3-<(2-furylmethyl)dithio>-2-butanone | 159113-17-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 3-<(2-furylmethyl)dithio>-2-butanone
• 英文别名: 2-furfuryl 2-oxo-3-butyl disulfide；3-(furan-2-ylmethyldisulfanyl)butan-2-one
• CAS: 159113-17-4
• 化学式: C₉H₁₂O₂S₂
• 分子量: 216.325
• InChiKey: LOGIPTDAOGQBBJ-UHFFFAOYSA-N

物化性质

• 保留指数：
  1604;1577;1577;1589

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  80.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-巯基-2-丁酮 、 糠基硫醇 在 copper(II) sulfate 作用下， 以 乙醚 为溶剂， 反应 0.58h， 生成 3-<(2-furylmethyl)dithio>-2-butanone
  参考文献：
  名称：

  Evaluation of the Key Odorants in a Thermally Treated Solution of Ribose and Cysteine by Aroma Extract Dilution Techniques

  摘要：

  Application of the aroma extract dilution analysis on a solvent extract isolated from a thermally treated solution (145 degrees C; 20 min) of cysteine/ribose led to the identification of 2-furfurylthiol, 3-mercapto-2-pentanone, 2-methyl-3-furanthiol, 5-acetyl-2,3-dihydro-1,4-thiazine, 3-mercapto-2-butanone, and bis(2-methyl-3-furyl) disulfide showing the highest flavor dilution factors among the 29 odor-active volatiles. HRGC/olfactometry of decreasing headspace volumes established especially 2-furfurylthiol and 2-methyl-3-furanthiol as important odorants and revealed 2-thenyl mercaptan and ethyl mercaptan as further key contributors to the overall roasty, meatlike, sulfury odor of the model mixture. 5-Acetyl-2,3-dihydro-1,4-thiazine, identified for the first time among the volatiles of Maillard model reactions or foods, exhibited an intense roasty, popcorn-like odor at the low odor threshold of 0.06 ng/L of air, which was of the same order of magnitude as those reported in the literature for the roasty-smelling odorants 2-acetyl-1-pyrroline and 2-acetyl-2-thiazoline.

  DOI：

  10.1021/jf00056a042

文献信息

• Practical synthesis of unsymmetrical disulfides promoted by bromodimethylsulfonium bromide
  作者：Bo Dong、Yifeng Chen、Shubing Xie、Jieying Zhang、Jian Shen、Lan-Gui Xie

  DOI：10.1039/d2ob02124b

  日期：——

  Oxidative cross-coupling of two thiols is the most direct tool for the synthesis of unsymmetrical disulfides and highly desirable across academia and industry. However, the inevitable formation of significant amounts of the corresponding symmetrical by-products is a major issue. We herein present a method toward the synthesis of unsymmetrical disulfides in which the homo-coupling of the thiols is effectively

  两个硫醇的氧化交叉偶联是合成不对称二硫化物的最直接工具，在学术界和工业界都非常受欢迎。然而，不可避免地形成大量相应的对称副产物是一个主要问题。我们在此提出了一种合成不对称二硫化物的方法，其中通过顺序添加两种硫醇，利用溴二甲硫溴化硫对硫醇的快速氧化，有效地抑制了硫醇的自偶联。
• Some Novel Meatlike Aroma Compounds from the Reactions of Alkanediones with Hydrogen Sulfide and Furanthiols
  作者：Donald S. Mottram、Marta S. Madruga、Frank B. Whitfield

  DOI：10.1021/jf00049a035

  日期：1995.1

  The products of reactions of hydrogen sulfide with 2,3-butanedione and with 2,3-pentanedione in dilute ethanolic solution were analyzed by CC-MS and CC-odor port analysis. Components were also collected from the GC column and analyzed by H-1 NMR. Mercaptoketones were formed which readily oxidized to the corresponding disulfides with traces of mono- and trisulfides. When 2-methyl-3-furanthiol or 2-furylmethanethiol was added to the reaction mixtures, a series of disulfides containing alkanone, 2-methyl-3-furyl and 2-furanmethyl moieties were formed. Some of these compounds have been found recently in the volatiles of cooked meat and in meatlike model systems. GC-odor port evaluation of the components of the reaction systems showed that disulfides containing the 2-methyl-3-furyl group had meaty aromas, whereas those without this group were sulfurous or onion-like in character.