1-(2-((2,6-dimethylphenyl)ethynyl)phenyl)-3-(trimethylsilyl)prop-2-ynyl acetate | 1422529-05-2

• 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: 1-(2-((2,6-dimethylphenyl)ethynyl)phenyl)-3-(trimethylsilyl)prop-2-ynyl acetate
• 英文别名: [1-[2-[2-(2,6-Dimethylphenyl)ethynyl]phenyl]-3-trimethylsilylprop-2-ynyl] acetate
• CAS: 1422529-05-2
• 化学式: C₂₄H₂₆O₂Si
• 分子量: 374.555
• InChiKey: WMYPKOMHABAIAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.19
• 重原子数：
  27.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-(2-((2,6-dimethylphenyl)ethynyl)phenyl)-3-(trimethylsilyl)prop-2-ynyl acetate 、 M-TOLYLMAGNESIUM BROMIDE 在 zinc(II) chloride 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 14.25h， 以80%的产率得到[3-[2-(2,6-dimethylphenylethynyl)phenyl]-1-m-tolylpropa-1,2-dienyl]trimethylsilane
  参考文献：
  名称：

  Nonstatistical Dynamic Effects in the Thermal C²–C⁶ Diels–Alder Cyclization of Enyne–Allenes

  摘要：

  The Diels-Alder (DA) reaction channel of the thermal C-2-C-6 (Schmittel) cyclization of enyne-allenes is studied computationally and experimentally evaluating the influence of temperature on product ratios. Remote substituents at the alkyne terminus influence the mechanism of the C-2-C-6/DA cyclization steering it either to a stepwise or a concerted course. Temperature independent product ratios, selectivity of product formation, and computational results obtained at (U)BLYP/6-31G(d) level unveil a mechanism that is strongly controlled by nonstatistical dynamics.

  DOI：

  10.1021/jo302524a
• 作为产物：
  描述：

  2-((2,6-dimethylphenyl)ethynyl)benzaldehyde 在 4-二甲氨基吡啶 、 乙基溴化镁 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 1-(2-((2,6-dimethylphenyl)ethynyl)phenyl)-3-(trimethylsilyl)prop-2-ynyl acetate
  参考文献：
  名称：

  Nonstatistical Dynamic Effects in the Thermal C²–C⁶ Diels–Alder Cyclization of Enyne–Allenes

  摘要：

  The Diels-Alder (DA) reaction channel of the thermal C-2-C-6 (Schmittel) cyclization of enyne-allenes is studied computationally and experimentally evaluating the influence of temperature on product ratios. Remote substituents at the alkyne terminus influence the mechanism of the C-2-C-6/DA cyclization steering it either to a stepwise or a concerted course. Temperature independent product ratios, selectivity of product formation, and computational results obtained at (U)BLYP/6-31G(d) level unveil a mechanism that is strongly controlled by nonstatistical dynamics.

  DOI：

  10.1021/jo302524a