5-[(2S,3S)-3-propan-2-yloxiran-2-yl]pentan-2-one | 133909-64-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-[(2S,3S)-3-propan-2-yloxiran-2-yl]pentan-2-one
• CAS: 133909-64-5
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: IRCRWGGUBXMAJG-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  29.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-[(2S,3S)-3-propan-2-yloxiran-2-yl]pentan-2-one 在 三氟甲磺酸三甲基硅酯 、 三苯基硅烷 作用下， 生成 rel-(1R,5S,7S)-5-methyl-7-(1-methylethyl)-6,8-dioxabicyclo<3.2.1>octane
  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
• 作为产物：
  描述：

  2-methyl-2-(3-bromopropyl)-5,5-dimethyl-1,3-dioxane 在 lithium amide 、 oxonium 、 氨 、 lithium 、 间氯过氧苯甲酸 作用下， 以 乙醚 为溶剂， 生成 5-[(2S,3S)-3-propan-2-yloxiran-2-yl]pentan-2-one
  参考文献：
  名称：

  6,8-二氧杂双环[3.2.1]辛烷的不寻常缩醛裂解中的氧杂环丁烷

  摘要：

  用BF 3 ·OEt 2和TMSCN处理后，环氧酮1环化成双环缩醛2，然后裂解产生环氧丙烷5，为单一立体异构体。5的还原性脱氰作用导致产生环氧丙烷7，环氧丙烷7是天然产品短毒素家族中的一个结构单元。研究了该反应顺序的范围和局限性。

  DOI：

  10.1016/0040-4039(95)02167-1

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.
• Oxepanes from an unusual acetal cleavage of 6,8-dioxabicyclo[3.2.1]octanes
  作者：Scott D. Rychnovsky、Vilas H. Dahanukar

  DOI：10.1016/0040-4039(95)02167-1

  日期：1996.1

  On treatment with BF3·OEt2 and TMSCN, epoxy ketone 1 cyclized to the bicyclic acetal 2, which then cleaved to give primarily the oxepane 5 as a single stereoisomer. Reductive decyanation of 5 led to the oxepane 7, a structural unit present in the brevetoxin family of natural products. The scope and limitations of this reaction sequence were investigated.

  用BF 3 ·OEt 2和TMSCN处理后，环氧酮1环化成双环缩醛2，然后裂解产生环氧丙烷5，为单一立体异构体。5的还原性脱氰作用导致产生环氧丙烷7，环氧丙烷7是天然产品短毒素家族中的一个结构单元。研究了该反应顺序的范围和局限性。