2-pyridyl phenacyl sulfoxide | 178620-84-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-pyridyl phenacyl sulfoxide
• 英文别名: 1-Phenyl-2-pyridin-2-ylsulfinylethanone
• CAS: 178620-84-3
• 化学式: C₁₃H₁₁NO₂S
• 分子量: 245.302
• InChiKey: UWWACNRNBHZFRD-UHFFFAOYSA-N

物化性质

• 熔点：
  92 °C(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)：
  1.8
• 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 、 2-pyridyl phenacyl sulfoxide 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以10%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-2-ylthio)ethan-1-one 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 以66%的产率得到2-pyridyl phenacyl sulfoxide
  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。
• Hajipour; Mohammadpoor Baltork; Kianfar, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999, vol. 38, # 5, p. 607 - 610
  作者：Hajipour、Mohammadpoor Baltork、Kianfar

  DOI：——

  日期：——
• 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.