2-{[(R)-[(4R)-2,2-dimethyl-[1,3]dioxolan-4-yl]-(4-methoxyphenyl)methyl]oxy}-(1S)-1-(2-fluorophenyl)-1-(4-fluorophenyl)ethanol | 1053246-09-5

• 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}-(1S)-1-(2-fluorophenyl)-1-(4-fluorophenyl)ethanol
• 英文别名: (1S)-2-[(R)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-(4-methoxyphenyl)methoxy]-1-(2-fluorophenyl)-1-(4-fluorophenyl)ethanol
• CAS: 1053246-09-5
• 化学式: C₂₇H₂₈F₂O₅
• 分子量: 470.513
• InChiKey: LLXQNZZAHJGMOC-SLQPCKNISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  7

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}-(1S)-1-(2-fluorophenyl)-1-(4-fluorophenyl)ethanol 在 三甲基氯化锡 、 sodium iodide 、 tin(ll) chloride 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以75%的产率得到(S)-1-(2-fluorophenyl)-1-(4-fluorophenyl)ethane-1,2-diol
  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-{[(R)-[(4R)-2,2-dimethyl-[1,3]dioxolan-4-yl]-(4-methoxyphenyl)methyl]oxy}-1-(2-fluorophenyl)ethan-1-one 、 4-氟苯基溴化镁 在 magnesium bromide 作用下， 以 二氯甲烷 为溶剂， 以97%的产率得到2-{[(R)-[(4R)-2,2-dimethyl-[1,3]dioxolan-4-yl]-(4-methoxyphenyl)methyl]oxy}-(1S)-1-(2-fluorophenyl)-1-(4-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