(-)-(2R,3'E)-2-methoxy-2-(3'-pentenyl)-tetrahydropyran-4-one | 168842-05-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (-)-(2R,3'E)-2-methoxy-2-(3'-pentenyl)-tetrahydropyran-4-one
• 英文别名: (2R)-2-methoxy-2-[(E)-pent-3-enyl]oxan-4-one
• CAS: 168842-05-5
• 化学式: C₁₁H₁₈O₃
• 分子量: 198.262
• InChiKey: QTWKWQRUYRUEDU-PGLGOXFNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  丙基氯化镁 、 (-)-(2R,3'E)-2-methoxy-2-(3'-pentenyl)-tetrahydropyran-4-one 以 四氢呋喃 为溶剂， 反应 4.0h， 以66%的产率得到(-)-(2R,4S,3'E)-4-hydroxy-2-methoxy-2-(3'-pentenyl)-4-propyl-tetrahydropyran
  参考文献：
  名称：

  Chiral building blocks from streptomyces-2.1 stereoselective transformation of streptenol a into 3-methyl-δ-lactones

  摘要：

  The stereoselective synthesis of both enantiomeric forms of 3-alkyl-streptenols A 7-9 and ent-7-9 in four steps is described. Hereby, the stereoselective acetalization to the pyrans 2a and 2b directed by the solvent and the catalyst used was a key step in the reaction sequence. The 3-alkyl-streptenols represents interesting chiral building blocks which can be used for the synthesis of analogues of HMG-CoA inhibitors, e.g. 3-methyl-delta-lactones.

  DOI：

  10.1016/0040-4020(95)00438-e
• 作为产物：
  描述：

  (-)-(2R,4S)-4-hydroxy-2-methoxy-2-(9E-pentenyl)-tetrahydropyran 在 tris(triphenylphosphine)ruthenium(II) chloride 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以92%的产率得到(-)-(2R,3'E)-2-methoxy-2-(3'-pentenyl)-tetrahydropyran-4-one
  参考文献：
  名称：

  Chiral building blocks from streptomyces-2.1 stereoselective transformation of streptenol a into 3-methyl-δ-lactones

  摘要：

  The stereoselective synthesis of both enantiomeric forms of 3-alkyl-streptenols A 7-9 and ent-7-9 in four steps is described. Hereby, the stereoselective acetalization to the pyrans 2a and 2b directed by the solvent and the catalyst used was a key step in the reaction sequence. The 3-alkyl-streptenols represents interesting chiral building blocks which can be used for the synthesis of analogues of HMG-CoA inhibitors, e.g. 3-methyl-delta-lactones.

  DOI：

  10.1016/0040-4020(95)00438-e

文献信息

• Chiral building blocks from streptomyces-2.1 stereoselective transformation of streptenol a into 3-methyl-δ-lactones
  作者：Joachim Adam、Robert Klein、Susanne Grabley、Peter Hammann

  DOI：10.1016/0040-4020(95)00438-e

  日期：1995.7

  The stereoselective synthesis of both enantiomeric forms of 3-alkyl-streptenols A 7-9 and ent-7-9 in four steps is described. Hereby, the stereoselective acetalization to the pyrans 2a and 2b directed by the solvent and the catalyst used was a key step in the reaction sequence. The 3-alkyl-streptenols represents interesting chiral building blocks which can be used for the synthesis of analogues of HMG-CoA inhibitors, e.g. 3-methyl-delta-lactones.