1-O-trimethylsilyloxy-3-hexanthiol | 1251531-33-5

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 1-O-trimethylsilyloxy-3-hexanthiol
• CAS: 1251531-33-5
• 化学式: C₉H₂₂OSSi
• 分子量: 206.425
• InChiKey: ABAGQYVMOCZPRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.33
• 重原子数：
  12.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  9.23
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-O-trimethylsilyloxy-3-hexanthiol 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 为溶剂， 100.0 ℃ 、1.2 kPa 条件下， 反应 3.27h， 生成 3-propyl-1,2-oxathiolane-2-oxide
  参考文献：
  名称：

  Elucidation of the 1,3-Sulfanylalcohol Oxidation Mechanism: An Unusual Identification of the Disulfide of 3-Sulfanylhexanol in Sauternes Botrytized Wines

  摘要：

  A four-step purification method was developed to isolate a citrus odorant detected by gas chromatography-olfactometry (GC-O), which was apparently specific to Sauternes botrytized wines. A fragmentation pattern of the odorant was obtained by multidimensional gas chromatography-mass spectrometry-olfactometry (MDGC-MS-O). The exact mass measurement was used to determine its elemental formula as C6H12OS. On the basis of these data, the unusual structure of 3-propyl-1,2-oxathiolane was synthesized and characterized for the first time. This confirmed its identification. Its occurrence in Sauternes wine extracts was demonstrated to result from the thermal oxidative degradation of 3-sulfanylhexanol disulfide (3,3'-disulfanediyldihexan-1-ol) in the GC injector. This disulfide was synthesized and then firmly identified for the first time in Sauternes wine. Although the presence of 3-sulfanylhexanol oxidation products had previously been reported in natural extracts (but not wine), the full oxidation pathway from 3-sulfanylhexanol to 3-propyl-gamma-sultine via 3,3'-disulfanediyldihexan-1-ol was clearly established for the first time. Because the disulfide has mainly been detected in Sauternes botrytized wines, this finding suggested a singular reactivity of 3-sulfanylhexanol in botrytized wines, thus opening up a wide range of new opportunities in wine chemistry.

  DOI：

  10.1021/jf102022s
• 作为产物：
  描述：

  2-(1-hydroxyhexan-3-ylthio)isoindoline-1,3-dione 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 20.0~200.0 ℃ 、1.2 kPa 条件下， 反应 35.27h， 生成 1-O-trimethylsilyloxy-3-hexanthiol
  参考文献：
  名称：

  Elucidation of the 1,3-Sulfanylalcohol Oxidation Mechanism: An Unusual Identification of the Disulfide of 3-Sulfanylhexanol in Sauternes Botrytized Wines

  摘要：

  A four-step purification method was developed to isolate a citrus odorant detected by gas chromatography-olfactometry (GC-O), which was apparently specific to Sauternes botrytized wines. A fragmentation pattern of the odorant was obtained by multidimensional gas chromatography-mass spectrometry-olfactometry (MDGC-MS-O). The exact mass measurement was used to determine its elemental formula as C6H12OS. On the basis of these data, the unusual structure of 3-propyl-1,2-oxathiolane was synthesized and characterized for the first time. This confirmed its identification. Its occurrence in Sauternes wine extracts was demonstrated to result from the thermal oxidative degradation of 3-sulfanylhexanol disulfide (3,3'-disulfanediyldihexan-1-ol) in the GC injector. This disulfide was synthesized and then firmly identified for the first time in Sauternes wine. Although the presence of 3-sulfanylhexanol oxidation products had previously been reported in natural extracts (but not wine), the full oxidation pathway from 3-sulfanylhexanol to 3-propyl-gamma-sultine via 3,3'-disulfanediyldihexan-1-ol was clearly established for the first time. Because the disulfide has mainly been detected in Sauternes botrytized wines, this finding suggested a singular reactivity of 3-sulfanylhexanol in botrytized wines, thus opening up a wide range of new opportunities in wine chemistry.

  DOI：

  10.1021/jf102022s

文献信息

• Elucidation of the 1,3-Sulfanylalcohol Oxidation Mechanism: An Unusual Identification of the Disulfide of 3-Sulfanylhexanol in Sauternes Botrytized Wines
  作者：Elise Sarrazin、Svitlana Shinkaruk、Monique Pons、Cecile Thibon、Bernard Bennetau、Philippe Darriet

  DOI：10.1021/jf102022s

  日期：2010.10.13

  A four-step purification method was developed to isolate a citrus odorant detected by gas chromatography-olfactometry (GC-O), which was apparently specific to Sauternes botrytized wines. A fragmentation pattern of the odorant was obtained by multidimensional gas chromatography-mass spectrometry-olfactometry (MDGC-MS-O). The exact mass measurement was used to determine its elemental formula as C6H12OS. On the basis of these data, the unusual structure of 3-propyl-1,2-oxathiolane was synthesized and characterized for the first time. This confirmed its identification. Its occurrence in Sauternes wine extracts was demonstrated to result from the thermal oxidative degradation of 3-sulfanylhexanol disulfide (3,3'-disulfanediyldihexan-1-ol) in the GC injector. This disulfide was synthesized and then firmly identified for the first time in Sauternes wine. Although the presence of 3-sulfanylhexanol oxidation products had previously been reported in natural extracts (but not wine), the full oxidation pathway from 3-sulfanylhexanol to 3-propyl-gamma-sultine via 3,3'-disulfanediyldihexan-1-ol was clearly established for the first time. Because the disulfide has mainly been detected in Sauternes botrytized wines, this finding suggested a singular reactivity of 3-sulfanylhexanol in botrytized wines, thus opening up a wide range of new opportunities in wine chemistry.