4-(1-butynyl)acetophenone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(1-butynyl)acetophenone
• 英文别名: 1-(4-But-1-ynylphenyl)ethanone
• 化学式: C₁₂H₁₂O
• 分子量: 172.227
• InChiKey: UQYREEMBZYZRAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  4-(1-butynyl)acetophenone 、 乙二醇 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 17.0h， 生成 2-(4-but-1-ynylphenyl)-2-methyl-[1,3]dioxolane
  参考文献：
  名称：

  Catalytic Nitrile-Alkyne Cross-Metathesis

  摘要：

  The first catalytic cross-metathesis reaction of an alkyne with a nitrile is described. The nitride complex NW(OC(CF3)(2)CH3)(3)(DME) undergoes reversible triple-bond metathesis reactions with alkynes (RCCR; R = Et, 4-C6H4OMe), forming the alkylidyne complexes RCW(OC(CF3)(2)CH3)(3)(DME) (R = Et, 4-C6H4OMe) along with the corresponding nitrile RCN. This has been exploited to effect catalytic cross-metathesis of nitriles with alkynes, in which the organic CR fragments of two nitriles are coupled to yield an alkyne. A simple "sacrificial" alkyne (3-hexyne) acts as the N-atom acceptor, forming two equivalents of nitrile byproduct (propionitrile).

  DOI：

  10.1021/ja0693439
• 作为产物：
  描述：

  1-丁炔 、 4-溴苯乙酮 在 tris(dibenzylideneacetone)dipalladium (0) copper(l) iodide 、 三乙胺 、 三苯基膦 作用下， 反应 22.5h， 以60%的产率得到4-(1-butynyl)acetophenone
  参考文献：
  名称：

  Catalytic Nitrile-Alkyne Cross-Metathesis

  摘要：

  The first catalytic cross-metathesis reaction of an alkyne with a nitrile is described. The nitride complex NW(OC(CF3)(2)CH3)(3)(DME) undergoes reversible triple-bond metathesis reactions with alkynes (RCCR; R = Et, 4-C6H4OMe), forming the alkylidyne complexes RCW(OC(CF3)(2)CH3)(3)(DME) (R = Et, 4-C6H4OMe) along with the corresponding nitrile RCN. This has been exploited to effect catalytic cross-metathesis of nitriles with alkynes, in which the organic CR fragments of two nitriles are coupled to yield an alkyne. A simple "sacrificial" alkyne (3-hexyne) acts as the N-atom acceptor, forming two equivalents of nitrile byproduct (propionitrile).

  DOI：

  10.1021/ja0693439

文献信息

• BISUBSTRATE INHIBITORS OF PROTEIN KINASES AS THERAPEUTIC AGENTS
  申请人：Parang Keykavous

  公开号：US20110034670A1

  公开（公告）日：2011-02-10

  A bisubstrate inhibitor of Src kinases, having a nucleotide or N-heteroaromatic moiety; and a peptide/phosphopeptide, peptidomimetic, or phosphopeptide mimic moiety. The moieties are linked by a rigid or a flexible linker. The nucleotide or N-heteroaromatic moiety is ATP, ATP-mimics, N-heteroaromatics including purine-based derivatives, pyrimidine-based derivatives such as 2,4-diamino-5-substituted pyrimidine derivatives, pyrazole[3,4-d]pyrimidine derivatives, pyrrolo[2,3-d]pyrimidine derivatives, pyrido[2,3-d]pyrimidine derivatives, amino-substituted dihydropyrimido[4,5-d]pyrimidinone derivatives, thieno- and furo-substituted derivatives, quinazoline derivatives, and quinoline derivatives, and several natural products such as aminogenistein. The phosphopeptide mimics comprise phosphonate-based phosphotyrosine mimetics such as phosphonomethylphenylalanine (Pmp) and its analogues, carboxylic acid-based phosphotyrosine mimetics such as malonyltyrosine or phenylalanine analogues and their derivatives such as carboxymethyl phenylalanine, uncharged pTyr mimetics, and conformationally constrained peptides. The phosphopeptide or phosphopeptide mimics inhibits the Src kinases SH2 domain.
• Catalytic Nitrile-Alkyne Cross-Metathesis
  作者：Andrea M. Geyer、Robyn L. Gdula、Eric S. Wiedner、Marc J. A. Johnson

  DOI：10.1021/ja0693439

  日期：2007.4.1

  The first catalytic cross-metathesis reaction of an alkyne with a nitrile is described. The nitride complex NW(OC(CF3)(2)CH3)(3)(DME) undergoes reversible triple-bond metathesis reactions with alkynes (RCCR; R = Et, 4-C6H4OMe), forming the alkylidyne complexes RCW(OC(CF3)(2)CH3)(3)(DME) (R = Et, 4-C6H4OMe) along with the corresponding nitrile RCN. This has been exploited to effect catalytic cross-metathesis of nitriles with alkynes, in which the organic CR fragments of two nitriles are coupled to yield an alkyne. A simple "sacrificial" alkyne (3-hexyne) acts as the N-atom acceptor, forming two equivalents of nitrile byproduct (propionitrile).