5-(2-ethynylphenyl)pent-4-yn-1-ol` | 151860-01-4

• 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: 5-(2-ethynylphenyl)pent-4-yn-1-ol`
• 英文别名: 5-(2-Ethynylphenyl)-4-pentyn-1-ol；5-(2-Ethynylphenyl)pent-4-yn-1-ol
• CAS: 151860-01-4
• 化学式: C₁₃H₁₂O
• 分子量: 184.238
• InChiKey: KMHJMOYPITVMPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.79
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  5-(2-ethynylphenyl)pent-4-yn-1-ol` 在 3,5-二氯吡啶 N-氧化物 、 [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]gold bis(trifluoromethanesulfonyl)imidate 作用下， 以 1,2-二氯乙烷 、 叔丁醇 为溶剂， 反应 5.0h， 以24 mg的产率得到3,4,5,6-tetrahydro-1H-indeno[1,2-c]oxepin-1-one
  参考文献：
  名称：

  双重金催化的三组分反应：通过亚乙烯基金中间体高效合成茚满的酯，酸和内酯

  摘要：

  开发了一种双金（I）催化的三组分反应，以分子间和分子内方式由二炔，醇和吡啶N-氧化物制备茚稠合的羧酸衍生物。吡啶N-氧化物具有独特的反应性和选择性，可以氧化亚乙烯基金。实验研究和DFT计算支持乙烯酮的形成为关键步骤。

  DOI：

  10.1002/ejoc.201700084
• 作为产物：
  描述：

  5-<2-<(Trimetylsilyl)ethynyl>phenyl>pent-4-yn-1-ol 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以97%的产率得到5-(2-ethynylphenyl)pent-4-yn-1-ol`
  参考文献：
  名称：

  Aryl radical additions to aldehydes and oxime ethers: the tandem enediyne-radical cyclization

  摘要：

  The previously unreported cyclization of aryl radicals onto aldehyde and oxime ether acceptors is described. The aryl radicals were generated from a cyclization of enediyne substrates. The aldehydes 6 and 9 and the oxime ethers 7 and 10 were heated to 190-degrees-C in chlorobenzene in the presence of 1,4-cyclohexadiene as a hydrogen atom source to yield the tandem enediyne-radical cyclization products 11a, 11b, 14, 21, and 22, and the simple enediyne cyclization products 12, 13, 15, 16, and 23. For the enediyne aldehyde substrates tandem enediyne-radical cyclization does not appear to be a synthetically useful process and a mixture of products was obtained. The aryl radicals generated in these enediyne cyclizations subsequently undergo either a radical cyclization or other reactions such as hydrogen abstraction from 1,4-cyclohexadiene, decarbonylation, or intramolecular 1,5- and 1,6-hydrogen abstractions. In contrast, there actions with oxime ether precursors provide the tandem enediyne-radical cyclization products in good yield and provide a useful alternative to the tandem enediyne-6-exo-radical cyclization onto olefins.

  DOI：

  10.1021/jo00076a011

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.