1-phenyl-2-(pyridin-4-ylsulfinyl)ethan-1-one | 178620-85-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-phenyl-2-(pyridin-4-ylsulfinyl)ethan-1-one
• 英文别名: 1-Phenyl-2-pyridin-4-ylsulfinylethanone；1-phenyl-2-pyridin-4-ylsulfinylethanone
• CAS: 178620-85-4
• 化学式: C₁₃H₁₁NO₂S
• 分子量: 245.302
• InChiKey: JINFRLVNSZHHMU-UHFFFAOYSA-N

物化性质

• 熔点：
  114-118 °C (decomp)(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  476.4±25.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  66.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3-二甲基-1,3-丁二烯 、 1-phenyl-2-(pyridin-4-ylsulfinyl)ethan-1-one 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以19%的产率得到2-Benzoyl-3,6-dihydro-4,5-dimethyl-2H-thiopyran
  参考文献：
  名称：

  Formation of Thioaldehyde Intermediates by Thermolysis of Sulfoxides Bearing Some Heteroaromatics

  摘要：

  Thermal reactions of phenacyl sulfoxide bearing heterocycles, such as a 2-benzothiazolyl or N-oxypyridyl group, in the presence of 2,3-dimethyl-1,3-butadiene afforded 6-benzoyl-5,6-dihydro-3,4-dimethyl-2H-thiapyran in good yield. This product is considered to be formed by the Diels-Alder reaction of a diene with thioaldehyde formed initially by the decomposition of sulfoxides.

  DOI：

  10.1021/jo9700181
• 作为产物：
  描述：

  1-Phenyl-2-(pyridin-4-ylsulfanyl)-ethanone 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 以41%的产率得到1-phenyl-2-(pyridin-4-ylsulfinyl)ethan-1-one
  参考文献：
  名称：

  Formation of Thioaldehyde Intermediates by Thermolysis of Sulfoxides Bearing Some Heteroaromatics

  摘要：

  Thermal reactions of phenacyl sulfoxide bearing heterocycles, such as a 2-benzothiazolyl or N-oxypyridyl group, in the presence of 2,3-dimethyl-1,3-butadiene afforded 6-benzoyl-5,6-dihydro-3,4-dimethyl-2H-thiapyran in good yield. This product is considered to be formed by the Diels-Alder reaction of a diene with thioaldehyde formed initially by the decomposition of sulfoxides.

  DOI：

  10.1021/jo9700181

文献信息

• Thiapyran formation via an unexpected thioaldehyde intermediate by the thermal decomposition of phenacyl sulfoxides bearing some heterocycles
  作者：Hiroyuki Morita、Masahiro Takeda、Hideo Kamiyama、Tadaaki Hashimoto、Toshiaki Yoshimura、Choichiro Shimasaki、Eiichi Tsukurimichi

  DOI：10.1016/0040-4039(96)00673-9

  日期：1996.5

  nitrogen-containing heterocycles in the presence of 2,3-dimethyl-1,3-butadiene led to 6-benzoyl-5,6-dihydro-3,4-dimethyl-2H-thiapyran. This product was considered to be formed by the Diels-Alder reaction of the diene with thioaldehyde formed initially by the thermal decomposition of the sulfoxide.

  热解苯甲酰甲基亚砜的轴承一些含氮杂环在导致6-苯甲酰基-5,6-二氢-3,4-二甲基-2- 2,3-二甲基-1,3-丁二烯的存在ħ -thiapyran。该产物被认为是由二烯的Diels-Alder反应与最初通过亚砜的热分解而形成的硫代醛形成的。
• Tf₂O-Mediated Direct Synthesis of 4-Sulfenylated Oxazoles from β-Keto Sulfoxides and Nitriles
  作者：Jiateng Wang、Yunqing Zhuang、Bingxue Yu、Xiaofeng Wang、Gehua Bi、Xin Huang、Weimin Zhang

  DOI：10.1021/acs.joc.2c01630

  日期：2022.11.4

  A general and efficient method for the synthesis of 4-sulfenylated oxazoles is described. Trisubstituted oxazoles are obtained in good to excellent yields from β-keto sulfoxides and nitriles. The mechanistic study suggests that the reaction proceeds via the nucleophilic addition of nitriles to the in situ formed α-carbonyl cation followed by intramolecular cyclization.

  描述了一种合成 4-亚磺酰化恶唑的通用且有效的方法。由 β-酮亚砜和腈以良好至优异的产率获得三取代的恶唑。机理研究表明，反应通过将腈亲核加成原位形成的 α-羰基阳离子，然后进行分子内环化来进行。
• Formation of Thioaldehyde Intermediates by Thermolysis of Sulfoxides Bearing Some Heteroaromatics
  作者：Hiroyuki Morita、Masahiro Takeda、Takayoshi Fujii、Toshiaki Yoshimura、Choichiro Shimasaki

  DOI：10.1021/jo9700181

  日期：1997.12.1

  Thermal reactions of phenacyl sulfoxide bearing heterocycles, such as a 2-benzothiazolyl or N-oxypyridyl group, in the presence of 2,3-dimethyl-1,3-butadiene afforded 6-benzoyl-5,6-dihydro-3,4-dimethyl-2H-thiapyran in good yield. This product is considered to be formed by the Diels-Alder reaction of a diene with thioaldehyde formed initially by the decomposition of sulfoxides.