1-Butylsulfanyl-2-phenyl-ethaneselone | 152554-82-0

• 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-Butylsulfanyl-2-phenyl-ethaneselone
• 英文别名: 1-Butylsulfanyl-2-phenylethaneselone
• CAS: 152554-82-0
• 化学式: C₁₂H₁₆SSe
• 分子量: 271.285
• InChiKey: LFAKYDGBCFRCFD-UHFFFAOYSA-N

物化性质

• 沸点：
  355.4±35.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.06
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-Butylsulfanyl-2-phenyl-ethaneselone 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 ethaneselenoic acid Se-(1-(butylthio)-2-phenyl-1-ethenyl) ester
  参考文献：
  名称：

  Ammonium Eneselenolates:  Stereochemistry and Electronic Properties

  摘要：

  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.

  DOI：

  10.1021/jo015899x
• 作为产物：
  描述：

  丁硫醇 、 Se-Phenylethynyl selenoacetate 在 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以55%的产率得到1-Butylsulfanyl-2-phenyl-ethaneselone
  参考文献：
  名称：

  Selenothioic AcidS-Esters：合成、表征和稳定性趋势

  摘要：

  硒硫代酸 S-烷基酯是由末端乙炔与正丁基锂、硒和链烷硫醇以中等至高产率反应合成的。使用取代的苯硫醇或（三苯基甲硅烷基）乙炔可以分离 S-芳基酯。α-芳基硒代硫代酸S-烷基酯的合成是通过硒代乙酸硒-炔基酯与硫醇的酸催化反应以良好的收率合成的。77Se NMR 研究表明，一系列酯的化学位移比硒酯低约 500 ppm，比硒酮高约 600 ppm。在可见光谱中，在约 340 和 568 nm 处观察到酯的吸收。α-甲硅烷基酯的 X 射线分子结构分析表明，硒羰基中的键距分别为 1.792 和 1。分别为 785 A。S-苯基酯的分解产物证实了1,3-二硒烷的形成。硒代硫酸稳定性的趋势...

  DOI：

  10.1021/ja970462l

文献信息

• Highly Efficient Generation of Ammonium Eneselenolates, Their Reactions and Electronic Properties
  作者：Toshiaki Murai、Shuuya Hayakawa、Shinzi Kato

  DOI：10.1246/cl.2000.368

  日期：2000.4

  The ammonium eneselenolates generated from selenothioic acid S-esters and ammonium fluoride were reacted with carbon electrophiles to furnish ketene selenothioacetals with high stereoselectivities. The spectroscopic properties of the ammonium eneselenolates have suggested that the electrons on the selenium atom efficiently delocalize on the carbon-carbon double bond.

  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。
• One-Pot Synthesis of Selenothioic Acid<i>S</i>-Alkyl Esters by the Reaction of Lithium Alkyneselenolates with Thiols
  作者：Toshiaki Murai、Akihiro Hayashi、Takahiro Kanda、Shinzi Kato

  DOI：10.1246/cl.1993.1469

  日期：1993.9

  The reaction of lithium alkyneselenolates generated from lithium alkynides and selenium powder with a variety of thiols afforded selenothioic acid S-alkyl esters in moderate to high yields. The product yields were highly dependent on the substituents of the starting acetylenes. The formation of unstable S-aryl ester was confirmed by the enolization followed by alkylation.

  由炔化物锂和硒粉产生的炔烃基烯醇锂与各种硫醇反应，以中等至高产率得到硒硫代酸 S-烷基酯。产物产率高度依赖于起始乙炔的取代基。通过烯醇化和烷基化证实了不稳定的 S-芳基酯的形成。
• Cadmium Acetate Mediated Cenversion of Selenothioic Acid<i>S</i>-Alkyl Esters to Selenophenes and Ketene Selenothioacetals
  作者：Toshiaki Murai、Makiko Fujii、Takahiro Kanda、Shinzi Kato

  DOI：10.1246/cl.1996.877

  日期：1996.10

  Selenothioic acid S-alkyl esters were treated with Et3N and Cd(OAc)2·2H2O to give symmetrically substituted selenophenes, whereas the similar reaction in the presence of alkyl halides afforded ketene selenothioacetals in moderate yields.

  硒硫酸S-烷基酯与Et3N和Cd(OAc)2·2H2O反应生成了对称取代的硒吡啶，而在烷基卤化物存在下进行类似反应则在中等产率下获得了烯酮硒硫醇醚。
• Murai, Toshiaki; Hayakawa, Shuuya; Miyazaki, Youhei, Phosphorus, Sulfur and Silicon and the Related Elements, 2001, vol. 171-172, p. 111 - 118
  作者：Murai, Toshiaki、Hayakawa, Shuuya、Miyazaki, Youhei、Kato, Shinzi

  DOI：——

  日期：——
• Murai, Toshiaki; Mizutani, Tomoyoshi; Ogino, Yuji, Phosphorus, Sulfur and Silicon and the Related Elements, 1998, vol. 136, p. 561 - 564
  作者：Murai, Toshiaki、Mizutani, Tomoyoshi、Ogino, Yuji、Fujiwara, Yoshinori、Kato, Shinzi

  DOI：——

  日期：——