1-(3',4',5'-trimethoxyphenyl)-2-pentyn-1-ol | 1060671-08-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(3',4',5'-trimethoxyphenyl)-2-pentyn-1-ol
• CAS: 1060671-08-0
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: QQHSTRBOEHGWPH-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.16
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  47.92
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  dicobalt octacarbonyl 、 1-(3',4',5'-trimethoxyphenyl)-2-pentyn-1-ol 以 乙醚 为溶剂， 生成
  参考文献：
  名称：

  Intramolecular Cyclizations of Co₂(CO)₆-Complexed Propargyl Radicals: Synthesis of d,l- and meso-1,5-Cyclodecadiynes

  摘要：

  Intramolecular radical cyclizations of Co-2(CO)(6)-complexed bis-propargyl alcohols 1-5 provide an easy, two-step access to the otherwise hardly accessible d,l- and meso-3,4-diaryl-1,5-cyclodecadiynes 21-25. The acid-induced generation of bis-cations 6-10 is followed by reduction with a 100-fold excess of zinc, generating key reactive intermediates, i.e. the cobalt-complexed bis-propargyl radicals 11-15. The substitution pattern (0-, 4-, 3,4-, 3,4,5-) and the nature of aromatic substituents (H, i-Pr, OMe) are found essential both to the diastereoselectivity of the process-with d,l:meso ratios varying from 54:46 to 80:20-and the isolability of individual stereoisomers. In particular, an accumulation of methoxy groups on the periphery of the aromatic rings facilitates separation in both intra- and intermolecular reactions. The observed disparity in the level of diastereoselection in intra- and intermolecular reactions is accounted for on the basis of conformational analysis, calculation data for cobalt-complexed propargyl radicals, and the concept of a CH/pi coordination. The new knowledge thus acquired has a predicting power, allowing future substrates to be designed, both topologically and stereoelectronically, in a manner favoring either d,l or meso diastereomers.

  DOI：

  10.1021/om7010497