ethyl 1-(4-acetoxybut-2-enyl)-2-oxocyclopentanecarboxylate | 313708-67-7

• 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: ethyl 1-(4-acetoxybut-2-enyl)-2-oxocyclopentanecarboxylate
• 英文别名: ethyl 1-[(E)-4-acetyloxybut-2-enyl]-2-oxocyclopentane-1-carboxylate
• CAS: 313708-67-7
• 化学式: C₁₄H₂₀O₅
• 分子量: 268.31
• InChiKey: NNPUVBDSPQRGRO-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,3-环己二酮 、 ethyl 1-(4-acetoxybut-2-enyl)-2-oxocyclopentanecarboxylate 在 sodium hydride 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以58%的产率得到ethyl 1-[(E)-4-[1-[(E)-4-(1-ethoxycarbonyl-2-oxocyclopentyl)but-2-enyl]-2,6-dioxocyclohexyl]but-2-enyl]-2-oxocyclopentane-1-carboxylate
  参考文献：
  名称：

  Synthesis of Stereodefined Polysubstituted Olefins. 1. Sequential Intermolecular Reactions Involving Selective, Stepwise Insertion of Pd(0) into Allylic and Vinylic Halide Bonds. The Stereoselective Synthesis of Disubstituted Olefins¹

  摘要：

  Palladium-catalyzed allylic substitution and cross-coupling reactions have been combined into a sequential procedure to provide a range of disubstituted olefin products starting from two-, three-, and four-carbon common olefin templates. Diverse application of this template strategy is demonstrated in a variety of model studies and in a parallel synthesis (combinatorial) approach to prepare an allylic amine molecular library. An approach toward the preparation of astaxanthin beta -D-diglucoside, an interesting antioxidant whose total synthesis has yet to be reported, using the olefin-template approach is also discussed.

  DOI：

  10.1021/jo001045l
• 作为产物：
  描述：

  丁-2-烯-1,4-二醇乙酸酯 在 N-氯代丁二酰亚胺 、 二甲基硫 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.25h， 生成 ethyl 1-(4-acetoxybut-2-enyl)-2-oxocyclopentanecarboxylate
  参考文献：
  名称：

  Synthesis of Stereodefined Polysubstituted Olefins. 1. Sequential Intermolecular Reactions Involving Selective, Stepwise Insertion of Pd(0) into Allylic and Vinylic Halide Bonds. The Stereoselective Synthesis of Disubstituted Olefins¹

  摘要：

  Palladium-catalyzed allylic substitution and cross-coupling reactions have been combined into a sequential procedure to provide a range of disubstituted olefin products starting from two-, three-, and four-carbon common olefin templates. Diverse application of this template strategy is demonstrated in a variety of model studies and in a parallel synthesis (combinatorial) approach to prepare an allylic amine molecular library. An approach toward the preparation of astaxanthin beta -D-diglucoside, an interesting antioxidant whose total synthesis has yet to be reported, using the olefin-template approach is also discussed.

  DOI：

  10.1021/jo001045l

文献信息

• Reluctant Cross-Metathesis Reactions: The Highly Beneficial Effect of Microwave Irradiation
  作者：Yoann Coquerel、Jean Rodriguez、Antoine Michaut、Thomas Boddaert

  DOI：10.1055/s-2007-983825

  日期：2007.9

  The beneficial effect of microwave irradiation versus classical thermal conditions is demonstrated through a series of comparative cross-metathesis reactions.

  微波辐射相对于传统热条件的有益效果通过一系列比较的交叉转烯反应得以证明。