trans-3,4-diethyl-1,2-dithietane 1,1-dioxide | 74045-82-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二硫杂环丁烷
• 英文名称: trans-3,4-diethyl-1,2-dithietane 1,1-dioxide
• 英文别名: (3R,4R)-3,4-diethyldithietane 1,1-dioxide
• CAS: 74045-82-2
• 化学式: C₆H₁₂O₂S₂
• 分子量: 180.292
• InChiKey: SDTZZDFOMMWFSN-PHDIDXHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  67.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  trans-3,4-diethyl-1,2-dithietane 1,1-dioxide 在 lithium aluminium tetrahydride 作用下， 生成 dl-hexane-3,4-thiol
  参考文献：
  名称：

  The chemistry of sulfines. 6. Dimer of the onion lachrymatory factor: the first stable 1,2-dithietane derivative

  摘要：

  DOI：

  10.1021/ja00527a074
• 作为产物：
  描述：

  propanethial S-oxide 以 苯 为溶剂， 反应 168.0h， 生成 trans-3,4-diethyl-1,2-dithietane 1,1-dioxide
  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

• BLOCK E.; BAZZI A. A.; REVELLE L. K., J. AMER. CHEM. SOC., 1980, 102, NO 7, 2490-2491
  作者：BLOCK E.、 BAZZI A. A.、 REVELLE L. K.

  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. 6. Dimer of the onion lachrymatory factor: the first stable 1,2-dithietane derivative
  作者：Eric Block、Ali A. Bazzi、Larry K. Revelle

  DOI：10.1021/ja00527a074

  日期：1980.3