1-(3-Methyl-2,3-dihydro-furo[2,3-c]pyridin-5-yl)-ethanol | 185220-94-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(3-Methyl-2,3-dihydro-furo[2,3-c]pyridin-5-yl)-ethanol
• 英文别名: 1-(3-Methyl-2,3-dihydrofuro[2,3-c]pyridin-5-yl)ethanol
• CAS: 185220-94-4
• 化学式: C₁₀H₁₃NO₂
• 分子量: 179.219
• InChiKey: XUEBKWAOGVQQKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  42.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(3-Methyl-2,3-dihydro-furo[2,3-c]pyridin-5-yl)-ethanol 在 吡啶 、 sodium hydroxide 、 Porcine pancreatic lipase type II 、 四氯苯醌 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 194.0h， 生成 (R)-1-(3-Methyl-furo[2,3-c]pyridin-5-yl)-ethanol
  参考文献：
  名称：

  Stereoselective Synthesis of Furo[2,3-c]pyridine Pyrimidine Thioethers, A New Class of Potent HIV-1 Non-nucleoside Reverse Transcriptase Inhibitors

  摘要：

  An efficient stereoselective total synthesis of the furo[2,3-c]pyridine thiopyrimidine HIV-1 reverse transcriptase inhibitors, PNU-142721 and PNU-109886, has been developed. A convergent approach was utilized, providing direct access to the desired (S)-configuration of the molecule by making use of the alkylation of 4-amino-6-chloro-2-thiopyrimidine with the appropriate (R)-1-chloroethyl furo[2,3-c]pyridine intermediates. The successful preparation makes use of an efficient enzymatic kinetic resolution of the key 1-hydroxyethyl furo[2,3-c]pyridine intermediates to establish stereochemical control of the respective stereogenic centers. In addition, a workable asymmetric reduction strategy was developed for the synthesis of PNU-109886. Prudent reagent selection for the chlorination required for the final coupling reactions allowed for maintenance of the stereochemical integrity of the target compounds. Structural assignment of the absolute configuration of PNU-142721 and PNU-109886 as the (S)-enantiomer was confirmed by X-ray crystallographic analysis.

  DOI：

  10.1021/jo9810359
• 作为产物：
  描述：

  2-氯-3-羟基-6-碘吡啶 在 palladium hydroxide - carbon sodium hydroxide 、 正丁基锂 、 偶氮二异丁腈 、 氢气 、 碘 、 三正丁基氢锡 、 lithium hydride 、 sodium hydride 、 potassium carbonate 作用下， 以 乙醇 、 水 、 苯 为溶剂， -78.0~45.0 ℃ 、151.68 kPa 条件下， 反应 35.0h， 生成 1-(3-Methyl-2,3-dihydro-furo[2,3-c]pyridin-5-yl)-ethanol
  参考文献：
  名称：

  Stereoselective Synthesis of Furo[2,3-c]pyridine Pyrimidine Thioethers, A New Class of Potent HIV-1 Non-nucleoside Reverse Transcriptase Inhibitors

  摘要：

  An efficient stereoselective total synthesis of the furo[2,3-c]pyridine thiopyrimidine HIV-1 reverse transcriptase inhibitors, PNU-142721 and PNU-109886, has been developed. A convergent approach was utilized, providing direct access to the desired (S)-configuration of the molecule by making use of the alkylation of 4-amino-6-chloro-2-thiopyrimidine with the appropriate (R)-1-chloroethyl furo[2,3-c]pyridine intermediates. The successful preparation makes use of an efficient enzymatic kinetic resolution of the key 1-hydroxyethyl furo[2,3-c]pyridine intermediates to establish stereochemical control of the respective stereogenic centers. In addition, a workable asymmetric reduction strategy was developed for the synthesis of PNU-109886. Prudent reagent selection for the chlorination required for the final coupling reactions allowed for maintenance of the stereochemical integrity of the target compounds. Structural assignment of the absolute configuration of PNU-142721 and PNU-109886 as the (S)-enantiomer was confirmed by X-ray crystallographic analysis.

  DOI：

  10.1021/jo9810359