rel-(2R,3S,6S)-6-methyl-6-(2-propenyl)-2-(1-methylethyl)tetrahydro-2H-pyran-3-ol | 133909-70-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: rel-(2R,3S,6S)-6-methyl-6-(2-propenyl)-2-(1-methylethyl)tetrahydro-2H-pyran-3-ol
• 英文别名: (2R,3S,6S)-6-methyl-2-propan-2-yl-6-prop-2-enyloxan-3-ol
• CAS: 133909-70-3
• 化学式: C₁₂H₂₂O₂
• 分子量: 198.305
• InChiKey: IYXLJWRQZNGBPH-QJPTWQEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-((2S,3S)-3-Isopropyl-oxiranyl)-butan-2-one 、 烯丙基三甲基硅烷 在 三氟甲磺酸三甲基硅酯 作用下， 生成 rel-(2R,3S,6S)-6-methyl-6-(2-propenyl)-2-(1-methylethyl)tetrahydro-2H-pyran-3-ol 、 rel-(2R,5S,αS)-5-methyl-5-(2-propenyl)-α-(1-methylethyl)tetrahydrofuran-2-methanol 、 (S)-1-((2R,5S)-5-Allyl-5-methyl-tetrahydro-furan-2-yl)-2-methyl-propan-1-ol
  参考文献：
  名称：

  Stereochemical control in reactions of nucleophiles with oxocarbenium ions formed by intramolecular opening of activated epoxides by neighboring carbonyl groups

  摘要：

  Tandem cyclization/reduction and cyclization/alkylation processes for the stereoselective synthesis of 2,5-disubstituted tetrahydrofurans, 2,6-disubstituted tetrahydropyrans, and 2,7-disubstituted oxepanes are described. In the presence of Lewis acids or TMSOTf, gamma,delta-, delta,epsilon- and epsilon,zeta-epoxy ketones and esters undergo cyclization to the corresponding oxocarbenium ions, which react in situ with a variety of organosilanes and organoaluminum reagents to give the substituted oxacyclic products. For the synthesis of substituted tetrahydrofurans, the stereochemical control of the addition process was much higher with TMSOTf than BF3.OEt2.

  DOI：

  10.1021/jo00013a013

文献信息

• Stereochemical control in reactions of nucleophiles with oxocarbenium ions formed by intramolecular opening of activated epoxides by neighboring carbonyl groups
  作者：Christopher H. Fotsch、A. Richard Chamberlin

  DOI：10.1021/jo00013a013

  日期：1991.6

  Tandem cyclization/reduction and cyclization/alkylation processes for the stereoselective synthesis of 2,5-disubstituted tetrahydrofurans, 2,6-disubstituted tetrahydropyrans, and 2,7-disubstituted oxepanes are described. In the presence of Lewis acids or TMSOTf, gamma,delta-, delta,epsilon- and epsilon,zeta-epoxy ketones and esters undergo cyclization to the corresponding oxocarbenium ions, which react in situ with a variety of organosilanes and organoaluminum reagents to give the substituted oxacyclic products. For the synthesis of substituted tetrahydrofurans, the stereochemical control of the addition process was much higher with TMSOTf than BF3.OEt2.