2-[bis(methylthio)methyl]furan | 33500-20-8

• 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: 2-[bis(methylthio)methyl]furan
• 英文别名: 2-dimethylthiomethylfuran；Furfural-dimethyldithioacetal；2-Bis(methylthio)methylfuran；2-[bis(methylsulfanyl)methyl]furan
• CAS: 33500-20-8
• 化学式: C₇H₁₀OS₂
• 分子量: 174.288
• InChiKey: MCRPOGXLCLGHDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[bis(methylthio)methyl]furan 在 盐酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 生成 (4R)-4-<2-(2-furanyl)-2,2-dimethylthio>ethyl-azetidin-2-one
  参考文献：
  名称：

  硫霉素类似物的全合成-III：硫霉素的2-芳基和2-杂芳基类似物的合成

  摘要：

  描述了使用维蒂希环化法形成双环体系的具有和不具有6-羟乙基侧链的2-芳基和2-杂芳基碳青霉烯-2-em-3-羧酸的总合成。讨论了所合成化合物的抗菌活性。

  DOI：

  10.1016/s0040-4020(01)92147-7
• 作为产物：
  描述：

  (E)-5-(Methylthio)pent-2-en-4-inal 在 盐酸 作用下， 以 四氢呋喃 、 氘代氯仿 为溶剂， 反应 72.0h， 以61%的产率得到2-[bis(methylthio)methyl]furan
  参考文献：
  名称：

  摘要：

  Contrary to expectations (Scheme 1), 5-(phenylthio)-(1a) as well as 5-(methylthio)pent-2-en-4-inal (1b) react with a slight excess of HCl to give 2-[bis( phenylthio)methyl] furan (17a, 77% yield) and 2-[bis(methylthio)methyl]furan (17b, 61% yield), respectively. Structures 17a and 17b are supported by the results of an X-ray crystal-structure analysis, by spectroscopic data in comparison to those of model compounds, and by synthesis of 17a. This surprising reaction is tentatively explained by a mechanism (Scheme 4), including a special pyran --> furan ring-contraction sequence, which is in agreement with a labelling experiment.

  DOI：

  10.1002/1522-2675(20000607)83:6<1191::aid-hlca1191>3.0.co;2-x

文献信息

• Yamanishi; Obata, Nippon Nogeikagaku Kaishi, 1953, vol. 27, p. 652
  作者：Yamanishi、Obata

  DOI：——

  日期：——
• Total synthesis of thienamycin analogs—III
  作者：L.D. Cama、Kenneth J. Wildonger、Ravindranath Guthikonda、R.W. Ratcliffe、B.G. Christensen

  DOI：10.1016/s0040-4020(01)92147-7

  日期：1983.1

  The total syntheses of 2-aryl and 2-heteroaryl carbapen-2-em-3-carboxylic acids with and without a 6-hydroxyethyl side chain, using a Wittig cyclization for formation of the bicyclic ring system is described. Antibacterial activity of the compounds synthesized is discussed.

  描述了使用维蒂希环化法形成双环体系的具有和不具有6-羟乙基侧链的2-芳基和2-杂芳基碳青霉烯-2-em-3-羧酸的总合成。讨论了所合成化合物的抗菌活性。
• ——
  作者：Christian Bacilieri、Markus Neuenschwander

  DOI：10.1002/1522-2675(20000607)83:6<1191::aid-hlca1191>3.0.co;2-x

  日期：2000.6.7

  Contrary to expectations (Scheme 1), 5-(phenylthio)-(1a) as well as 5-(methylthio)pent-2-en-4-inal (1b) react with a slight excess of HCl to give 2-[bis( phenylthio)methyl] furan (17a, 77% yield) and 2-[bis(methylthio)methyl]furan (17b, 61% yield), respectively. Structures 17a and 17b are supported by the results of an X-ray crystal-structure analysis, by spectroscopic data in comparison to those of model compounds, and by synthesis of 17a. This surprising reaction is tentatively explained by a mechanism (Scheme 4), including a special pyran --> furan ring-contraction sequence, which is in agreement with a labelling experiment.