2,3-bis(ethylthio)-5-methyl-4-phenylfuran

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2,3-bis(ethylthio)-5-methyl-4-phenylfuran
• 英文别名: 2,3-Bis(ethylsulfanyl)-5-methyl-4-phenylfuran
• 化学式: C₁₅H₁₈OS₂
• 分子量: 278.439
• InChiKey: KSCKUNAHFMWZKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-苯基-1,2-丙二酮 、 1,1-bis(ethylthio)-2-trimethylsilylethene 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以27%的产率得到2,3-bis(ethylthio)-5-methyl-4-phenylfuran
  参考文献：
  名称：

  Lewis Acid-Promoted Deoxygenative Di[β,β-bis(ethylthio)]vinylation of Aldehydes with Trimethylsilylketene Bis(ethylthio)acetal

  摘要：

  Silylketene dithioacetal 1 reacted with aldehydes 2a-o, 14, or cinnamaldehyde (11) in the presence of Lewis acid to give deoxygenative divinylation products, 3-substituted 1,4-pentadienes 3a-o, 15, or 5-phenyl-1,3,6-heptatriene 13b, in good to moderate yields. Similar reaction with 2-aminobenzaldehyde (16) or salicylaldehyde (17) produced quinoline 19 or chroman 20 in 40-58% yield. Treatment of 1 with a-diketones 22a-c or a-ketoester 24 led to tetrasubstituted furans 23a-c or allylic alcohol 25, respectively, in rather low yields. The formation mechanisms of these products are discussed.

  DOI：

  10.1021/jo010007e

文献信息

• Lewis Acid-Promoted Deoxygenative Di[β,β-bis(ethylthio)]vinylation of Aldehydes with Trimethylsilylketene Bis(ethylthio)acetal
  作者：Tatsuo Okauchi、Tatsuyoshi Tanaka、Toru Minami

  DOI：10.1021/jo010007e

  日期：2001.6.1

  Silylketene dithioacetal 1 reacted with aldehydes 2a-o, 14, or cinnamaldehyde (11) in the presence of Lewis acid to give deoxygenative divinylation products, 3-substituted 1,4-pentadienes 3a-o, 15, or 5-phenyl-1,3,6-heptatriene 13b, in good to moderate yields. Similar reaction with 2-aminobenzaldehyde (16) or salicylaldehyde (17) produced quinoline 19 or chroman 20 in 40-58% yield. Treatment of 1 with a-diketones 22a-c or a-ketoester 24 led to tetrasubstituted furans 23a-c or allylic alcohol 25, respectively, in rather low yields. The formation mechanisms of these products are discussed.