dimethyl 2-[(E)-4-acetyloxybut-2-enyl]-2-methylpropanedioate | 313708-66-6

• 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: dimethyl 2-[(E)-4-acetyloxybut-2-enyl]-2-methylpropanedioate
• CAS: 313708-66-6
• 化学式: C₁₂H₁₈O₆
• 分子量: 258.271
• InChiKey: ZLEVFRLTOCMOEO-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-氧代环戊羧酸乙酯 、 dimethyl 2-[(E)-4-acetyloxybut-2-enyl]-2-methylpropanedioate 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92 mg的产率得到dimethyl 2-[(E)-4-(1-ethoxycarbonyl-2-oxocyclopentyl)but-2-enyl]-2-methylpropanedioate
  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 dimethyl 2-[(E)-4-acetyloxybut-2-enyl]-2-methylpropanedioate
  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

• Allylic geminal diacetates. Unusual carbonyl substitutes via metal catalyzed reactions
  作者：Barry M. Trost、Joseph Vercauteran

  DOI：10.1016/s0040-4039(00)61861-0

  日期：1985.1

  Palladium catalysis facilitates replacement of an acetoxy group of an allylic geminal diacetate by stabilized nucleophiles.

  钯催化促进稳定的亲核试剂代替烯丙基双乙酸双乙酸酯的乙酰氧基。