2-{[(R)-[(4R)-2,2-dimethyl-[1,3]dioxolan-4-yl]-(4-methoxyphenyl)methyl]oxy}-1-(2-fluorophenyl)ethanol | 1053246-05-1

• 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: 2-{[(R)-[(4R)-2,2-dimethyl-[1,3]dioxolan-4-yl]-(4-methoxyphenyl)methyl]oxy}-1-(2-fluorophenyl)ethanol
• 英文别名: 2-[(R)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-(4-methoxyphenyl)methoxy]-1-(2-fluorophenyl)ethanol
• CAS: 1053246-05-1
• 化学式: C₂₁H₂₅FO₅
• 分子量: 376.425
• InChiKey: BAFMWKDEJNYBJR-FXJNCMGBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-{[(R)-[(4R)-2,2-dimethyl-[1,3]dioxolan-4-yl]-(4-methoxyphenyl)methyl]oxy}-1-(2-fluorophenyl)ethanol 在 N-甲基吲哚酮 、 四丙基高钌酸铵 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以65%的产率得到2-{[(R)-[(4R)-2,2-dimethyl-[1,3]dioxolan-4-yl]-(4-methoxyphenyl)methyl]oxy}-1-(2-fluorophenyl)ethan-1-one
  参考文献：
  名称：

  Stereoselective synthesis of (+)-flutriafol

  摘要：

  The stereoselective synthesis of (+)-flutriafol, a triazole fungicide, has been accomplished in seven linear steps from (1S)-[(4R)-2,2-dimethyl-[1,3]-dioxotan-4-yl]-(4-methoxyphenyl)methanol in 15% overall yield. Diastereoselective nucleophilic 1,2-addition was employed as a key step for constructing the requisite chiral 1,2-diol for flutriafol. A high degree of 1,4-asymmetric induction could be realized via a chelation-controlled mechanism during the key alkylation step. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.06.007
• 作为产物：
  描述：

  2-(2-fluorophenyl)oxirane 、 (2R,3R)-3-hydroxy-1,2-O-isopropylidene-3-p-methoxyphenyl-1,2-propanediol 在 potassium hydride 、 18-冠醚-6 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 以53%的产率得到2-{[(R)-[(4R)-2,2-dimethyl-[1,3]dioxolan-4-yl]-(4-methoxyphenyl)methyl]oxy}-1-(2-fluorophenyl)ethanol
  参考文献：
  名称：

  Stereoselective synthesis of (+)-flutriafol

  摘要：

  The stereoselective synthesis of (+)-flutriafol, a triazole fungicide, has been accomplished in seven linear steps from (1S)-[(4R)-2,2-dimethyl-[1,3]-dioxotan-4-yl]-(4-methoxyphenyl)methanol in 15% overall yield. Diastereoselective nucleophilic 1,2-addition was employed as a key step for constructing the requisite chiral 1,2-diol for flutriafol. A high degree of 1,4-asymmetric induction could be realized via a chelation-controlled mechanism during the key alkylation step. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.06.007