6-(2-ethynylphenyl)hex-5-yn-1-al | 148290-52-2

• 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: 6-(2-ethynylphenyl)hex-5-yn-1-al
• 英文别名: 6-(2-Ethynylphenyl)-5-hexanal；6-(2-ethynylphenyl)-5-hexynal；6-(2-Ethynylphenyl)hex-5-ynal
• CAS: 148290-52-2
• 化学式: C₁₄H₁₂O
• 分子量: 196.249
• InChiKey: MAFKINVDVHBJKX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-(2-ethynylphenyl)hex-5-yn-1-al 在 manganese(IV) oxide 、 1,4-环己二烯 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 3,4-dihydro-1(2H)-anthracenone
  参考文献：
  名称：

  CDPI3-enediyne and CDPI3-EDTA conjugates: a new class of DNA cleaving agents

  摘要：

  The synthesis and preliminary evaluation of la and lb, prototypical CDPI3-enediyne and CDPI3-EDTA conjugates constituting a new class of DNA cleaving agents, are detailed.

  DOI：

  10.1021/jo00063a019
• 作为产物：
  描述：

  5-己炔-1-醇 在 copper(l) iodide 、 四(三苯基膦)钯 potassium fluoride 、 草酰氯 、 水 、 二甲基亚砜 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 66.25h， 生成 6-(2-ethynylphenyl)hex-5-yn-1-al
  参考文献：
  名称：

  CDPI3-enediyne and CDPI3-EDTA conjugates: a new class of DNA cleaving agents

  摘要：

  The synthesis and preliminary evaluation of la and lb, prototypical CDPI3-enediyne and CDPI3-EDTA conjugates constituting a new class of DNA cleaving agents, are detailed.

  DOI：

  10.1021/jo00063a019

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.
• Synthetic studies of the tandem enediyne-mono- and bisradical cyclizations
  作者：Janet Wisniewski Grissom、Trevor L. Calkins、Miles Egan

  DOI：10.1021/ja00078a013

  日期：1993.12

  The readily synthesized enediynes 12a-j possessing a tethered olefin radical acceptor can participate in a tandem enediyne-radical cyclization to yield dibydrobenzindene derivatives 14a-j. In the present study, the scope of this reaction was expanded to include a wide variety of olefin acceptors. Substitution at both ends of olefin leads to the formation of two diastereomers 14b and 14c in a 3.5:1 ratio when R3 is Me and R2 is CO2Me. The structures of the dihydrobenzindene products 14b and 14c were confirmed by generating a radical from 25 by a tributyltin hydride reaction which undergoes radical cyclization; this radical is similar to the enediyne-generated radical, which also cyclizes. It was shown that, in 14i and 14j, a substituent at R1 slowed the reaction but still resulted in a good to excellent yield of product. A tandem enediyne-6-exo-radical cyclization of 16 was also carried out but did not work as well as its 5-exo counterpart 12a. Finally, an enediyne 33 containing two olefinic tethers was cyclized in a process to form tetracycle 34 where three rings were formed in one synthetic operation.
• Aryl radical additions to aldehydes and oxime ethers: the tandem enediyne-radical cyclization
  作者：Janet Wisniewski Grissom、Detlef Klingberg

  DOI：10.1021/jo00076a011

  日期：1993.11

  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.
• CDPI3-enediyne and CDPI3-EDTA conjugates: a new class of DNA cleaving agents
  作者：Dale L. Boger、Jiacheng Zhou

  DOI：10.1021/jo00063a019

  日期：1993.5

  The synthesis and preliminary evaluation of la and lb, prototypical CDPI3-enediyne and CDPI3-EDTA conjugates constituting a new class of DNA cleaving agents, are detailed.