4-(3-acetylphenyl)pent-4-enoic acid | 1392140-38-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(3-acetylphenyl)pent-4-enoic acid
• CAS: 1392140-38-3
• 化学式: C₁₃H₁₄O₃
• 分子量: 218.252
• InChiKey: XRNJZAZMITYQED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.77
• 重原子数：
  16.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  54.37
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-(3-acetylphenyl)pent-4-enoic acid 在 tetrakis(actonitrile)copper(I) hexafluorophosphate 、 碘苯二乙酸 、 叠氮基三甲基硅烷 、 (S,S)-(-)-2,2'-异亚丙基双(4-叔丁基-2-恶唑啉) 作用下， 以 乙醚 为溶剂， 反应 16.0h， 以52%的产率得到(S)-5-(azidomethyl)-5-(3-acetylphenyl)dihydrofuran-2(3H)-one
  参考文献：
  名称：

  Versatile Enantioselective Synthesis of Functionalized Lactones via Copper-Catalyzed Radical Oxyfunctionalization of Alkenes

  摘要：

  A versatile method for the rapid synthesis of diverse enantiomerically enriched lactones has been developed based on Cu-catalyzed enantioselective radical oxyfunctionalization of alkenes. The scope of this strategy encompasses a series of enantioselective difunctionalization reactions: oxyazidation, oxysulfonylation, oxyarylation, diacyloxylation, and oxyalkylation. These reactions provide straightforward access to a wide range of useful chiral lactone building blocks containing tetrasubstituted stereogenic centers, which are hard to access traditionally.

  DOI：

  10.1021/jacs.5b04821

文献信息

• Enantioselective Functionalization of Radical Intermediates in Redox Catalysis: Copper-Catalyzed Asymmetric Oxytrifluoromethylation of Alkenes
  作者：Rong Zhu、Stephen L. Buchwald

  DOI：10.1002/anie.201307790

  日期：2013.11.25

  Something radical: An efficient enantioselective oxytrifluoromethylation of alkenes has been developed using a copper catalyst system. Mechanistic studies are consistent with a metal‐catalyzed redox radical addition mechanism in which a CO bond is formed by the copper‐mediated enantioselective trapping of a prochiral alkyl radical intermediate derived from the initial trifluoromethyl radical addition

  一些激进的东西：使用铜催化剂系统开发了一种有效的烯烃对映选择性三氟甲基化反应。机理研究与金属催化的氧化还原自由基加成机制一致，其中C - O键是通过铜介导的对映选择性捕获源自初始三氟甲基自由基加成的前手性烷基自由基中间体而形成的。
• Catalytic Enantioselective Halolactonization of Enynes and Alkenes
  作者：Wei Zhang、Na Liu、Casi M. Schienebeck、Kyle Decloux、Suqing Zheng、Jenny B. Werness、Weiping Tang

  DOI：10.1002/chem.201103809

  日期：2012.6.4

  developed for the enantioselective halolactonization of (Z)‐1,3‐enynes and 1,1‐disubstituted alkenes. In the case of 1,3‐enynes, the carboxylate nucleophile and halogen electrophile were added to the conjugated π‐system from the same face. Up to 99 % ee was achieved for the 1,4‐syn‐bromolactonization of conjugated (Z)‐1,3‐enynes. Based on the results from the enyne halolactonization, a second generation

  已开发出新的有机催化剂，用于（Z）-1,3-烯和1,1-二取代烯烃的对映选择性卤代内酯化。在1,3-烯炔的情况下，将羧酸亲核试剂和卤素亲电子试剂从同一面添加到共轭π系统中。共轭（Z）-1,3-烯炔的1,4-顺-溴内酯化可实现高达99％的 ee。基于烯炔卤代内酯化的结果，设计了第二代用于简单烯烃的催化剂。ee高达91％ 观察到1,1-二取代烯烃的氯内酯化。为烯炔和烯烃的对映选择性卤代内酯化而开发的催化剂由拴在脲基上的金鸡纳生物碱骨架组成。