(Z)-1-(3-噻吩基)-1-丁烯-3-炔 | 143799-41-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 中文名称: (Z)-1-(3-噻吩基)-1-丁烯-3-炔
• 英文名称: (Z)-1-(3-thienyl)-1-buten-3-yne
• 英文别名: 3-[(Z)-but-1-en-3-ynyl]thiophene
• CAS: 143799-41-1
• 化学式: C₈H₆S
• 分子量: 134.202
• InChiKey: QUJRFSMHBSOJHI-ARJAWSKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (Z)-1-(3-噻吩基)-1-丁烯-3-炔 在 palladium diacetate 、 四(三苯基膦)钯 copper(l) iodide 、 四丁基溴化铵 、 potassium carbonate 、 二乙胺 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 0.08h， 生成 (Z)-bi(6H-cyclopenta[b]thien-6-ylidene)
  参考文献：
  名称：

  Novel Synthesis of Bridged Phenylthienylethenes and Dithienylethenes via Pd-Catalyzed Double-Cyclization Reactions of Diarylhexadienynes

  摘要：

  [reaction: see text] Bridged phenylthienylethenes and dithienylethenes were synthesized via Pd-catalyzed double-cyclization reactions of (Z,Z)-1,6-diaryl-1,5-hexadien-3-ynes. Pd-catalyzed as well as photoinduced Z/E isomerization of the products were also investigated.

  DOI：

  10.1021/ol0600281
• 作为产物：
  描述：

  3-((E)-4-Ethylsulfanyl-but-3-en-1-ynyl)-thiophene 在 氨 、 水 、 sodium amide 、 锌 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 (Z)-1-(3-噻吩基)-1-丁烯-3-炔
  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

文献信息

• A stereoselective synthesis of 1-phenyl-1-buten-3-yne and some 1-heteroaryl analogues.
  作者：Marco Fossatelli、Anca C.T.H.M. van der Kerk、Sergei F. Vasilevsky、Lambert Brandsma

  DOI：10.1016/s0040-4039(00)74696-x

  日期：1992.7

  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.
• Novel Synthesis of Bridged Phenylthienylethenes and Dithienylethenes via Pd-Catalyzed Double-Cyclization Reactions of Diarylhexadienynes
  作者：S. M. Abdur Rahman、Motohiro Sonoda、Miyako Ono、Koji Miki、Yoshito Tobe

  DOI：10.1021/ol0600281

  日期：2006.3.1

  [reaction: see text] Bridged phenylthienylethenes and dithienylethenes were synthesized via Pd-catalyzed double-cyclization reactions of (Z,Z)-1,6-diaryl-1,5-hexadien-3-ynes. Pd-catalyzed as well as photoinduced Z/E isomerization of the products were also investigated.