(S)-5-[(R,Z)-3-(2,5-dimethoxy-4-methylphenyl)but-1-enyl]-2,2,4,4-tetramethyl-1,3-dioxolane | 1346677-59-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: (S)-5-[(R,Z)-3-(2,5-dimethoxy-4-methylphenyl)but-1-enyl]-2,2,4,4-tetramethyl-1,3-dioxolane
• CAS: 1346677-59-5
• 化学式: C₂₀H₃₀O₄
• 分子量: 334.456
• InChiKey: UWZGFMPWCSDTDB-OCEKKPHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  2-(2,5-dimethoxy-4-methylphenyl)-3-(tosyloxy)propyl acetate 在 sodium tetrahydroborate 、 hexaammonium heptamolybdate tetrahydrate 、 偶氮二甲酸二异丙酯 、 双氧水 、 sodium hexamethyldisilazane 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 、 水 、 二甲基亚砜 为溶剂， 反应 12.25h， 生成 (S)-5-[(R,Z)-3-(2,5-dimethoxy-4-methylphenyl)but-1-enyl]-2,2,4,4-tetramethyl-1,3-dioxolane 、 (S)-5-[(R,E)-3-(2,5-dimethoxy-4-methylphenyl)but-1-enyl]-2,2,4,4-tetramethyl-1,3-dioxolane
  参考文献：
  名称：

  Enantioselective syntheses of the assigned structures of the helibisabonols A and B

  摘要：

  The enantioselective syntheses of the compounds with the assigned structures of the helibisabonols A and B have been accomplished. Using an enzymatic desymmetrization of the sigma-symmetrical diol (route a) and a diastereoselective conjugate addition of the methyl to the enone with a chiral auxiliary (route b) we constructed the key tertiary stereogenic center at the benzylic position (C7) and then used an asymmetric dihydroxylation for assembling the C10 stereogenic center. In addition, possible diastereoisomers of the natural products were prepared and detailed comparisons of the H-1 and C-13 NMR spectra were conducted. As a result, the structure originally assigned to helibisabonol A may be revised to (7R,10R)-1. In the case of helibisabonol B, the (7R,10R)-2 would be reasonable based on a comparison of the NMR data and the biogenetic parallelism with helibisabonol A. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.03.064