methyl 2,6-dimethyl-2-(tetrahydropyranyloxy)hept-6-enoate | 131490-02-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 2,6-dimethyl-2-(tetrahydropyranyloxy)hept-6-enoate
• 英文别名: methyl (2R)-2,6-dimethyl-2-[(2S)-oxan-2-yl]oxyhept-6-enoate
• CAS: 131490-02-3
• 化学式: C₁₅H₂₆O₄
• 分子量: 270.369
• InChiKey: GUFXHBNKRWHDMA-DZGCQCFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.21
• 重原子数：
  19.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  methyl 2,6-dimethyl-2-(tetrahydropyranyloxy)hept-6-enoate 在 盐酸 、 lithium aluminium tetrahydride 作用下， 以 甲醇 、 乙醚 、 水 为溶剂， 生成 (2R)-(-)-2,6-dimethyl-6-heptene-1,2-diol
  参考文献：
  名称：

  Enantiomerically pure acetals in organic synthesis. 2. Diastereoselective alkylation of enantiomeric lithio alkyl lactyl tetrahydropyranosides and related enolates

  摘要：

  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.

  DOI：

  10.1021/jo00003a035
• 作为产物：
  描述：

  4-methyl-4-pentenyl-1-tosylate 在 六甲基磷酰三胺 、 sodium iodide 、 lithium diisopropyl amide 作用下， 以 丙酮 为溶剂， 反应 1.77h， 生成 methyl 2,6-dimethyl-2-(tetrahydropyranyloxy)hept-6-enoate
  参考文献：
  名称：

  Enantiomerically pure acetals in organic synthesis. 2. Diastereoselective alkylation of enantiomeric lithio alkyl lactyl tetrahydropyranosides and related enolates

  摘要：

  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.

  DOI：

  10.1021/jo00003a035

文献信息

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

  DOI：——

  日期：——