Acetic acid (3aS,5S,7aR)-2-oxo-2,3,3a,4,5,7a-hexahydro-benzofuran-5-yl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: Acetic acid (3aS,5S,7aR)-2-oxo-2,3,3a,4,5,7a-hexahydro-benzofuran-5-yl ester
• 英文别名: [(3aS,5S,7aR)-2-oxo-3a,4,5,7a-tetrahydro-3H-1-benzofuran-5-yl] acetate
• 化学式: C₁₀H₁₂O₄
• 分子量: 196.203
• InChiKey: RCSWWLWQIDCIDA-YIZRAAEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Acetic acid (3aS,5S,7aR)-2-oxo-2,3,3a,4,5,7a-hexahydro-benzofuran-5-yl ester 在 氢氧化钾 、 水 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以81%的产率得到(3aS,5S,7aR)-5-Hydroxy-3a,4,5,7a-tetrahydro-3H-benzofuran-2-one
  参考文献：
  名称：

  Application of O2-DMSO as Reoxidant in the Pd(II)-Catalyzed 1,4-Oxidation of 5-Substituted 1,3-Cyclohexadienes.

  摘要：

  Palladium-catalyzed oxidation of 5-substituted 1,3-cyclohexadienes carrying a nucleophilic group in the side chain employing O-2-DMSO as the oxidant gave cyclization via 1,4-addition to the 1,3-diene. The nucleophilic groups employed were tosylamido and carboxy. In the reaction Pd-II is most likely reduced to colloidal Pd-0 which is subsequently reoxidized by O-2. The solvent DMSO prevents precipitation of metallic palladium by coordination to the colloidal particles. The stereochemistry of the palladium-catalyzed intramolecular 1,4-oxidation was controlled to some extent by the nature of the external nucleophile. Thus, in the intramolecular 1,4-oxyacyloxylation of 1 (hydroxy as nucleophile in the side chain) it was possible to direct the 1,4-addition towards cis or trans stereochemistry by variation of the external carboxylate nucleophile.

  DOI：

  10.3891/acta.chem.scand.51-0773
• 作为产物：
  描述：

  lithium acetate 、 (2,4-环己二烯基)-乙酸 在 palladium diacetate 、 氧气 、 二甲基亚砜 作用下， 以51%的产率得到Acetic acid (3aS,5S,7aR)-2-oxo-2,3,3a,4,5,7a-hexahydro-benzofuran-5-yl ester
  参考文献：
  名称：

  Application of O2-DMSO as Reoxidant in the Pd(II)-Catalyzed 1,4-Oxidation of 5-Substituted 1,3-Cyclohexadienes.

  摘要：

  Palladium-catalyzed oxidation of 5-substituted 1,3-cyclohexadienes carrying a nucleophilic group in the side chain employing O-2-DMSO as the oxidant gave cyclization via 1,4-addition to the 1,3-diene. The nucleophilic groups employed were tosylamido and carboxy. In the reaction Pd-II is most likely reduced to colloidal Pd-0 which is subsequently reoxidized by O-2. The solvent DMSO prevents precipitation of metallic palladium by coordination to the colloidal particles. The stereochemistry of the palladium-catalyzed intramolecular 1,4-oxidation was controlled to some extent by the nature of the external nucleophile. Thus, in the intramolecular 1,4-oxyacyloxylation of 1 (hydroxy as nucleophile in the side chain) it was possible to direct the 1,4-addition towards cis or trans stereochemistry by variation of the external carboxylate nucleophile.

  DOI：

  10.3891/acta.chem.scand.51-0773

文献信息

• Stereocontrolled lactonization reactions via palladium-catalysis
  作者：Jan-E. Bäckvall、Pher G. Andersson、Jan O. V»gberg

  DOI：10.1016/s0040-4039(01)80345-2

  日期：——

  Dienes 1 were transformed into γ-lactones via a novel stereocontrolled palladium-catalyzed lactonization reaction. The oxylactonization can be directed towards either a cis- or trans-addition across the diene.

  通过新型的立体控制钯催化的内酯化反应，将二烯1转化为γ-内酯。氧化内酯化可以直接穿过二烯进行顺式或反式加成。
• Stereocontrolled lactonization reactions via palladium-catalyzed 1,4-addition to conjugated dienes
  作者：Jan E. Baeckvall、Kenneth L. Granberg、Pher G. Andersson、Roberto Gatti、Adolf Gogoll

  DOI：10.1021/jo00072a029

  日期：1993.9