(1R,3R,4S)-8-phenyl-p-menthan-3-yl (2'S)-2'benzyl-2'-fluoro-3'-(p-methoxybenzyloxy)propionate | 165449-25-2

• 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)-2'benzyl-2'-fluoro-3'-(p-methoxybenzyloxy)propionate
• 英文别名: [(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl] (2S)-2-benzyl-2-fluoro-3-[(4-methoxyphenyl)methoxy]propanoate
• CAS: 165449-25-2
• 化学式: C₃₄H₄₁FO₄
• 分子量: 532.696
• InChiKey: IOTHOMVKKUTXAR-JYVJMKIYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  39
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R,3R,4S)-8-phenyl-p-menthan-3-yl (2'S)-2'benzyl-2'-fluoro-3'-(p-methoxybenzyloxy)propionate 在 sodium tetrahydroborate 、 18-冠醚-6 、 三乙胺 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 7.0h， 生成 (2R)-2-benzyl-2-fluoro-3-(p-methoxybenzyloxy)-1-propanol
  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-Benzyl-2-fluoro-malonic acid mono-[(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl] ester 在 草酰氯 、 三氟甲磺酸 、 tetrabutylammonium borohydride 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 (1R,3R,4S)-8-phenyl-p-menthan-3-yl (2'S)-2'benzyl-2'-fluoro-3'-(p-methoxybenzyloxy)propionate
  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

文献信息

• Enantiocontrolled synthesis of chiral propane-1,3-diol derivatives possessing fluorinated quaternary stereogenic centers
  作者：Masataka Ihara、Tatsuo Kawabuchi、Yuji Tokunaga、Keiichiro Fukumoto

  DOI：10.1016/0957-4166(94)80054-5

  日期：1994.6

  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.