7-(4-pentylphenyl)-3-phenylhepta-1,6-diyn-3-yl benzoate | 1435518-44-7

• 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: 7-(4-pentylphenyl)-3-phenylhepta-1,6-diyn-3-yl benzoate
• CAS: 1435518-44-7
• 化学式: C₃₁H₃₀O₂
• 分子量: 434.578
• InChiKey: VOHCDGWCCTUBAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.94
• 重原子数：
  33.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 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：

  7-(4-pentylphenyl)-3-phenylhepta-1,6-diyn-3-yl benzoate 在 (acetonitrile)[(2',4',6'-triisopropyl-3,4,5,6-tetramethyl-1,1'-biphenyl-2-yl)di-tert-butylphosphine]gold(I) hexafluoroantimonate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以81%的产率得到6-pentyl-3-phenyl-2,4a-dihydro-1H-fluoren-4-yl benzoate
  参考文献：
  名称：

  Gold-Catalyzed Cycloisomerization of 1,6-Diyne Carbonates and Esters to 2,4a-Dihydro-1H-fluorenes

  摘要：

  A synthetic method to prepare 2,4a-dihydro-1H-fluorenes efficiently from gold(I)-catalyzed 1,2-acyloxy migration/cyclopropenation/Nazarov cyclization of 1,6-diyne carbonates and esters is described. The suggested reaction pathway provides rare examples of [2,3]-sigmatropic rearrangement in this class of compounds as well as the involvement of an in situ formed cyclopropene intermediate in gold catalysis. Experimental and ONIOM(QM:QM') [our own n-layered integrated molecular orbital and molecular mechanics(quantum mechanics quantum mechanics')] computational studies based on the proposed Au carbenoid species provide insight into this unique selectivity.

  DOI：

  10.1021/ja4032727
• 作为产物：
  描述：

  5-(4-pentylphenyl)-1-phenylpent-4-yn-1-one 在 正丁基锂 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 环己烷 为溶剂， 反应 5.83h， 生成 7-(4-pentylphenyl)-3-phenylhepta-1,6-diyn-3-yl benzoate
  参考文献：
  名称：

  Gold-Catalyzed Cycloisomerization of 1,6-Diyne Carbonates and Esters to 2,4a-Dihydro-1H-fluorenes

  摘要：

  A synthetic method to prepare 2,4a-dihydro-1H-fluorenes efficiently from gold(I)-catalyzed 1,2-acyloxy migration/cyclopropenation/Nazarov cyclization of 1,6-diyne carbonates and esters is described. The suggested reaction pathway provides rare examples of [2,3]-sigmatropic rearrangement in this class of compounds as well as the involvement of an in situ formed cyclopropene intermediate in gold catalysis. Experimental and ONIOM(QM:QM') [our own n-layered integrated molecular orbital and molecular mechanics(quantum mechanics quantum mechanics')] computational studies based on the proposed Au carbenoid species provide insight into this unique selectivity.

  DOI：

  10.1021/ja4032727