2-(ethylthio)furan | 4218-14-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-(ethylthio)furan
• 英文别名: 2-ethylsulfanyl-furan；2-Aethylmercapto-furan；2-Ethylthiofuran；2-ethylsulfanylfuran
• CAS: 4218-14-8
• 化学式: C₆H₈OS
• 分子量: 128.195
• InChiKey: CGCOPLAFHQVQEL-UHFFFAOYSA-N

物化性质

• 保留指数：
  937;937

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  38.4
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2932190090

反应信息

• 作为反应物：
  描述：

  2-(ethylthio)furan 在 sodium hydroxide 、 正丁基锂 、 四丁基溴化铵 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 13.0h， 生成 2-Ethylsulfonyl-5-(3-prop-2-ynoxypentan-3-yl)furan
  参考文献：
  名称：

  Intramolecular Diels−Alder Reaction of Furans with Allenyl Ethers Followed by Sulfur and Silicon Atom-Containing Group Rearrangement

  摘要：

  The intramolecular Diels-Alder reactions of a furandiene with an allenyl ether dienophile followed by the alkylthio, alkylsulfinyl, alkylsulfonyl, and trimethylsilyl group rearrangements are reported. Refluxing the propargyl ether 3 with t-BuOK in t-BuOH at 85 degrees C gave the 1,4-rearrangement product 4 exclusively. The alkylthio group 1,4-rearrangement may proceed intramolecularly via the tight; ion pairs. Refluxing the 5-(alkylsulfinyl)-2-furfuryl propargyl ethers 9a-e and the 5-(alkylsulfonyl)-2-furfuryl propargyl ethers 19a-e under the same reaction conditions gave the alkylsulfinyl group and the alkylsulfonyl group 1,2-rearrangement products 10a-e and 20a-e, respectively. No detectable amount of the corresponding 1,4-rearrangement products 11a-e and 21a-e was obtained. In the cases of 9b and 19b, which possess two furfurylic hydrogen atoms, no detectable amount of the furan ring-transfer reaction products was obtained. Refluxing the 5-(trimethylsilyl)-2-furfuryl propargyl ethers 25a-d with t-BuOK in t-BuOH at 85 degrees C for 10 h gave the trimethylsilyl group 1,2-rearrangement products 26a-d and Brook rearrangement products 27a-d. The reaction mechanisms for these novel intramolecular Diels-Alder reactions are discussed. In the case of 37, which possesses two furfurylic hydrogen atoms, compound 38 was obtained via an intramolecular Diels-Alder reaction followed by the furan ring-transfer reaction and Brook rearrangement.

  DOI：

  10.1021/jo980240l
• 作为产物：
  描述：

  呋喃 、 二乙基二硫醚 在 正丁基锂 作用下， 生成 2-(ethylthio)furan
  参考文献：
  名称：

  Intramolecular Diels−Alder Reaction of Furans with Allenyl Ethers Followed by Sulfur and Silicon Atom-Containing Group Rearrangement

  摘要：

  The intramolecular Diels-Alder reactions of a furandiene with an allenyl ether dienophile followed by the alkylthio, alkylsulfinyl, alkylsulfonyl, and trimethylsilyl group rearrangements are reported. Refluxing the propargyl ether 3 with t-BuOK in t-BuOH at 85 degrees C gave the 1,4-rearrangement product 4 exclusively. The alkylthio group 1,4-rearrangement may proceed intramolecularly via the tight; ion pairs. Refluxing the 5-(alkylsulfinyl)-2-furfuryl propargyl ethers 9a-e and the 5-(alkylsulfonyl)-2-furfuryl propargyl ethers 19a-e under the same reaction conditions gave the alkylsulfinyl group and the alkylsulfonyl group 1,2-rearrangement products 10a-e and 20a-e, respectively. No detectable amount of the corresponding 1,4-rearrangement products 11a-e and 21a-e was obtained. In the cases of 9b and 19b, which possess two furfurylic hydrogen atoms, no detectable amount of the furan ring-transfer reaction products was obtained. Refluxing the 5-(trimethylsilyl)-2-furfuryl propargyl ethers 25a-d with t-BuOK in t-BuOH at 85 degrees C for 10 h gave the trimethylsilyl group 1,2-rearrangement products 26a-d and Brook rearrangement products 27a-d. The reaction mechanisms for these novel intramolecular Diels-Alder reactions are discussed. In the case of 37, which possesses two furfurylic hydrogen atoms, compound 38 was obtained via an intramolecular Diels-Alder reaction followed by the furan ring-transfer reaction and Brook rearrangement.

