trans-3,4-bis(trimethylsilyl)-1,2-dithiethane 1,1-dioxide | 114693-69-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: trans-3,4-bis(trimethylsilyl)-1,2-dithiethane 1,1-dioxide
• 英文别名: trans-3,4-bis(trimethylsilyl)-1,2-dithietane 1,1-dioxide；[(3R,4R)-1,1-dioxo-4-trimethylsilyldithietan-3-yl]-trimethylsilane
• CAS: 114693-69-5
• 化学式: C₈H₂₀O₂S₂Si₂
• 分子量: 268.549
• InChiKey: HVEDNAFCKKFWDS-YUMQZZPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.56
• 重原子数：
  14
• 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-bis(trimethylsilyl)-1,2-dithiethane 1,1-dioxide 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以99%的产率得到dl-1,2-bis(trimethylsilyl)-1,2-ethanedithiol
  参考文献：
  名称：

  Gas-phase determination of the geometric requirements of the silicon .beta.-effect. Photoelectron and Penning ionization electron spectroscopic study of silylthiiranes and -oxiranes. Synthesis and chemistry of trans-2,3-bis(trimethylsilyl)thiirane

  摘要：

  DOI：

  10.1021/ja00222a037
• 作为产物：
  描述：

  (Z)-(trimethylsilyl)methanethial S-oxide 以 氘代氯仿 为溶剂， 反应 48.0h， 以42%的产率得到trans-3,4-bis(trimethylsilyl)-1,2-dithiethane 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