(1R,3R,4S)-8-phenyl-p-menthan-3-yl (2'S)-fluoro-3'-(p-methoxybenzyloxy)-2'-methylpropionate | 165449-18-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R,3R,4S)-8-phenyl-p-menthan-3-yl (2'S)-fluoro-3'-(p-methoxybenzyloxy)-2'-methylpropionate
• CAS: 165449-18-3
• 化学式: C₂₈H₃₇FO₄
• 分子量: 456.598
• InChiKey: JEKVTYPAMZXIOM-PFCXFHTISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.27
• 重原子数：
  33.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1R,3R,4S)-8-phenyl-p-menthan-3-yl (2'S)-fluoro-3'-(p-methoxybenzyloxy)-2'-methylpropionate 在 18-冠醚-6 、 三乙胺 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  Enantiocontrolled synthesis of chiral propane-1,3-diol derivatives possessing fluorinated quaternary stereogenic centers

  摘要：

  A general method for the preparation of chiral propane-1,3-diol derivatives possessing fluorinated quaternary stereogenic centers was established as follows. The diastereoselective alkylation of (1R,3R,4S)-8-phenylmenthyl hydrogen fluoromalonate 9, followed by the reduction of the resulting carboxylic acids 10 - 13 in two steps, provided the alcohols 14 - 17. After protection of the hydroxyl group with p-methoxybenzyl group, the phenylmenthyl esters 21 - 24 were converted into chiral propane-1,3-diols 25 and 30 - 32 via the acids 29.

  DOI：

  10.1016/0957-4166(94)80054-5
• 作为产物：
  描述：

  2-Chlorocarbonyl-2-fluoro-propionic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 在 三氟甲磺酸 、 tetrabutylammonium borohydride 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (1R,3R,4S)-8-phenyl-p-menthan-3-yl (2'S)-fluoro-3'-(p-methoxybenzyloxy)-2'-methylpropionate
  参考文献：
  名称：

  Enantiocontrolled synthesis of chiral propane-1,3-diol derivatives possessing fluorinated quaternary stereogenic centers

  摘要：

  A general method for the preparation of chiral propane-1,3-diol derivatives possessing fluorinated quaternary stereogenic centers was established as follows. The diastereoselective alkylation of (1R,3R,4S)-8-phenylmenthyl hydrogen fluoromalonate 9, followed by the reduction of the resulting carboxylic acids 10 - 13 in two steps, provided the alcohols 14 - 17. After protection of the hydroxyl group with p-methoxybenzyl group, the phenylmenthyl esters 21 - 24 were converted into chiral propane-1,3-diols 25 and 30 - 32 via the acids 29.

  DOI：

  10.1016/0957-4166(94)80054-5