1-辛-1-炔基-6-氧杂二环[3.1.0]己烷 | 58149-20-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 中文名称: 1-辛-1-炔基-6-氧杂二环[3.1.0]己烷
• 英文名称: 1-(1-octynyl)-6-oxabicyclo<3.1.0>hexane
• 英文别名: 1-(oct-1-ynyl)-6-oxa-bicyclo[3.1.0]hexane；1,2-epoxy-1-(1-octynyl)-1-cyclopentene；1,2-epoxy-1-oct-1-ynyl-cyclopentane；1-(Oct-1-YN-1-YL)-6-oxabicyclo[3.1.0]hexane；1-oct-1-ynyl-6-oxabicyclo[3.1.0]hexane
• CAS: 58149-20-5
• 化学式: C₁₃H₂₀O
• 分子量: 192.301
• InChiKey: FZIASBCNOSFVIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-辛-1-炔基-6-氧杂二环[3.1.0]己烷 在 甲醇 、 三苯基膦氯金 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 以20%的产率得到2-hexyl-5,6-dihydro-4H-cyclopenta[b]furan
  参考文献：
  名称：

  Mechanistic Studies and Improvement of Coinage Metal-Catalyzed Transformation of Alkynyloxiranes to Furans: An Alcohol Addition−Cyclization−Elimination Cascade

  摘要：

  In the presence of alcohol Ag or Au salts or complexes catalyze the conversion of alkynyloxiranes to substituted furans. Both-catalysts are effective, and a large furan diversity can be obtained in high yield with one or the other catalyst. Mechanistic studies revealed that a cascade pathway and not the sometimes reported direct intra molecular nucleophilic addition of oxirane oxygen atom to intermediate acetylene-metal pi-complex occurs. Under the defined conditions, the intermediate formation of epoxide opening products has been identified. Depending on the catalyst, one or both of the latter cyclized to dihydrofurans, and further elimination of the alcohol led to the corresponding furans. These results highlight the duality between oxophilicity and alkynophilicity of Ag or Au salts.

  DOI：

  10.1021/jo9008172
• 作为产物：
  描述：

  1-(1-辛炔基)-1-环戊烯 在 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 1-辛-1-炔基-6-氧杂二环[3.1.0]己烷
  参考文献：
  名称：

  Silver(I)-Catalyzed Cascade: Direct Access to Furans from Alkynyloxiranes

  摘要：

  Functionalized furans are conveniently formed by a new silver(I)-catalyzed reaction of alk-1-ynyl oxiranes in the presence of p-toluenesulfonic acid and methanol. Evidence supported a cascade mechanism.

  DOI：

  10.1021/jo900483m

文献信息

• Denisov, V. R.; Lupaeva, M. L.; Alekseeva, E. M., Journal of Organic Chemistry USSR (English Translation), 1990, vol. 26, # 2.1, p. 251 - 256
  作者：Denisov, V. R.、Lupaeva, M. L.、Alekseeva, E. M.、Schaumann, E.

  DOI：——

  日期：——
• Untersuchungen �ber die Bildung von 2-Acylcyclopentanonen aus 1-(1-�thynyl)-cyclopentenen und Perameisens�ure
  作者：Karl Eichinger

  DOI：10.1007/bf01153928

  日期：——
• DENISOV, V. R.;LUPAEVA, M. L.;ALEKSEEVA, EH. M.;SHAUMANN, EH., ZH. ORGAN. XIMII, 26,(1990) N, S. 299-305
  作者：DENISOV, V. R.、LUPAEVA, M. L.、ALEKSEEVA, EH. M.、SHAUMANN, EH.

  DOI：——

  日期：——
• Denisov, V. R.; Khimich, G. N.; Shevchenko, Z. A., Russian Journal of Organic Chemistry, 1986, vol. 22, # 12, p. 2273 - 2278
  作者：Denisov, V. R.、Khimich, G. N.、Shevchenko, Z. A.、Favorskaya, I. A.

  DOI：——

  日期：——
• Silver(I)-Catalyzed Cascade: Direct Access to Furans from Alkynyloxiranes
  作者：Aurélien Blanc、Katharina Tenbrink、Jean-Marc Weibel、Patrick Pale

  DOI：10.1021/jo900483m

  日期：2009.6.5

  Functionalized furans are conveniently formed by a new silver(I)-catalyzed reaction of alk-1-ynyl oxiranes in the presence of p-toluenesulfonic acid and methanol. Evidence supported a cascade mechanism.