methyl 2-methyl-3-phenyl-2-(tetrahydropyranyloxy)propanoate | 131489-98-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: methyl 2-methyl-3-phenyl-2-(tetrahydropyranyloxy)propanoate
• 英文别名: methyl (2R)-2-methyl-2-[(2R)-oxan-2-yl]oxy-3-phenylpropanoate
• CAS: 131489-98-0
• 化学式: C₁₆H₂₂O₄
• 分子量: 278.348
• InChiKey: RKWKTYTXUYEQNZ-GDBMZVCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  lithium;(2R)-oxan-2-olate 、 溴甲苯 生成 methyl 2-methyl-3-phenyl-2-(tetrahydropyranyloxy)propanoate
  参考文献：
  名称：

  MASH, EUGENE A.;FRYLING, JAMES A., J. ORG. CHEM., 56,(1991) N, C. 1094-1098

  摘要：

  DOI：

文献信息

• Enantiomerically pure acetals in organic synthesis. 2. Diastereoselective alkylation of enantiomeric lithio alkyl lactyl tetrahydropyranosides and related enolates
  作者：Eugene A. Mash、James A. Fryling

  DOI：10.1021/jo00003a035

  日期：1991.2

  A concise approach for the rapid synthesis of enantiomerically pure alpha-alkylated derivatives of lactate esters and of other enantiomerically pure alpha-hydroxy esters is presented. This methodology, which makes use of enantiomeric lithium enolates prepared from diastereomeric tetrahydropyranyl ethers derived from alkyl lactates and other alpha-hydroxy esters, is used to prepare both enantiomers of frontalin from (S)-(-)-methyl lactate.