tricyclo<3.2.1.0^2,4>oct-2(4)-ene | 143668-20-6

• 分子结构分类: 有机化合物 - 碳氢化合物 - 多环烃
• 英文名称: tricyclo<3.2.1.0^2,4>oct-2(4)-ene
• 英文别名: Tricyclo[3.2.1.02,4]oct-2(4)-ene；tricyclo[3.2.1.02,4]oct-2(4)-ene
• CAS: 143668-20-6
• 化学式: C₈H₁₀
• 分子量: 106.167
• InChiKey: RBZNDBWSBXSIBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  (1S,2S,4R,5R)-2,4-dibromotricyclo[3.2.1.02,4]octane 在 1,3-二苯基异苯并呋喃 、 叔丁基锂 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 以0.40 g的产率得到tricyclo<3.2.1.0^2,4>oct-2(4)-ene
  参考文献：
  名称：

  Synthesis and chemistry of some tricyclic cyclopropenes. 3. Tricyclo[3.2.1.02,4]oct-2(4)-ene

  摘要：

  The title compound cyclopropene 2 has been synthesized in situ from dibromide 8 and diiodide 9 via dehalogenation of tert-butyllithium in THF at -78-degrees-C. The dihalides were formed in six steps starting with cyclopentadiene and (chloromethyl)maleic anhydride. In the presence of diphenylisobenzofuran (DPIBF) 2 forms a Diels-Alder adduct, most probably 10. Cyclopropene 2 and a previously synthesized cyclopropene 1 were decomposed under these same conditions, only without DPIBF present, to give complex mixtures of products, some of which were characterized as tert-butyl adducts and dimers via the ene reaction of the cyclopropenes.

  DOI：

  10.1021/jo00048a032

文献信息

• Synthesis and chemistry of some tricyclic cyclopropenes. 3. Tricyclo[3.2.1.02,4]oct-2(4)-ene
  作者：Philip J. Chenier、Michael J. Bauer、Christina L. Hodge

  DOI：10.1021/jo00048a032

  日期：1992.10

  The title compound cyclopropene 2 has been synthesized in situ from dibromide 8 and diiodide 9 via dehalogenation of tert-butyllithium in THF at -78-degrees-C. The dihalides were formed in six steps starting with cyclopentadiene and (chloromethyl)maleic anhydride. In the presence of diphenylisobenzofuran (DPIBF) 2 forms a Diels-Alder adduct, most probably 10. Cyclopropene 2 and a previously synthesized cyclopropene 1 were decomposed under these same conditions, only without DPIBF present, to give complex mixtures of products, some of which were characterized as tert-butyl adducts and dimers via the ene reaction of the cyclopropenes.