methyl 2-(trimethylsilyl)vinyl sulfide | 70127-60-5

• 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: methyl 2-(trimethylsilyl)vinyl sulfide
• 英文别名: trimethyl-[(E)-2-methylsulfanylethenyl]silane
• CAS: 70127-60-5
• 化学式: C₆H₁₄SSi
• 分子量: 146.329
• InChiKey: CKTLEUAHBBMISO-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.74
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-methylthio-2-(trimethylsilyl)ethyne 在 lithium aluminium tetrahydride 作用下， 以 三甘醇二甲醚 为溶剂， 反应 20.0h， 以60%的产率得到methyl 2-(trimethylsilyl)vinyl sulfide
  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

• BOPOHKOB M. G.; RAXLIN V. I.; MIRSKOV R. G.; XANGAZHEEV S. X.; YAROSH O. +, ZH. OBSHCH. XIMII, 1979, 49, HO 1, 119-126
  作者：BOPOHKOB M. G.、 RAXLIN V. I.、 MIRSKOV R. G.、 XANGAZHEEV S. X.、 YAROSH O. +

  DOI：——

  日期：——
• 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.