Methyl (E,Z)-1-propenyl sulfide | 10152-77-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: Methyl (E,Z)-1-propenyl sulfide
• 英文别名: methyl prop-1-enyl sulphide；methyl 1-propenyl sulfide；methyl-1-propenyl sulfide；1-(methylthio)-1-propene；propenyl methyl sulfide；1-methylthio-1-propene；1-Propene, 1-(methylthio)-；1-methylsulfanylprop-1-ene
• CAS: 10152-77-9
• 化学式: C₄H₈S
• 分子量: 88.1735
• InChiKey: YJOGCMRDEUBRJD-UHFFFAOYSA-N

物化性质

• 沸点：
  102.2±9.0 °C(Predicted)
• 密度：
  0.863±0.06 g/cm3(Predicted)
• LogP：
  1.56
• 物理描述：
  Clear to pale yellow liquid; Acrid strong garlic-like aroma
• 溶解度：
  Practically insoluble or insoluble in water
• 折光率：
  1.479-1.489

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  5
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  Methyl (E,Z)-1-propenyl sulfide 在 氨 、 碘 、 lithium 、 potassium iodide 作用下， 生成 bis(1-propenyl) disulfide
  参考文献：
  名称：

  Allium Chemistry:  Structure, Synthesis, Natural Occurrence in Onion (Allium cepa), and Reactions of 2,3-Dimethyl-5,6-dithiabicyclo[2.1.1]hexane S-Oxides

  摘要：

  Peracetic acid oxidation of di-1-propenyl disulfide (8) gives (+/-)-(1 alpha,2 alpha,3 beta,4 alpha,5 beta)-2,3-dimethyl-5,6-dithiabicyclo[2.1.1]hexane 5-oxide (10a; 10%) and (1 alpha,2 alpha,3 alpha,4 alpha,5 beta)-2,3-dimethyl-5,6-dithiabicyclo[2.1.1]hexane 5-oxide (11a; 11%), both also isolated from extracts of homogenized onion. Compound 10a could be converted into bissulfoxides (+/-)-(1 alpha,2 alpha,3 beta,4 alpha,5 alpha,6 alpha)-2,3-dimethyl-5,6-dithiabicylo[2.1.1]hexane 5,6-dioxide (16) and (+/-)-(1 alpha,2 alpha,3 beta,4 alpha,5 beta,6 alpha)-2,3-dimethyl-5,6-ditiabicyclo[2.1.1]hexane 5,6-dioxide (17a); these could be oxidized further to (+/-)-(1 alpha,2 alpha,3 beta,3 alpha,5 alpha,5 beta,6 alpha)-2,3-dimethyl-5,6-dithiabicyclo[2.1.1]hexane 5,5,6-trioxide (18a) and (+/-)-(1 alpha,2 alpha,3 beta,4 alpha,5 alpha,5 beta,6 beta)-2,3-dimethyl-5,6-dithiabicyclo[2.1.1]hexane 5,5,6-trioxide (18b) from 16 and 18a from 17a. Extended oxidation of 10a gave (+/-)-trans-2,3-dimethyl-5,6-dithiabicyclo[2.1.1]hexane 5,5,6,6-tetraoxide (19). Oxidation of 11a gave (1 alpha,2 alpha,3 alpha,3 alpha,5 beta,6 beta)-2,3-dimethyl-5,6-dithiabicyclo[2.1.1]hexane 5,6-dioxide (21a) which was further oxidized to trioxides (1 alpha,2 alpha,3 alpha,4 alpha,5 alpha,5 beta,6 beta)-2,3-dimethyl-5,6-dithiabicyclo[2.1.1]hexane 5,5,6-trioxide (23a) and (1 alpha,2 beta,3 beta,4 alpha,5 alpha,5 beta,6 beta)-2,3-dimethyl-5,6-dithiabicyclo[2.1.1]hexane 5,5,6-trioxide (23b) and a bissulfone (cis-2,3-dimethyl-5,6-dithiabicyclo[2.1.1]hexane 5,5,6,6-tetraoxide (24)). The structures of 18a, 19, 21a, and 23a were determined by X-ray crystallography. with the proof of the structure of 18a, structures for 17a and 10a are thereby unequivocally established.

  DOI：

  10.1021/ja951134t
• 作为产物：
  描述：

  methyl dithiopropionate 在 磷酸 、 硫酸 作用下， 生成 Methyl (E,Z)-1-propenyl sulfide
  参考文献：
  名称：

  Boonstra et al., Recueil des Travaux Chimiques des Pays-Bas, 1959, vol. 78, p. 252,263

  摘要：

  DOI：

文献信息

• Selectivity in cycloadditions—-XII
  作者：P. Caramella、T. Bandiera、P. Grünanger、F. Marinone Albini

  DOI：10.1016/s0040-4020(01)91194-9

  日期：1984.1

  Cycloadditions of nitrile oxides to 2,3-dihydrofuran are highly regioselective whereas the regioselectivity of the cycloadditions to 2,3-dihydrothiophen is only moderate. The directing effect of oxygen and sulfur in these cycloadditions could be evaluated at 2.8 and 1.1 Kcal mol-1 respectively. The related acyclic sulfur dipolarophiles, (E)-propenyl methyl and phenyl sulfides, similarly undergo cycloadditions

  腈氧化物对2，3-二氢呋喃的环加成反应具有很高的区域选择性，而对2，3-二氢噻吩的环加成反应的区域选择性仅适中。在这些环加成反应中，氧和硫的定向作用可以分别在2.8和1.1 Kcal mol -1下评估。相关的无环硫双极性亲和剂（（E）-丙烯基甲基和苯基硫化物）同样以中等区域化学方式进行环加成反应。
• Bandmann, Heinz; Bartik, Tamas; Bauckloh, Sylvia, Zeitschrift fur Chemie, 1990, vol. 30, # 6, p. 193 - 204
  作者：Bandmann, Heinz、Bartik, Tamas、Bauckloh, Sylvia、Behler, Ansgar、Brille, Frank、et al.

  DOI：——

  日期：——
• Onion essential oil chemistry. Cis-and trans-2-mercapto-3,4-dimethyl 2,3-dihydrothiophene from pyrolysis of bis(1-propenyl) disulfide
  作者：Eric Block、Hai Zhao Shu

  DOI：10.1016/s0040-4039(00)97788-8

  日期：1990.1
• Mannich; Fresenius, Archiv der Pharmazie, 1936, p. 467,469
  作者：Mannich、Fresenius

  DOI：——

  日期：——
• Svata,V. et al., Collection of Czechoslovak Chemical Communications, 1978, vol. 43, p. 2619 - 2634
  作者：Svata,V. et al.

  DOI：——

  日期：——