1,1-bis(ethylthio)-2-trimethylsilylethene | 349449-55-4

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 1,1-bis(ethylthio)-2-trimethylsilylethene
• 英文别名: Silane, [2,2-bis(ethylthio)ethenyl]trimethyl-；2,2-bis(ethylsulfanyl)ethenyl-trimethylsilane
• CAS: 349449-55-4
• 化学式: C₉H₂₀S₂Si
• 分子量: 220.475
• InChiKey: BFTOOISGTZWBBF-UHFFFAOYSA-N

物化性质

• 沸点：
  200.8±25.0 °C(Predicted)
• 密度：
  0.941±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.21
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-苄叉苯胺 、 1,1-bis(ethylthio)-2-trimethylsilylethene 在 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 以83%的产率得到1,1,5,5-tetrakis(ethylthio)-3-phenyl-1,4-pentadiene
  参考文献：
  名称：

  Acid-Promoted Reaction of Trimethylsilylketene Bis(ethylthio)acetal with Imines. Synthesis of γ,γ-Bis(ethylthio)allylamines

  摘要：

  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.

  DOI：

  10.1021/jo020748v
• 作为产物：
  描述：

  硫酸二乙酯 、 (Trimethylsilyl)dithioessigsaeure-ethylester 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以81%的产率得到1,1-bis(ethylthio)-2-trimethylsilylethene
  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

• The First Synthesis of Phosphonoacrolein. Application to Diels−Alder Reaction as Heterodiene
  作者：Sadayuki Arimori、Ryoji Kouno、Tatsuo Okauchi、Toru Minami

  DOI：10.1021/jo020403c

  日期：2002.10.1

  hetero-Diels-Alder reaction with electron-rich alkenes 4a-f or alkynes 9a-c under mild conditions, and phosphono-substituted pyrans 5a-d, 6e,f or pyranopyrans 11a-c were obtained in good to excellent yields. The reaction of 3 with cyclopentadiene and cyclohexadiene led to mixtures of [2 + 4] and [4 + 2] cycloadducts 7a, 8a and 7b, 8b in modest yields. The cycloaddition reaction between 3 and pyranopyran

  通过酸处理衍生自β-乙氧基-α-膦酰基乙烯基阴离子和MOMC1的β-乙氧基-α-（甲氧基甲基）乙烯基膦酸酯2，以定量收率制备膦酰基丙烯醛3的第一合成。膦酰基丙烯醛3容易在温和的条件下与富含电子的烯烃4a-f或炔烃9a-c进行异Diels-Alder反应，并且良好地获得了膦酰基取代的吡喃5a-d，6e，f或吡喃吡喃11a-c。高产。3与环戊二烯和环己二烯的反应以中等收率得到[2 + 4]和[4 + 2]环加合物的混合物。3与吡喃并吡喃13或二溴卡宾与13之间的环加成反应以良好的产率产生[4 + 2]或[2 +1]个环加合物。
• 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.
• 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.