diols

  摘要：

  para-Hydroxyphenyl-beta -ketosulfide was attached to a Wang resin and oxidised to the corresponding sulfoxide with a N-protonated oxaziridinium trifluoroacetate. Reduction of the beta -ketosulfoxides to the corresponding beta -hydroxysulfoxides with Dibal-H was shown to be as stereoselective as in solution. Finally it was shown that the Pummerer reaction could be carried out on solid-phase and was a very efficient way to obtain diols that validates the sulfoxide group as a versatile linker for solid-phase chemistry. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01557-x
• 作为产物：
  描述：

  苯甲酰氯 在 potassium tert-butylate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 29.0h， 生成 2-((4-hydroxyphenyl)thio)-1-phenylethan-1-one
  参考文献：
  名称：

  铱催化的磺化ulf盐类胡萝卜素插入物在水中合成喹喔啉和β-酮基硫醚

  摘要：

  这项工作证明了通过关键的N–H插入，利用sulf基亚砜作为安全的卡宾来源制备喹喔啉的有效和绿色合成策略。该方法还适用于在温和且经济的条件下合成β-酮硫醚的S–H插入物。该策略避免了重氮化合物的安全性问题和有机溶剂的使用，从而满足了可持续化学的要求。

  DOI：

  10.1002/ejoc.202000716

文献信息

• Iridium-Catalyzed Carbenoid Insertion of Sulfoxonium Ylides for Synthesis of Quinoxalines and β-Keto Thioethers in Water
  作者：Yingying Xu、Xin Huang、Guanghui Lv、Ruizhi Lai、Songyang Lv、Jianglian Li、Li Hai、Yong Wu

  DOI：10.1002/ejoc.202000716

  日期：2020.8.9

  This work demonstrates an effective and green synthetic strategy for the preparation of quinoxalines utilizing sulfoxonium ylides as safe carbene sources via a key N–H insertion. The method was also applied to S–H insertions for synthesis of β‐keto thioethers under mild and economical conditions. This strategy avoids the safety issues of diazo compounds and the use of organic solvents, which meets

  这项工作证明了通过关键的N–H插入，利用sulf基亚砜作为安全的卡宾来源制备喹喔啉的有效和绿色合成策略。该方法还适用于在温和且经济的条件下合成β-酮硫醚的S–H插入物。该策略避免了重氮化合物的安全性问题和有机溶剂的使用，从而满足了可持续化学的要求。
• Wang p -alkoxyphenylsulfoxide as a new linker and Pummerer cleavage strategy in solid-phase preparation of 1,2-diols
  作者：Catherine Rolland、Gilles Hanquet、Jean-Bernard Ducep、Guy Solladié

  DOI：10.1016/s0040-4039(01)01557-x

  日期：2001.10

  para-Hydroxyphenyl-beta -ketosulfide was attached to a Wang resin and oxidised to the corresponding sulfoxide with a N-protonated oxaziridinium trifluoroacetate. Reduction of the beta -ketosulfoxides to the corresponding beta -hydroxysulfoxides with Dibal-H was shown to be as stereoselective as in solution. Finally it was shown that the Pummerer reaction could be carried out on solid-phase and was a very efficient way to obtain diols that validates the sulfoxide group as a versatile linker for solid-phase chemistry. (C) 2001 Elsevier Science Ltd. All rights reserved.