(4R,6S)-4,6-dimethyl-2-<(2S)-2-methyl-3-(tert-butoxy)-propyl>-3,4-dihydro-2H-pyran | 146308-13-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R,6S)-4,6-dimethyl-2-<(2S)-2-methyl-3-(tert-butoxy)-propyl>-3,4-dihydro-2H-pyran
• 英文别名: (2S,4R)-2,4-dimethyl-6-[(2S)-2-methyl-3-[(2-methylpropan-2-yl)oxy]propyl]-3,4-dihydro-2H-pyran
• CAS: 146308-13-6
• 化学式: C₁₅H₂₈O₂
• 分子量: 240.386
• InChiKey: GGWJJNQTFXCSFH-AGIUHOORSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  甲基溴化镁 、 (4R,6S)-4,6-dimethyl-2-<(2S)-2-methyl-3-(tert-butoxy)-propyl>-3,4-dihydro-2H-pyran 在 bis(triphenylphosphine)nickel(II) chloride 作用下， 生成 (E)-(2S,4R,8S)-9-(tert-butoxy)-4,6,8-trimethylnon-5-en-2-ol
  参考文献：
  名称：

  A stereoselective synthesis of trisubstituted alkenes. Part 2. The nickel-catalysed coupling of Grignard reagents with 6-alkyl-3,4-dihydro-2H-pyrans and acyclic enol ethers

  摘要：

  The Ni0-catalysed coupling of Grignard reagents devoid of beta-hydrogens with 6-alkyl-3,4-dihydro-2H-pyrans and acyclic enol ethers is highly stereoselective and gives trisubstituted alkenes with retention of configuration. The reaction was applied to syntheses of the aggregation pheromone of the square-necked grain beetle, a fragment of Premonensin B, and the polyketide fragment of Jaspamide.

  DOI：

  10.1039/p19920003431
• 作为产物：
  描述：

  (4R,6S)-4,6-dimethyltetrahydropyran-2-one 在 盐酸 、 sodium hydroxide 、 二异丁基氢化铝 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 16.17h， 生成 (4R,6S)-4,6-dimethyl-2-<(2S)-2-methyl-3-(tert-butoxy)-propyl>-3,4-dihydro-2H-pyran
  参考文献：
  名称：

  A stereoselective synthesis of trisubstituted alkenes. Part 2. The nickel-catalysed coupling of Grignard reagents with 6-alkyl-3,4-dihydro-2H-pyrans and acyclic enol ethers

  摘要：

  The Ni0-catalysed coupling of Grignard reagents devoid of beta-hydrogens with 6-alkyl-3,4-dihydro-2H-pyrans and acyclic enol ethers is highly stereoselective and gives trisubstituted alkenes with retention of configuration. The reaction was applied to syntheses of the aggregation pheromone of the square-necked grain beetle, a fragment of Premonensin B, and the polyketide fragment of Jaspamide.

  DOI：

  10.1039/p19920003431

文献信息

• A stereoselective synthesis of trisubstituted alkenes. Part 2. The nickel-catalysed coupling of Grignard reagents with 6-alkyl-3,4-dihydro-2H-pyrans and acyclic enol ethers
  作者：Philip A. Ashworth、Nicholas J. Dixon、Philip J. Kocieński、Sjoerd N. Wadman

  DOI：10.1039/p19920003431

  日期：——

  The Ni0-catalysed coupling of Grignard reagents devoid of beta-hydrogens with 6-alkyl-3,4-dihydro-2H-pyrans and acyclic enol ethers is highly stereoselective and gives trisubstituted alkenes with retention of configuration. The reaction was applied to syntheses of the aggregation pheromone of the square-necked grain beetle, a fragment of Premonensin B, and the polyketide fragment of Jaspamide.