1-Butylsulfanyl-3-methylpent-4-ene-1-selone | 173281-74-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫基化合物
• 英文名称: 1-Butylsulfanyl-3-methylpent-4-ene-1-selone
• CAS: 173281-74-8
• 化学式: C₁₀H₁₈SSe
• 分子量: 249.279
• InChiKey: LQNHHLPWMQVEJD-UHFFFAOYSA-N

物化性质

• 沸点：
  287.8±33.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.03
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 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-3-methylpent-4-ene-1-selone 以 四氢呋喃 为溶剂， 反应 0.02h， 生成 benzenecarboselenoic acid Se-(1-(butylthio)-3-methyl-1,4-pentadienyl) 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：

  2-丁烯基溴 、 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73%的产率得到1-Butylsulfanyl-3-methylpent-4-ene-1-selone
  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

• 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。
• 4-Penteneselenothioic acid S-alkyl esters: Synthesis via the seleno-Claisen rearrangement
  作者：Toshiaki Murai、Hiroya Takada、Kaori Kakami、Makiko Fujii、Masahiko Maeda、Shinzi Kato

  DOI：10.1016/s0040-4020(97)00556-5

  日期：1997.8

  Selenothioic acid S-alkyl esters were reacted with allylic bromides in the presence of Et3N. Mono-, di- or tri-allylatd products were selectively formed by changing reaction temperatures, times and allylic bromides used. The reaction proceeded with high regio- and stereoselectivity via the seleno-Claisen rearrangement. The selective synthesis of monoallylated esters was also attained by the reaction

  在Et 3 N存在下，使硒代硫代酸S-烷基酯与烯丙基溴反应。通过改变反应温度，时间和所用的烯丙基溴选择性地形成单，二或三烯丙基的产物。该反应通过seleno-Claisen重排以高度的区域选择性和立体选择性进行。还可以通过原位生成的烯醇硒酸锂与烯丙基溴的反应来实现单烯丙基化酯的选择性合成。
• Selective Allylations of Selenothioic Acid<i>S</i>-Alkyl Esters with Allylic Bromides
  作者：Toshiaki Murai、Hiroya Takada、Takahiro Kanda、Shinzi Kato

  DOI：10.1246/cl.1995.1057

  日期：1995.11

  Allylations of selenothioic acid S-alkyl esters with allylic bromides in the presence of Et3N in THF took place selectively at the α-position of selenocarbonyl group to give allylated products with high regio- and stereo-selectivity.

  在THF中，三乙胺的存在下，硒硫酸S-烷基酯与烯丙基溴化物的烯丙基化反应选择性地发生在硒羰基的α位，生成具有高区域选择性和立体选择性的烯丙基化产物。
• 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：——
• 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.