Ethyl 2-(2-butylsulfanyl-2-selanylideneethyl)but-3-enoate | 269741-60-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Ethyl 2-(2-butylsulfanyl-2-selanylideneethyl)but-3-enoate
• CAS: 269741-60-8
• 化学式: C₁₂H₂₀O₂SSe
• 分子量: 307.316
• InChiKey: ALIVUMDIXIFIQB-UHFFFAOYSA-N

物化性质

• 沸点：
  370.4±52.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.57
• 重原子数：
  16
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-溴丙烯 、 Ethyl 2-(2-butylsulfanyl-2-selanylideneethyl)but-3-enoate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以45%的产率得到ethyl 3-butylsulfanylcarboselenoyl-2-ethenylhex-5-enoate
  参考文献：
  名称：

  Murai, Toshiaki; Hayakawa, Shuuya; Miyazaki, Youhei, Phosphorus, Sulfur and Silicon and the Related Elements, 2001, vol. 171-172, p. 111 - 118

  摘要：

  DOI：
• 作为产物：
  描述：

  4-溴巴豆酸乙酯 、 selenothioacetic acid S-butyl ester 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以61%的产率得到Ethyl 2-(2-butylsulfanyl-2-selanylideneethyl)but-3-enoate
  参考文献：
  名称：

  Highly Efficient Generation of Ammonium Eneselenolates, Their Reactions and Electronic Properties

  摘要：

  从硒硫酸S酯和氟化铵生成的铵盐烯硒醇盐与碳亲电试剂反应，生成了高立体选择性的酮烯硒硫醚。铵盐烯硒醇盐的光谱性质表明，硒原子上的电子能够有效地在碳-碳双键上进行去局域化。

  DOI：

  10.1246/cl.2000.368

文献信息

• Ammonium Eneselenolates:  Stereochemistry and Electronic Properties
  作者：Toshiaki Murai、Shuuya Hayakawa、Shinzi Kato

  DOI：10.1021/jo015899x

  日期：2001.11.1

  Ammonium eneselenolates were generated with high efficiency by reacting selenothioic acid S-esters with a THF solution of TBAF. The methylation of ammonium eneselenolates gave ketene selenothioacetals as stereoisomeric mixtures. The ratio of the two stereoisomers depended on the duration of the reaction before the addition of Mel. Ammonium eneselenolates were characterized by examining their H-1, C-13, and Se-77 NMR spectra, which indicated that ammonium eneselenolates were present almost exclusively as Z-isomers. These results suggested that ammonium eneselenolates are kinetically generated as stereoisomeric mixtures, and isomerization of E-isomers to Z-isomers then takes place to result in the exclusive formation of Z-isomers. During the methylation of Z-isomers of ammonium eneselenolates, the isomerization of Z-isomers to E-isomers occurs to give stereoisomeric mixtures of ketene selenothioacetals. NMR spectra of ammonium eneselenolates implied that the electrons at the selenium atom are somewhat delocalized to the carbon-carbon double bond and the carbon-selenium bond shows partial double-bond character.