N,N-diethyl-2-(phenylthio)prop-2-en-1-amine

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: N,N-diethyl-2-(phenylthio)prop-2-en-1-amine
• 英文别名: N,N-diethyl-2-phenylsulfanylprop-2-en-1-amine
• 化学式: C₁₃H₁₉NS
• 分子量: 221.367
• InChiKey: PPXYCHXHWJLFQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  28.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  isopropenyl phenyl sulfide 在 sodium periodate 、 乙基溴化镁 、 二乙胺 作用下， 反应 1.0h， 生成 N,N-diethyl-2-(phenylthio)prop-2-en-1-amine
  参考文献：
  名称：

  Reactions of Vinyl Sulfoxides with Magnesium Amides. One-Pot Synthesis of Symmetrical and Unsymmetrical β-(Dialkylamino) Dithioacetals

  摘要：

  Vinyl sulfoxides (PhSOCR1=CHR2: R-1 = H, Me, or Ph; R-2 = H Or Me) were treated with (dialkylamino)magnesium reagents, generated in situ from the reaction of EtMgBr with secondary amines ((RRNH)-R-3-N-4: R-3 = Et, i-Pr, or Bn; R-4 = Me, Et, or i-Pr) in refluxing Et2O for 1 h, and stirring at room-temperature overnight gave the corresponding symmetrical beta-(dialkylamino) dithioacetals [(PhS)(2)(CRCHRNRR4)-C-1-N-2-R-3] in 24-84% yields. When the (diethylamino)magnesium reagent was treated with appropriate thiols (RSH; R = p-ClC6H4 or Bn) prior to the interaction with phenyl vinyl sulfoxide, the corresponding unsymmetrical beta-(diethylamino) dithioacetals [(PhS)(RS)CHCH2NEt2] were produced in 63-67% yields.

  DOI：

  10.1021/jo970741r

文献信息

• Regioselective Markovnikov Hydrochalcogenation of Terminal Alkynes with Indium(III) Benzenechalcogenolates
  作者：Clovis Peppe、Liérson Borges de Castro、Melina de Azevedo Mello、Olga Soares do Rego Barros

  DOI：10.1055/s-2008-1072725

  日期：2008.5

  Indium(III) benzenechalcogenolates (chalcogen = sulfur and selenium) promote the rigorous Markovnikov hydrochalcogenation of terminal alkynes. The generality and limitations of the reaction with aminoalkynes leading to allylic amines bearing vinylic chalcogenide substituents are discussed.

  铟 (III) 苯硫属元素化物（硫属元素 = 硫和硒）促进末端炔烃的严格马尔科夫尼科夫加氢硫属元素化。讨论了与氨基炔烃反应生成带有乙烯基硫属化物取代基的烯丙胺的反应的一般性和局限性。
• Reactions of Vinyl Sulfoxides with Magnesium Amides. One-Pot Synthesis of Symmetrical and Unsymmetrical β-(Dialkylamino) Dithioacetals
  作者：Masataka Kawakita、Kouichi Yokota、Hideki Akamatsu、Susumu Irisawa、Osamu Morikawa、Hisatoshi Konishi、Kazuhiro Kobayashi

  DOI：10.1021/jo970741r

  日期：1997.11.1

  Vinyl sulfoxides (PhSOCR1=CHR2: R-1 = H, Me, or Ph; R-2 = H Or Me) were treated with (dialkylamino)magnesium reagents, generated in situ from the reaction of EtMgBr with secondary amines ((RRNH)-R-3-N-4: R-3 = Et, i-Pr, or Bn; R-4 = Me, Et, or i-Pr) in refluxing Et2O for 1 h, and stirring at room-temperature overnight gave the corresponding symmetrical beta-(dialkylamino) dithioacetals [(PhS)(2)(CRCHRNRR4)-C-1-N-2-R-3] in 24-84% yields. When the (diethylamino)magnesium reagent was treated with appropriate thiols (RSH; R = p-ClC6H4 or Bn) prior to the interaction with phenyl vinyl sulfoxide, the corresponding unsymmetrical beta-(diethylamino) dithioacetals [(PhS)(RS)CHCH2NEt2] were produced in 63-67% yields.