3-((E)-4-Ethylsulfanyl-but-3-en-1-ynyl)-thiophene | 143799-31-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 3-((E)-4-Ethylsulfanyl-but-3-en-1-ynyl)-thiophene
• CAS: 143799-31-9
• 化学式: C₁₀H₁₀S₂
• 分子量: 194.321
• InChiKey: DHCLXUWHKCILOB-UHFFFAOYSA-N

物化性质

• 沸点：
  289.8±36.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.37
• 重原子数：
  12.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-((E)-4-Ethylsulfanyl-but-3-en-1-ynyl)-thiophene 在 锌 作用下， 以 乙醇 为溶剂， 以71%的产率得到3-((1Z,3E)-4-Ethylsulfanyl-buta-1,3-dienyl)-thiophene
  参考文献：
  名称：

  A stereoselective synthesis of 1-phenyl-1-buten-3-yne and some 1-heteroaryl analogues.

  摘要：

  Z-Enynes, RCH=CHC=CH (R= phenyl, 2-furyl, 2- and 3-thienyl and 3-pyridyl) can be obtained in approximately 40% overall yields and with a stereoselectivity of > 95% by Pd/Cu-catalyzed cross-coupling of the readily available enyne sulfide HC=CCH=CHSC2H5 with RBr and RI, reduction of the products with activated zinc powder in ethanol and elimination of ethanethiol from the reduction products RCH=CHCH=CHSC2H5 with an excess of sodamide in liquid ammonia. In the case of the 2-pyridyl-substituted substrate the E-enyne HC=CCH=CH-2-pyridyl is isolated.

  DOI：

  10.1016/s0040-4039(00)74696-x
• 作为产物：
  描述：

  3-碘噻吩 、 1-ethylthio-1-buten-3-yne 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(I) bromide 三乙胺 、 三苯基膦 作用下， 反应 1.0h， 以77%的产率得到3-((E)-4-Ethylsulfanyl-but-3-en-1-ynyl)-thiophene
  参考文献：
  名称：

  A stereoselective synthesis of 1-phenyl-1-buten-3-yne and some 1-heteroaryl analogues.

  摘要：

  Z-Enynes, RCH=CHC=CH (R= phenyl, 2-furyl, 2- and 3-thienyl and 3-pyridyl) can be obtained in approximately 40% overall yields and with a stereoselectivity of > 95% by Pd/Cu-catalyzed cross-coupling of the readily available enyne sulfide HC=CCH=CHSC2H5 with RBr and RI, reduction of the products with activated zinc powder in ethanol and elimination of ethanethiol from the reduction products RCH=CHCH=CHSC2H5 with an excess of sodamide in liquid ammonia. In the case of the 2-pyridyl-substituted substrate the E-enyne HC=CCH=CH-2-pyridyl is isolated.

  DOI：

  10.1016/s0040-4039(00)74696-x