methyl 1-acetyl-cyclopent-3-ene-1-carboxylate | 88326-53-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: methyl 1-acetyl-cyclopent-3-ene-1-carboxylate
• 英文别名: Methyl 1-acetyl-3-cyclopentenecarboxylate；4-acetyl-4-(methoxycarbonyl)cyclopentene；Methyl 1-acetylcyclopent-3-ene-1-carboxylate
• CAS: 88326-53-8
• 化学式: C₉H₁₂O₃
• 分子量: 168.192
• InChiKey: VXFILLHPSWSOGO-UHFFFAOYSA-N

物化性质

• 沸点：
  228.3±40.0 °C(Predicted)
• 密度：
  1.126±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  甲基2-乙酰基-2-丙-2-烯基戊-4-烯酸酯 在 Hoveyda-Grubbs catalyst second generation 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 4.0h， 生成 methyl 1-acetyl-cyclopent-3-ene-1-carboxylate
  参考文献：
  名称：

  Development of a One-Pot Four C–C Bond-Forming Sequence Based on Palladium/Ruthenium Tandem Catalysis

  摘要：

  A one-pot four C-C bond-forming sequence has been developed using two distinct transition metal complexes. The sequence entails a double Pd-catalyzed allylic alkylation followed by a Ru-catalyzed ring-closing metathesis and a Pd-catalyzed Heck coupling. The use of various active methylene nucleophiles was examined with yields up to 76% (93% per C-C bond).

  DOI：

  10.1021/acs.orglett.7b03556

文献信息

• Controllable Cyclization Reactions of 2-(2′,3′-Allenyl)acetylacetates Catalyzed by Gold and Palladium Affording Substituted Cyclopentene and 4,5-Dihydrofuran Derivatives with Distinct Selectivity
  作者：Xuefeng Jiang、Xiaojing Ma、Zilong Zheng、Shengming Ma

  DOI：10.1002/chem.200800793

  日期：2008.9.26

  cyclopentenes and 4,5-dihydrofurans with different substitution patterns were performed starting from the same materials (i.e., 2-(2',3'-allenyl)acetylacetates). Depending on the choice of metal catalyst, the Au-catalyzed reaction afforded C-attack-5-endo cyclization products 2, whereas the Pd-catalyzed one led to the formation of O-attack-5-exo cyclization products 3. The selectivity may be explained by the

  从相同的材料（即2-（2'，3'-烯基）乙酰乙酸酯）开始，高效地合成具有不同取代方式的环戊烯和4,5-二氢呋喃。根据金属催化剂的选择，Au催化的反应提供了C-attack-5-exo环化产物2，而Pd催化的反应导致了O-attack-5-exo环化产物3的形成。可以通过底物和催化剂的空间和电子效应来解释。
• Allylic Alkylation and Ring-Closing Metathesis in Sequence:  A Successful Cohabitation of Pd and Ru
  作者：Claire Kammerer、Guillaume Prestat、Thomas Gaillard、David Madec、Giovanni Poli

  DOI：10.1021/ol702694v

  日期：2008.2.1

  An allylic alkylation/ring-closing metathesis domino catalytic process, wherein a palladium and a ruthenium catalyst are concomitantly present in the reaction mixture from the outset of the reaction, is developed. Evidence for Grubbs' catalysts activity in allylic alkylation is also reported.
• Improved selectivity in the preparation of some 1,1-difunctionalized 3-cyclopentenes. High yield synthesis of 3-cyclopentenecarboxylic acid
  作者：Jean Pierre Depres、Andrew E. Greene

  DOI：10.1021/jo00179a035

  日期：1984.3
• DEPRES, J. -P.;GREENE, A. E., J. ORG. CHEM., 1984, 49, N 5, 928-931
  作者：DEPRES, J. -P.、GREENE, A. E.

  DOI：——

  日期：——
• Development of a One-Pot Four C–C Bond-Forming Sequence Based on Palladium/Ruthenium Tandem Catalysis
  作者：Anne-Doriane Manick、Farouk Berhal、Guillaume Prestat

  DOI：10.1021/acs.orglett.7b03556

  日期：2018.1.5

  A one-pot four C-C bond-forming sequence has been developed using two distinct transition metal complexes. The sequence entails a double Pd-catalyzed allylic alkylation followed by a Ru-catalyzed ring-closing metathesis and a Pd-catalyzed Heck coupling. The use of various active methylene nucleophiles was examined with yields up to 76% (93% per C-C bond).