N-[2-(vinyloxy)ethyl]-3-butenethioamide | 827320-18-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代酰胺
• 英文名称: N-[2-(vinyloxy)ethyl]-3-butenethioamide
• 英文别名: 3-Butenethioamide, N-[2-(ethenyloxy)ethyl]-；N-(2-ethenoxyethyl)but-3-enethioamide
• CAS: 827320-18-3
• 化学式: C₈H₁₃NOS
• 分子量: 171.263
• InChiKey: OSMLKRRWEBHFAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  53.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-[2-(vinyloxy)ethyl]-3-butenethioamide 在 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 反应 3.0h， 以82%的产率得到N-[2-(vinyloxy)ethyl]-2-butenethioamide
  参考文献：
  名称：

  Reactions of Heterocumulenes with Organometallic Reagents: IX. Synthesis and Rearrangements of N-Allyl-and N-[2-(Vinyloxy)ethyl]-3-butenethioamides and -1-(methylsulfanyl)-3-buten-1-imines

  摘要：

  Reactions of allyl and 2-(vinyloxy)ethyl isothiocyanates with alyylmagnesium bromide (THF-Et2O, 20-30degreesC, 1-3 h) after hydrolysis or alkylation of adducts afforded respectively N-allyl- and N-[2-(vinyloxy)ethyl]3-butenethioamides or N-allyl- and N-[2-(vinyloxy)ethyl]-1-(methylmercapto)-3-buten-1-imines The reaction carried out in ethyl ether yielded instead of N-allyl-3-butenethioamide its isomer N-allyl-2-butenethioamide that cleanly isomerized in the system KOH-DMSO-H2O into N-(I-propenyl)-2-butenethioamide. N-[2-(vinyloxy)ethyl]-3-butenethioamide suffers a prototropic rearrangement into N-[2-(vinyloxy)ethyl]-2-butenethioamide only in the system t-BuOK-DMSO.

  DOI：

  10.1023/b:rujo.0000034938.57063.55
• 作为产物：
  描述：

  2-(vinyloxy)ethyl isothiocyanate 、 烯丙基溴化镁 以 四氢呋喃 、 乙醚 为溶剂， 反应 1.5h， 以90%的产率得到N-[2-(vinyloxy)ethyl]-3-butenethioamide
  参考文献：
  名称：

  Reactions of Heterocumulenes with Organometallic Reagents: IX. Synthesis and Rearrangements of N-Allyl-and N-[2-(Vinyloxy)ethyl]-3-butenethioamides and -1-(methylsulfanyl)-3-buten-1-imines

  摘要：

  Reactions of allyl and 2-(vinyloxy)ethyl isothiocyanates with alyylmagnesium bromide (THF-Et2O, 20-30degreesC, 1-3 h) after hydrolysis or alkylation of adducts afforded respectively N-allyl- and N-[2-(vinyloxy)ethyl]3-butenethioamides or N-allyl- and N-[2-(vinyloxy)ethyl]-1-(methylmercapto)-3-buten-1-imines The reaction carried out in ethyl ether yielded instead of N-allyl-3-butenethioamide its isomer N-allyl-2-butenethioamide that cleanly isomerized in the system KOH-DMSO-H2O into N-(I-propenyl)-2-butenethioamide. N-[2-(vinyloxy)ethyl]-3-butenethioamide suffers a prototropic rearrangement into N-[2-(vinyloxy)ethyl]-2-butenethioamide only in the system t-BuOK-DMSO.

  DOI：

  10.1023/b:rujo.0000034938.57063.55

文献信息

• Reactions of Heterocumulenes with Organometallic Reagents: IX. Synthesis and Rearrangements of N-Allyl-and N-[2-(Vinyloxy)ethyl]-3-butenethioamides and -1-(methylsulfanyl)-3-buten-1-imines
  作者：L. L. Dmitrieva、L. P. Nikitina、A. I. Albanov、G. I. Sarapulova、N. A. Nedolya、L. Brandsma

  DOI：10.1023/b:rujo.0000034938.57063.55

  日期：2004.2

  Reactions of allyl and 2-(vinyloxy)ethyl isothiocyanates with alyylmagnesium bromide (THF-Et2O, 20-30degreesC, 1-3 h) after hydrolysis or alkylation of adducts afforded respectively N-allyl- and N-[2-(vinyloxy)ethyl]3-butenethioamides or N-allyl- and N-[2-(vinyloxy)ethyl]-1-(methylmercapto)-3-buten-1-imines The reaction carried out in ethyl ether yielded instead of N-allyl-3-butenethioamide its isomer N-allyl-2-butenethioamide that cleanly isomerized in the system KOH-DMSO-H2O into N-(I-propenyl)-2-butenethioamide. N-[2-(vinyloxy)ethyl]-3-butenethioamide suffers a prototropic rearrangement into N-[2-(vinyloxy)ethyl]-2-butenethioamide only in the system t-BuOK-DMSO.