  DOI：

  10.1021/jo980240l

文献信息

• Dichloroketene-Induced Cyclizations of Vinyl Sulfilimines:  Application of the Method in the Synthesis of (±)-Desoxyeseroline
  作者：Albert Padwa、Shinji Nara、Qiu Wang

  DOI：10.1021/jo051550o

  日期：2005.10.1

  to yield thioalkyl-substituted γ-lactams. The overall process involves nucleophilic addition of the nitrogen atom of the sulfilimine onto the highly electrophilic dichloroketene to first generate a zwitterionic intermediate. A subsequent [3,3]-sigmatropic rearrangement is followed by intramolecular trapping of the Pummerer cation by the amido anion to furnish the observed γ-lactam product. Incorporation

  几种芳基，呋喃基和乙烯基取代的亚硫亚胺与二氯乙烯酮的反应在25°C下进行，得到硫代烷基取代的γ-内酰胺。整个过程包括将亚硫亚胺的氮原子亲核加成到高度亲电的二氯乙烯酮上，首先产生两性离子中间体。随后的[3,3]-σ重排，随后是酰胺阴离子在分子内捕获Pummerer阳离子，以提供所观察到的γ-内酰胺产物。当使用芳基取代的亚硫亚胺时，在磺酰基官能团的芳环上引入供体基团几乎没有影响，但是对与呋喃基取代的体系的反应效率显示出主要影响。电子给体基团的位置（即，磺酰基芳基上的OMe）提高了包含在sulf离子中间体中的酰胺基阴离子的亲核性，并促进了3，3-σ重排的速率。苯乙烯基取代的亚硫亚胺以立体有择的方式环化，并生成γ-内酰胺和异构的亚氨基-内酯体系的3：2混合物。高度官能化的γ-内酰胺易于转化为多种含氮底物。乙烯基亚砜亚胺环化方法应用于卡拉巴尔生物碱（±）-脱氧七氢呋喃的全合成。高度官能化的γ-内酰胺
• A New Synthesis of γ-Lactams Based on the Reaction of Vinyl Sulfilimines with Dichloroketene
  作者：Qiu Wang、Shinji Nara、Albert Padwa

  DOI：10.1021/ol047453j

  日期：2005.3.1

  The reactions of several aryl-, furanyl-, and vinyl substituted sulfilimines with dichloroketene proceeded at 25 degrees C to yield thioalkyl substituted gamma-lactams which, in turn, were converted to a variety of nitrogen-containing substrates. [reaction: see text]

  几种芳基，呋喃基和乙烯基取代的亚硫亚胺与二氯乙烯的反应在25℃进行，得到硫代烷基取代的γ-内酰胺，然后将其转化为多种含氮底物。[反应：看文字]
• Thioethers from Halogen Compounds and Cuprous Mercaptides. II
  作者：Roger Adams、Aldo Ferretti

  DOI：10.1021/ja01527a042

  日期：1959.9
• Mono- and bi-nuclear complexes of the rigid bidentate ligand 2-ethylthio-5-diphenylphosphinofuran
  作者：Mario Bressan、Antonino Morvillo、John M. Brown

  DOI：10.1016/0022-328x(89)85389-6

  日期：1989.2
• US4130562A
  申请人：——

  公开号：US4130562A

  公开（公告）日：1978-12-19