2,2-dibutyl-1,4-dioxaspiro<2.2>pentane | 113403-67-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: 2,2-dibutyl-1,4-dioxaspiro<2.2>pentane
• 英文别名: 2,2-Dibutyl-1,4-dioxaspiro[2.2]pentane
• CAS: 113403-67-1
• 化学式: C₁₁H₂₀O₂
• 分子量: 184.279
• InChiKey: YXBPAWDTWSKMFY-UHFFFAOYSA-N

物化性质

• 沸点：
  210.2±8.0 °C(Predicted)
• 密度：
  0.98±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  25.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2-dibutyl-1,4-dioxaspiro<2.2>pentane 、 二乙胺 以 丙酮 为溶剂， 反应 0.5h， 以76%的产率得到3-butyl-1-(diethylamino)-3-hydroxyheptan-2-one
  参考文献：
  名称：

  1,4-Dioxaspiro[2.2]pentanes. Synthesis, spectroscopic properties, and reactions with nucleophiles

  摘要：

  A number of simple allenes have been converted cleanly to the corresponding 1,4-dioxaspiro[2.2]pentanes in good yields by oxidation with dimethyldioxirane. Mono- and trisubstituted allenes give the anti diastereomers with good stereoselectivity, whereas 1,3-disubstituted allenes show only a slight preference for the anti,anti isomers, unless steric effects are extreme. Stereochemical assignments are based on steric considerations and a consistent set of NMR characteristics that permit structural attributions. The addition of a range of nucleophiles (water, alcohols, amines, thiophenol, acetate, chloride, and fluoride) to these intermediates proceeded smoothly under buffered conditions to give highly functionalized products of general type 5. These reactions were shown to take place with the appropriate selectivities for S(N)2 substitutions in instances where these features were observable, namely, regioselective attack at the less-substituted epoxide carbon and inversion of configuration at the site of substitution. Under acidic conditions dioxaspiropentanes gave mixtures of other types of products, which appear to arise from carbocationic processes.

  DOI：

  10.1021/jo00003a044
• 作为产物：
  描述：

  2-heptyn-1-yl acetate 在 copper(l) iodide 、 水 、 二甲基二环氧乙烷 、 potassium carbonate 、 氯化铵 、 lithium bromide 作用下， 以 丙酮 为溶剂， 反应 3.5h， 生成 2,2-dibutyl-1,4-dioxaspiro<2.2>pentane
  参考文献：
  名称：

  1,4-Dioxaspiro[2.2]pentanes. Synthesis, spectroscopic properties, and reactions with nucleophiles

  摘要：

  A number of simple allenes have been converted cleanly to the corresponding 1,4-dioxaspiro[2.2]pentanes in good yields by oxidation with dimethyldioxirane. Mono- and trisubstituted allenes give the anti diastereomers with good stereoselectivity, whereas 1,3-disubstituted allenes show only a slight preference for the anti,anti isomers, unless steric effects are extreme. Stereochemical assignments are based on steric considerations and a consistent set of NMR characteristics that permit structural attributions. The addition of a range of nucleophiles (water, alcohols, amines, thiophenol, acetate, chloride, and fluoride) to these intermediates proceeded smoothly under buffered conditions to give highly functionalized products of general type 5. These reactions were shown to take place with the appropriate selectivities for S(N)2 substitutions in instances where these features were observable, namely, regioselective attack at the less-substituted epoxide carbon and inversion of configuration at the site of substitution. Under acidic conditions dioxaspiropentanes gave mixtures of other types of products, which appear to arise from carbocationic processes.

  DOI：

  10.1021/jo00003a044

文献信息

• Allene epoxidation. Efficient synthesis and synthetic conversions of 1,4-dioxaspiro[2.2]pentanes
  作者：Jack K. Crandall、David J. Batal

  DOI：10.1021/jo00241a048

  日期：1988.3
• 1,4-Dioxaspiro[2.2]pentanes. Synthesis, spectroscopic properties, and reactions with nucleophiles
  作者：Jack K. Crandall、David J. Batal、David P. Sebesta、Feng Lin

  DOI：10.1021/jo00003a044

  日期：1991.2

  A number of simple allenes have been converted cleanly to the corresponding 1,4-dioxaspiro[2.2]pentanes in good yields by oxidation with dimethyldioxirane. Mono- and trisubstituted allenes give the anti diastereomers with good stereoselectivity, whereas 1,3-disubstituted allenes show only a slight preference for the anti,anti isomers, unless steric effects are extreme. Stereochemical assignments are based on steric considerations and a consistent set of NMR characteristics that permit structural attributions. The addition of a range of nucleophiles (water, alcohols, amines, thiophenol, acetate, chloride, and fluoride) to these intermediates proceeded smoothly under buffered conditions to give highly functionalized products of general type 5. These reactions were shown to take place with the appropriate selectivities for S(N)2 substitutions in instances where these features were observable, namely, regioselective attack at the less-substituted epoxide carbon and inversion of configuration at the site of substitution. Under acidic conditions dioxaspiropentanes gave mixtures of other types of products, which appear to arise from carbocationic processes.