(R)-7-methyl-3-(4-methylphenyl)-1-phenyl-oct-6-en-1-yn-3-ol | 1383540-95-1

• 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: (R)-7-methyl-3-(4-methylphenyl)-1-phenyl-oct-6-en-1-yn-3-ol
• 英文别名: (3R)-7-methyl-3-(4-methylphenyl)-1-phenyloct-6-en-1-yn-3-ol
• CAS: 1383540-95-1
• 化学式: C₂₂H₂₄O
• 分子量: 304.432
• InChiKey: ZCUSBWHWZBYOQM-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (4-甲基苯基)吗啉-4-基甲酮 在 萘 、 Dimethylzinc 、 lithium 、 copper(II) bis(trifluoromethanesulfonate) 、 C-((1S,2R,4R)-2-Hydroxy-7,7-dimethyl-bicyclo[2.2.1]hept-1-yl)-N-naphthalen-1-ylmethyl-methanesulfonamide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 339.5h， 生成 (R)-7-methyl-3-(4-methylphenyl)-1-phenyl-oct-6-en-1-yn-3-ol 、 (S)-7-methyl-3-(4-methylphenyl)-1-phenyl-oct-6-en-1-yn-3-ol
  参考文献：
  名称：

  Enantioselective synthesis of (+)-gossonorol and related systems using organozinc reagents

  摘要：

  The sesquiterpene (+)-gossonorol is prepared in only three synthetic steps in 60% overall yield and 82% ee from commercially available reagents. The key asymmetric step is the catalytic enantioselective addition of dimethylzinc to 5-methyl-1-(2-methylphenyl)hex-4-en-1-one catalyzed by chiral isoborneolsulfonamide ligands in the presence of titanium tetraisopropoxide. The modular approach allows the synthesis not only of the aforementioned natural product but also other products arising from the corresponding processes of ethylation, phenylation, and ethynylation, just by changing the final nucleophilic reagent and using the same isoborneol type ligand. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.04.003

文献信息

• Enantioselective synthesis of (+)-gossonorol and related systems using organozinc reagents
  作者：Susana González-López、Miguel Yus、Diego J. Ramón

  DOI：10.1016/j.tetasy.2012.04.003

  日期：2012.4

  The sesquiterpene (+)-gossonorol is prepared in only three synthetic steps in 60% overall yield and 82% ee from commercially available reagents. The key asymmetric step is the catalytic enantioselective addition of dimethylzinc to 5-methyl-1-(2-methylphenyl)hex-4-en-1-one catalyzed by chiral isoborneolsulfonamide ligands in the presence of titanium tetraisopropoxide. The modular approach allows the synthesis not only of the aforementioned natural product but also other products arising from the corresponding processes of ethylation, phenylation, and ethynylation, just by changing the final nucleophilic reagent and using the same isoborneol type ligand. (C) 2012 Elsevier Ltd. All rights reserved.