6-vinyl-7-oxa-bicyclo[4.2.0]octane | 33879-65-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环丁烷
• 英文名称: 6-vinyl-7-oxa-bicyclo[4.2.0]octane
• 英文别名: 6-Ethenyl-7-oxabicyclo[4.2.0]octane
• CAS: 33879-65-1
• 化学式: C₉H₁₄O
• 分子量: 138.21
• InChiKey: IMVOVMKEHIVBPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-vinyl-7-oxa-bicyclo[4.2.0]octane 、 对甲氧基苯异氰酸酯 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 1,3-双(二苯基膦)丙烷 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以55%的产率得到
  参考文献：
  名称：

  Synthesis of 1,3-Oxazine Derivatives by Palladium-Catalyzed Cycloaddition of Vinyloxetanes with Heterocumulenes. Completely Stereoselective Synthesis of Bicyclic 1,3-Oxazines

  摘要：

  1,3-Oxazines were prepared by palladium-phosphine-catalyzed cycloaddition reactions of vinyloxetanes with heterocumulenes. 4-Vinyl-1,3-oxazin-2-imines were obtained in fine yields by the reaction of 2-vinyloxetanes with carbodiimides in THF at rt for 12 h using 1.5 mol % Pd-2(dba)(3). CHCl3 and 3 mol % bidentate phosphine ligands (dppe or dppp). When isocyanates were utilized in the reaction, moderate to good yields of 4-vinyl-1,3-oxazin-2-ones were achieved within 1-2 h at rt. Palladium-catalyzed cycloaddition of fused-bicyclic vinyloxetanes with heterocumulenes proceeds in a highly stereoselective fashion affording only the cis-3-aza-1-oxo-9-vinyl[4.4.0]decane derivatives in 43-98% yield.

  DOI：

  10.1021/jo990430b

文献信息

• Highly stereoselective synthesis of di- and trisubstituted homoallylic alcohols via palladium(O)-catalyzed nucleophilic opening of vinylic oxetanes
  作者：Richard C. Larock、Sandra K. Stolz-Dunn

  DOI：10.1016/s0040-4039(00)99420-6

  日期：1989.1

  Vinylic oxetanes react in an SN2′ manner with a variety of potential nucleophiles in the presence of catalytic amounts of Pd(PPh3)4 to afford the corresponding highly functionalized, di- and trisubstituted homoallylic alcohols with high stereoselectivity.

  在催化量的Pd（PPh 3）4存在下，乙烯基氧杂环丁烷以S N 2'的方式与多种潜在的亲核试剂反应，从而提供具有高立体选择性的相应的高度官能化的二取代和三取代的均烯丙基醇。
• LAROCK, RICHARD C.;STOLZ-DUNN, SANDRA K., TETRAHEDRON LETT., 30,(1989) N7, C. 3487-3490
  作者：LAROCK, RICHARD C.、STOLZ-DUNN, SANDRA K.

  DOI：——

  日期：——
• Synthesis of 1,3-Oxazine Derivatives by Palladium-Catalyzed Cycloaddition of Vinyloxetanes with Heterocumulenes. Completely Stereoselective Synthesis of Bicyclic 1,3-Oxazines
  作者：Chitchamai Larksarp、Howard Alper

  DOI：10.1021/jo990430b

  日期：1999.5.1

  1,3-Oxazines were prepared by palladium-phosphine-catalyzed cycloaddition reactions of vinyloxetanes with heterocumulenes. 4-Vinyl-1,3-oxazin-2-imines were obtained in fine yields by the reaction of 2-vinyloxetanes with carbodiimides in THF at rt for 12 h using 1.5 mol % Pd-2(dba)(3). CHCl3 and 3 mol % bidentate phosphine ligands (dppe or dppp). When isocyanates were utilized in the reaction, moderate to good yields of 4-vinyl-1,3-oxazin-2-ones were achieved within 1-2 h at rt. Palladium-catalyzed cycloaddition of fused-bicyclic vinyloxetanes with heterocumulenes proceeds in a highly stereoselective fashion affording only the cis-3-aza-1-oxo-9-vinyl[4.4.0]decane derivatives in 43-98% yield.