2-hexyl-5,6-dihydro-4H-cyclopenta[b]furan | 1171144-34-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-hexyl-5,6-dihydro-4H-cyclopenta[b]furan
• CAS: 1171144-34-5
• 化学式: C₁₃H₂₀O
• 分子量: 192.301
• InChiKey: WWXCYDQBRKIVIM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  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

文献信息

• Mechanistic Studies and Improvement of Coinage Metal-Catalyzed Transformation of Alkynyloxiranes to Furans: An Alcohol Addition−Cyclization−Elimination Cascade
  作者：Aurélien Blanc、Katharina Tenbrink、Jean-Marc Weibel、Patrick Pale

  DOI：10.1021/jo9008172

  日期：2009.8.7

  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.