2-methylene-4-phenyl-3-butyn-1-yl tosylate | 66303-62-6

• 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: 2-methylene-4-phenyl-3-butyn-1-yl tosylate
• CAS: 66303-62-6
• 化学式: C₁₈H₁₆O₃S
• 分子量: 312.389
• InChiKey: KYUMKBYTMJOLKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.31
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  六羰基钨 、 2-methylene-4-phenyl-3-butyn-1-yl tosylate 、 sodium cyclopentadienide 以 四氢呋喃 为溶剂， 以68%的产率得到CpW(CO)3(η(1)-2-methylene-4-phenyl-3-butyn-1-yl)
  参考文献：
  名称：

  Synthesis, Protonation, and Electrophilic Alkylation of CpW(CO)₂[η³-2-(phenylethynyl)allyl]

  摘要：

  CpW(CO)(2)[eta(3)-2-(phenylethynyl)ally] (2) was prepared from the reaction between CpW(CO)(3)Na and 2-methylene-4-phenyl-3-butyn-1-yl tosylate, followed by decarbonylation with Me(3)NO. Treatment of 2 with CF3SO3H in cold CDCl3 produced a mixture of [CpW(CO)(2)(eta(4)-1-(benzylidene)trimethylenemethane)]X (3a) and CpW(CO)(2)(eta(3)-2-CH(2)X-4-phenyl-2,3-butadien-1-yl) (3b) (X = CF3SO3), which were characterized with H-1 and C-13 NMR spectra, Treatment of this mixture (3a,b) with a variety of nucleophiles gave compounds of the type CpW(CO)(2)(eta(3)-2-CH(2)X-4-phenyl-2,3-butadien-1-yl) (X = OH (4a), OMe (4b), iBuNH (4c), Me (4d), Ph (4e), CCPh (4f), H (4g)). In the presence of Bu(4)NI, protonation of 4d-e with CF3SO3H in cold CH2Cl2 produced CPW(CO)I[eta 4-(2-PhCH(2)-3-XCHs)vinylketene] (X = Me (6a), Ph (6b)), the structural identity of which was established from an X-ray diffraction study of the analogous complex CpW(CO)I[eta(4)-(2-PhCH(2)-3-ICH2)vinylketene] (6c). Treatment of 2 with a mixture of acetaldehyde and BF3 . Et(2)O in cold CH2Cl2, followed by reduction of NaBH3CN gave CpW(CO)(2)(eta(3)-2-methyl-4-phenyl-5-methyl-2, 4-pentadien-1-yl) (7), which was characterized by X-ray structural analysis.

  DOI：

  10.1021/om9507989
• 作为产物：
  描述：

  2-(2-Methylene-4-phenyl-but-3-ynyloxy)-tetrahydro-pyran 在 硫酸 作用下， 生成 2-methylene-4-phenyl-3-butyn-1-yl tosylate
  参考文献：
  名称：

  Preparation and solvolysis of 2-alkynyl-, 2-cyclopropyl-, and 2-arylallyl alcohol tosylates. 3. Relationship among allyl and cyclopropyl cations

  摘要：

  DOI：

  10.1021/jo00408a014