(1-(3-methoxyphenyl)-3-(2-(phenylethynyl)phenyl)propa-1,2-dienyl)trimethylsilane | 1575770-49-8

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: (1-(3-methoxyphenyl)-3-(2-(phenylethynyl)phenyl)propa-1,2-dienyl)trimethylsilane
• CAS: 1575770-49-8
• 化学式: C₂₇H₂₆OSi
• 分子量: 394.588
• InChiKey: KKWRQOBUJPYDHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.67
• 重原子数：
  29.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (1-(3-methoxyphenyl)-3-(2-(phenylethynyl)phenyl)propa-1,2-dienyl)trimethylsilane 以 甲苯 为溶剂， 反应 0.25h， 以53%的产率得到(6-methoxy-5-phenyl-11H-benzo[b]fluoren-10-yl)trimethylsilane
  参考文献：
  名称：

  Quantification of Nonstatistical Dynamics in an Intramolecular Diels–Alder Cyclization without Trajectory Computation

  摘要：

  Experimental and computational (DFT) investigations reveal that enyne-allenes with an aryl group as probe at the allene terminus follow a dynamic non-IRC Diels-Alder cyclization pathway. Starting from two separate C-2-C-6 (Schmittel) transition states (TS), two distinct reaction paths originate that share a common diradical intermediate, however, without mixing! Because the momentum of the initial TS is transmitted into product formation, we suggest a simple protocol without trajectory computations to estimate the fraction of molecules that follow nonstatistical dynamics: It was calculated from the partitioning at the TSs, as derived from DFT computations, and the experimental ratio. The thus-determined percentage of dynamically reacting molecules only slightly depends on the depth of the intermediate well but rather on Delta Delta G double dagger of the initial and the follow-up transition states.

  DOI：

  10.1021/jo500035b
• 作为产物：
  描述：

  1-[2-(phenylethynyl)phenyl]-3-(trimethylsilyl)prop-2-yn-1-yl acetate 、 (3-methoxyphenyl)magnesium 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 0.75h， 以92%的产率得到(1-(3-methoxyphenyl)-3-(2-(phenylethynyl)phenyl)propa-1,2-dienyl)trimethylsilane
  参考文献：
  名称：

  Quantification of Nonstatistical Dynamics in an Intramolecular Diels–Alder Cyclization without Trajectory Computation

  摘要：

  Experimental and computational (DFT) investigations reveal that enyne-allenes with an aryl group as probe at the allene terminus follow a dynamic non-IRC Diels-Alder cyclization pathway. Starting from two separate C-2-C-6 (Schmittel) transition states (TS), two distinct reaction paths originate that share a common diradical intermediate, however, without mixing! Because the momentum of the initial TS is transmitted into product formation, we suggest a simple protocol without trajectory computations to estimate the fraction of molecules that follow nonstatistical dynamics: It was calculated from the partitioning at the TSs, as derived from DFT computations, and the experimental ratio. The thus-determined percentage of dynamically reacting molecules only slightly depends on the depth of the intermediate well but rather on Delta Delta G double dagger of the initial and the follow-up transition states.

  DOI：

  10.1021/jo500035b