4-[2,2-bis(ethylthio)vinyl]-2,2-bis(ethylthio)chroman | 349449-74-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 4-[2,2-bis(ethylthio)vinyl]-2,2-bis(ethylthio)chroman
• 英文别名: 4-[2,2-Bis(ethylsulfanyl)ethenyl]-2,2-bis(ethylsulfanyl)-3,4-dihydrochromene
• CAS: 349449-74-7
• 化学式: C₁₉H₂₈OS₄
• 分子量: 400.695
• InChiKey: KGSGVWDLIWKCGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  110
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-[2,2-bis(ethylthio)vinyl]-2,2-bis(ethylthio)chroman 在 水 、 copper(II) oxide 、 copper dichloride 作用下， 以 丙酮 为溶剂， 反应 1.0h， 以80%的产率得到4-[β,β-bis(ethylthio)vinyl]-3,4-dihydrocoumarin
  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
• 作为产物：
  描述：

  水杨醛 、 1,1-bis(ethylthio)-2-trimethylsilylethene 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以58%的产率得到4-[2,2-bis(ethylthio)vinyl]-2,2-bis(ethylthio)chroman
  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

• Acid-Promoted Reaction of Trimethylsilylketene Bis(ethylthio)acetal with Imines. Synthesis of γ,γ-Bis(ethylthio)allylamines
  作者：Shuhei Yahiro、Keisuke Shibata、Takeshi Saito、Tatsuo Okauchi、Toru Minami

  DOI：10.1021/jo020748v

  日期：2003.6.1

  Pestalotiopsis microspora (top right), an endophytic fungus commonly found in tropical plants, was cultured from the lesions in a pandanus leaf (top left). The bioactive ambuic acid (lower right), produced by P. microspora, provides an ideal illustration for the recently developed solid-state NMR FIREMAT technique (see representative spectra lower left), from which the stereochemistry and other structural features may be obtained when single-crystal X-ray results are unavailable. See Grant and co-workers, p 4609.
• 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.