(E)-ethanethial S-oxide | 32157-30-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代羰基化合物
• 英文名称: (E)-ethanethial S-oxide
• 英文别名: (Z)-ethanethial S-oxide；Z-Ethanethial S-oxide；Ethanethial-S-oxide；ethanethial S-oxide；thioacetaldehyde S-oxide；sulfinylethane；(Oxo-lambda~4~-sulfanylidene)ethane；1-sulfinylethane
• CAS: 32157-30-5；70565-75-2；74635-28-2
• 化学式: C₂H₄OS
• 分子量: 76.1192
• InChiKey: KUGFGBASDDWLNF-UHFFFAOYSA-N

物化性质

• 沸点：
  74.2±23.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  4
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  18.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-ethanethial S-oxide 在 氯化亚砜 作用下， 以 一氟三氯甲烷 为溶剂， 以52%的产率得到di-α-chloroethyldisulfide
  参考文献：
  名称：

  硫化物的化学。9.α-氯烷基链烷硫磺酸酯的新颖合成

  摘要：

  硫与亚磺酰氯反应生成α-氯烷基链烷硫基磺酸酯，与亚硫酰氯反应生成α-氯链烷磺基氯化物，两者均收率良好。

  DOI：

  10.1016/s0040-4039(00)85656-7
• 作为产物：
  描述：

  ethanesulfinyl chloride 在 三乙胺 作用下， 以 一氟三氯甲烷 为溶剂， 生成 (E)-ethanethial S-oxide
  参考文献：
  名称：

  Allium Chemistry:  Microwave Spectroscopic Identification, Mechanism of Formation, Synthesis, and Reactions of (E,Z)-Propanethial S-Oxide, the Lachrymatory Factor of the Onion (Allium cepa)

  摘要：

  Flow pyrolysis of 2-methyl-2-propyl 1'-propenyl sulfoxide (9b) affords a 98:2 mixture of (Z)- and (E)-propanethial S-oxide ((Z)- and (E)-5b), both characterized by Fourier transform microwave (FT-MW) spectroscopy, Sulfines (Z)- and (E)-5b are also identified by FT-MW in chopped onion volatiles and by NMR spectroscopy in onion extracts. Similarly, flow pyrolysis of 2-methyl-2-propyl vinyl sulfoxide (9c) affords (Z)- and (E)-isomers of ethanethial S-oxide (5a), identified by FT-MW methods. Pyrolysis in the presence of D2O affords (Z)-5a-d(1) and (Z)-5a-d(2) from 99 and (Z)-5b-d(1) from 9b; (Z)-5b-d(1) is also produced when an onion is homogenized in D2O. Pyrolysis of 9c with ethyl propiolate gives ethyl (E)-3-(vinylsulfinyl)acrylate (10). Neat 59 at 100 degrees C gives acetaldehyde. On standing, 5b dimerizes to trans-3,3-diethyl-1,2-dithietane 1,1-dioxide (12a); Me(3)SiCH=S+-O- (5f) undergoes an analogous dimerization. Compound 5b shows moderate potency as an anticarcinogen in inducing the enzyme quinone reductase.

  DOI：

  10.1021/ja960722j

文献信息

• The chemistry of sulfines. 10. 2-Thiabicyclo[2.2.1]hept-5-ene endo-2-oxide derivatives: stereospecific formation, rearrangement to bicyclic sultenes, and conversion to 5-alkylidene-2-cyclopentenones
  作者：Eric Block、Alan Wall、Jon Zubieta

  DOI：10.1021/ja00292a066

  日期：1985.3
• BLOCK, E.;WALL, A.;ZUBIETA, J., J. AMER. CHEM. SOC., 1985, 107, N 6, 1783-1784
  作者：BLOCK, E.、WALL, A.、ZUBIETA, J.

  DOI：——

  日期：——
• <i>Allium</i> Chemistry:  Microwave Spectroscopic Identification, Mechanism of Formation, Synthesis, and Reactions of (<i>E</i>,<i>Z</i>)-Propanethial <i>S</i>-Oxide, the Lachrymatory Factor of the Onion (<i>Allium cepa</i>)
  作者：Eric Block、Jennifer Z. Gillies、Charles W. Gillies、Ali A. Bazzi、David Putman、Larry K. Revelle、Dongyi Wang、Xing Zhang

  DOI：10.1021/ja960722j

  日期：1996.1.1

  Flow pyrolysis of 2-methyl-2-propyl 1'-propenyl sulfoxide (9b) affords a 98:2 mixture of (Z)- and (E)-propanethial S-oxide ((Z)- and (E)-5b), both characterized by Fourier transform microwave (FT-MW) spectroscopy, Sulfines (Z)- and (E)-5b are also identified by FT-MW in chopped onion volatiles and by NMR spectroscopy in onion extracts. Similarly, flow pyrolysis of 2-methyl-2-propyl vinyl sulfoxide (9c) affords (Z)- and (E)-isomers of ethanethial S-oxide (5a), identified by FT-MW methods. Pyrolysis in the presence of D2O affords (Z)-5a-d(1) and (Z)-5a-d(2) from 99 and (Z)-5b-d(1) from 9b; (Z)-5b-d(1) is also produced when an onion is homogenized in D2O. Pyrolysis of 9c with ethyl propiolate gives ethyl (E)-3-(vinylsulfinyl)acrylate (10). Neat 59 at 100 degrees C gives acetaldehyde. On standing, 5b dimerizes to trans-3,3-diethyl-1,2-dithietane 1,1-dioxide (12a); Me(3)SiCH=S+-O- (5f) undergoes an analogous dimerization. Compound 5b shows moderate potency as an anticarcinogen in inducing the enzyme quinone reductase.
• The chemistry of sulfines. 9. A novel synthesis of α-chloroalkyl alkanethiosulfonate esters
  作者：Eric Block、Ali A. Bazzi

  DOI：10.1016/s0040-4039(00)85656-7

  日期：1982.1

  Sulfines react with sulfinyl chlorides giving α-chloroalkyl alkanethiosulfonate esters and with thionyl chloride giving α-chloroalkanesulfenyl chlorides, both in good yields.

  硫与亚磺酰氯反应生成α-氯烷基链烷硫基磺酸酯，与亚硫酰氯反应生成α-氯链烷磺基氯化物，两者均收率良好。

表征谱图