(E)-5-phenyl-1-(thiophen-2-yl)pent-2-en-4-yn-1-one | 1257555-47-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-5-phenyl-1-(thiophen-2-yl)pent-2-en-4-yn-1-one
• 英文别名: (E)-5-phenyl-1-(thien-2-yl)pent-2-en-4-yn-1-one；(E)-5-phenyl-1-thiophen-2-ylpent-2-en-4-yn-1-one
• CAS: 1257555-47-7
• 化学式: C₁₅H₁₀OS
• 分子量: 238.31
• InChiKey: RLZXLLUUAWYJMT-BJMVGYQFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-5-phenyl-1-(thiophen-2-yl)pent-2-en-4-yn-1-one 在 叠氮化钾 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (E)-3-(5-phenyl-1H-1,2,3-triazol-4-yl)-1-(thiophen-2-yl)prop-2-en-1-one
  参考文献：
  名称：

  Azolyl-substituted 1,2,3-triazoles

  摘要：

  Huisgen reaction of (E)-1,5-diarylpent-2-en-4-yn-1-ones and (E)-1,5-diarylpent-1-en-4-yn-3-ones afforded 1-aryl-3-(5-aryl-1H-1,2,3-triazol-4-yl)prop-2-en-1-ones and 3-aryl-1-(5-aryl-1H-1,2,3-triazol-4-yl)-prop-2-en-1-ones, respectively. (E)-1-Aryl-3-(5-phenyl-1H-1,2,3-triazol-4-yl)prop-2-en-1-ones reacted with hydrazine hydrate and phenylhydrazine to give 72-93% of 4-(3-aryl-4,5-dihydro-1H-pyrazol-5-yl)-5-phenyl-1H-1,2,3-triazoles which underwent dehydrogenation on heating in boiling acetic acid with formation of the corresponding pyrazole derivatives. The molecular structures of (E)-3-phenyl-1-(5-phenyl-1H-1,2,3-triazol-4-yl)prop-2-en-1-one and 4-[3-(4-methylphenyl)-1-phenyl-4,5-dihydro-1H-pyrazol-5-yl]-5-phenyl-1H-1,2,3-triazole were studied by X-ray analysis. 4-(3-Aryl-4,5-dihydro-1H-pyrazol-5-yl)-5-phenyl-1H-1,2,3-triazoles showed toxicity against Daphnia magna.

  DOI：

  10.1134/s1070428016030209
• 作为产物：
  描述：

  2-噻吩甲醛 在 哌啶 、 copper(l) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 (E)-5-phenyl-1-(thiophen-2-yl)pent-2-en-4-yn-1-one
  参考文献：
  名称：

  Stereoselective, Cascade Synthesis of trans-Enynones through Coupling-Isomerization Reaction

  摘要：

  A mild, cascade methodology based on the modified Cadiot-Chodkiewicz reaction was developed for the stereoselective synthesis of trans-enynones. By this methodology, structurally divergent trans-enynones, which are embedded with sensitive functional groups, were synthesized. Control experiments suggested that the CuCl alone does not have a role in the isomerization step, whereas the CuCl piperidine complex (formed during the cross coupling) may have a rate enhancing effect. Furthermore, additional sets of control experiments favor the involvement of unimolecular [1,2]-H shift rather than a homobimolecular proton abstraction during the isomerization step.

  DOI：

  10.1021/acs.joc.5b01780

文献信息

• Stereoselective synthesis of enynones via base-catalyzed isomerization of 1,5-disubstituted-2,4-pentadiynyl silyl ethers or their alcohol derivatives
  作者：Jingjin Chen、Guoqin Fan、Yuanhong Liu

  DOI：10.1039/c0ob00344a

  日期：——

  1,5-Disubstituted-2,4-pentadiynyl silyl ethers undergo smooth desilylative isomerization to afford cis-enynones as major products with moderate stereoselectivities in the presence of a catalytic amount of KOtBu or DBU. While the isomerization reactions of their alcohol derivatives catalyzed by KOH, KOtBu or NaH take place efficiently to produce trans-enynones with high stereoselectivities. These reactions

  1,5-二取代的2,4-戊二炔基甲硅烷基醚经过顺式脱甲硅烷基化异构化反应，以顺式-乙炔酮为主要产物，并在催化量的二甲基甲酰胺存在下，具有中等的立体选择性。KO Ť卜 或者 DBU。而其醇衍生物的异构化反应是通过酸值， KO Ť卜 或者 碳酸氢钠有效地产生具有高立体选择性的反式-乙炔酮。这些反应为合成具有广泛取代基的烯酮提供了方便实用的途径。