4-(2-Ethynylphenyl)-3-butyn-1-ol | 159305-98-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(2-Ethynylphenyl)-3-butyn-1-ol
• 英文别名: 4-(2-ethynylphenyl)but-3-yn-1-ol
• CAS: 159305-98-3
• 化学式: C₁₂H₁₀O
• 分子量: 170.211
• InChiKey: ROMSGAGTWYLGCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-(2-Ethynylphenyl)-3-butyn-1-ol 在 PtCl₂/CO 作用下， 以 various solvent(s) 为溶剂， 反应 4.0h， 以83%的产率得到2,3-dihydronaphtho<1,2-b>furan
  参考文献：
  名称：

  Platinum- and Ruthenium-Catalyzed Aromatization of Enediynes via Intramolecular­ Nucleophilic Additions

  摘要：

  利用 TpRuPPh3(MeCN)2PF6 和二氯化铂通过分子内亲核加成实现了烯炔类化合物的催化环化，以良好的产率得到了萘融合的 2,3- 二氢呋喃和吡咯。在实验结果的基础上，提出了亲核加成Ï-炔中间体，然后插入炔的机理。

  DOI：

  10.1055/s-2007-983739
• 作为产物：
  描述：

  1,2-二碘苯 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.25h， 生成 4-(2-Ethynylphenyl)-3-butyn-1-ol
  参考文献：
  名称：

  Enediyne- and Tributyltin Hydride-Mediated Aryl Radical Additions onto Various Radical Acceptors

  摘要：

  Tandem enediyne-radical cyclizations were carried out on substrates that contain nitrile and ketone radical accepters. The products of these cyclizations and the previously reported tandem enediyne-radical cyclizations containing aldehyde and oxime ether radical accepters were compared with tributyltin hydride-mediated aryl radical addition reactions with 1-bromonaphthalene derivatives containing aldehyde, oxime ether, nitrile, and ketone radical accepters, since these substrates go through similar initial radical intermediates. Although many of the same products were observed using either method of aryl radical generation, there were distinct differences in the product composition and identity depending on which method was used. These differences can probably be primarily attributed to the temperature difference of the two modes of radical generation.

  DOI：

  10.1021/jo00104a053

文献信息

• Enediyne- and Tributyltin Hydride-Mediated Aryl Radical Additions onto Various Radical Acceptors
  作者：Janet Wisniewski Grissom、Detlef Klingberg、Sabine Meyenburg、Brenda L. Stallman

  DOI：10.1021/jo00104a053

  日期：1994.12

  Tandem enediyne-radical cyclizations were carried out on substrates that contain nitrile and ketone radical accepters. The products of these cyclizations and the previously reported tandem enediyne-radical cyclizations containing aldehyde and oxime ether radical accepters were compared with tributyltin hydride-mediated aryl radical addition reactions with 1-bromonaphthalene derivatives containing aldehyde, oxime ether, nitrile, and ketone radical accepters, since these substrates go through similar initial radical intermediates. Although many of the same products were observed using either method of aryl radical generation, there were distinct differences in the product composition and identity depending on which method was used. These differences can probably be primarily attributed to the temperature difference of the two modes of radical generation.
• Platinum- and Ruthenium-Catalyzed Aromatization of Enediynes via Intramolecular­ Nucleophilic Additions
  作者：Rai-Shung Liu、Bhanu Taduri、Arjan Odedra、Cheng-Yi Lung

  DOI：10.1055/s-2007-983739

  日期：2007.7

  Catalytic cyclization of enediynes via intramolecular nucleophilic addition was achieved with TpRuPPh3(MeCN)2PF6 and platinum dichloride, giving naphthalene-fused 2,3-dihydrofurans and -pyrroles in good yields. On the basis of experimental results, the mechanism is proposed to involve nucleophilic addition to a π-alkyne intermediate, followed by alkyne insertion.

  利用 TpRuPPh3(MeCN)2PF6 和二氯化铂通过分子内亲核加成实现了烯炔类化合物的催化环化，以良好的产率得到了萘融合的 2,3- 二氢呋喃和吡咯。在实验结果的基础上，提出了亲核加成Ï-炔中间体，然后插入炔的机理。