2,2-dibutyl-3-oxacyclobutanone | 131864-34-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 2,2-dibutyl-3-oxacyclobutanone
• 英文别名: 2,2-dibutyloxetan-3-one
• CAS: 131864-34-1
• 化学式: C₁₁H₂₀O₂
• 分子量: 184.279
• InChiKey: LVNUIYFXCUYQJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-butyl-1,2-heptadiene 在 二甲基二环氧乙烷 作用下， 以 氯仿 、 甲苯 为溶剂， 以70%的产率得到2,2-dibutyl-3-oxacyclobutanone
  参考文献：
  名称：

  通过螺旋二环氧化合物从丙二烯中制得Oxetan-3-ones

  摘要：

  据报道，有两种简洁的方法可以从丙二烯生成氧杂环丁烷-3-酮。第一种方法采用烯丙基环氧化，通过卤化物亲核试剂打开螺二环氧化物，然后在分子内用醇盐置换卤化物。第二种方法涉及丙二烯环氧化，然后将相应的螺二环氧化物热重排为oxetan-3-one。两种方法是互补的和立体化学的。还介绍了热重排的计算分析。

  DOI：

  10.1021/ol400749e

文献信息

• 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.
• CRANDALL, JACK K.;BATAL, DAVID J.;SEBESTA, DAVID P.;LIN, FENG, J. ORG. CHEM., 56,(1991) N, C. 1153-1166
  作者：CRANDALL, JACK K.、BATAL, DAVID J.、SEBESTA, DAVID P.、LIN, FENG

  DOI：——

  日期：——