3a,4-dihydro-1H-cyclopenta[c]furan-5-one | 1067906-28-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: 3a,4-dihydro-1H-cyclopenta[c]furan-5-one
• 英文别名: (6aS)-1,3,6,6a-tetrahydrocyclopenta[c]furan-5-one
• CAS: 1067906-28-8
• 化学式: C₇H₈O₂
• 分子量: 124.139
• InChiKey: ZKZIZFZTGXIFDI-ZCFIWIBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  allyl propargyl ether 、 一氧化碳 在 di(rhodium)tetracarbonyl dichloride silver trifluoromethanesulfonate 作用下， 以 四氢呋喃 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 0.5h， 以18%的产率得到3a,4-dihydro-1H-cyclopenta[c]furan-5-one
  参考文献：
  名称：

  Asymmetric Pauson−Khand-type Reaction Mediated by Rh(I) Catalyst at Ambient Temperature

  摘要：

  An efficient asymmetric PKR mediated by Rh(I) catalyst at ambient temperature was developed. The reaction utilizing a Rh(I) catalyst bearing a (R)-3,5-diMeC(4)H(4)-BINAP ligand at 18-20 degrees C under a reduced partial pressure of CO (0.1 atm) provided PKR products in high chemical yield as well as high enantioselectivity.

  DOI：

  10.1021/jo801236c

文献信息

• Asymmetric Pauson−Khand-type Reaction Mediated by Rh(I) Catalyst at Ambient Temperature
  作者：Dong Eun Kim、In Su Kim、Virginie Ratovelomanana-Vidal、Jean-Pierre Genêt、Nakcheol Jeong

  DOI：10.1021/jo801236c

  日期：2008.10.17

  An efficient asymmetric PKR mediated by Rh(I) catalyst at ambient temperature was developed. The reaction utilizing a Rh(I) catalyst bearing a (R)-3,5-diMeC(4)H(4)-BINAP ligand at 18-20 degrees C under a reduced partial pressure of CO (0.1 atm) provided PKR products in high chemical yield as well as high enantioselectivity.
• 2,2′‐Bis[bis(3,5‐di‐<i>tert</i>‐butyl‐4‐methoxyphenyl)phosphino]‐6,6′‐dimethoxy‐1,1′‐biphenyl in Intramolecular Rhodium(I)‐Catalyzed Asymmetric Pauson–Khand‐Type Reactions
  作者：Dong Eun Kim、Virginie Ratovelomanana‐Vidal、Nakcheol Jeong

  DOI：10.1002/adsc.201000221

  日期：2010.10.9

  AbstractA cationic rhodium(I)/2,2′‐bis[bis(3,5‐di‐tert‐butyl‐4‐methoxyphenyl)phosphino]‐6,6′‐dimethoxy‐1,1′‐biphenyl (DTBM‐MeO‐BIPHEP) catalyst was highly efficient for the asymmetric catalytic Pauson–Khand reaction, especially for those substrates containing aryl group‐substituted alkynes. The formation of the products that were derived from a β‐hydride eliminated intermediate 5 was completely suppressed over a wide range of substrates. This reaction was a serious process competing reaction with the migratory CO insertion that led to the Pauson–Khand reaction product and often substantially ruined the chemical yield of the Pauson–Khand reaction. The advantages of this system were clearly demonstrated for previously troublesome substrates, N‐tosyl‐ (1b) and malonate‐tethered 1,6‐enynes (1c), that exhibited a higher enantioselectivity without a loss in the chemical yields. The obvious beneficial effects were attributed to the synergic effect of various factors, such as the electron density of the phosphorus of the ligand, the dihedral angles of the atropisomeric ligand, and the substitution on the phosphine aryl rings which play a crucial role in the stereochemical outcome of Rh‐catalyzed Pauson–Khand reaction.