methyl 2-oxo-5,5-diphenyltetrahydrofuran-3-carboxylate | 36262-59-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 2-oxo-5,5-diphenyltetrahydrofuran-3-carboxylate
• 英文别名: 2-oxo-5,5-diphenyl-tetrahydro-furan-3-carboxylic acid methyl ester；Methyl 2-oxo-5,5-diphenyloxolane-3-carboxylate
• CAS: 36262-59-6
• 化学式: C₁₈H₁₆O₄
• 分子量: 296.323
• InChiKey: VRZXLXFCGDJZIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,1-二苯乙烯 、 溴丙二酸二甲酯 在 lithium tetrafluoroborate 、 fac-Ir(ppy)₃ 作用下， 以 水 、 乙腈 为溶剂， 反应 24.0h， 以95%的产率得到methyl 2-oxo-5,5-diphenyltetrahydrofuran-3-carboxylate
  参考文献：
  名称：

  A Novel Intermolecular Synthesis of γ-Lactones via Visible-Light Photoredox Catalysis

  摘要：

  Direct gamma-lactone formation via visible-light photoredox catalysis has been achieved efficiently including hydroxylalkylation of aromatic alkenes and transesterification. The present photocatalytic protocol has good regioselectivity and substrate compatibility, affording a novel way to intermolecular gamma-lactone synthesis by the reaction of styrenes with alpha-bromo esters in the absence of any external oxidants.

  DOI：

  10.1021/ol402954t

文献信息

• Succinimide-Promoted Malonylamination of Alkenes with Amines and Iodonium Ylides via Trapping of Transient Aminium Radical Cations
  作者：Liang Zhang、Xiangjin Kong、Shuya Liu、Zhiguo Zhao、Qun Yu、Wei Wang、Yao Wang

  DOI：10.1021/acs.orglett.9b00983

  日期：2019.4.19

  A conceptually distinct strategy enabling malonylamination of alkenes with abundant amines and iodonium ylides without assistance of any transition metal was developed. Succinimide was identified as a proton shuttle that can not only largely accelerate the process of trapping highly unstable radical ion pairs with alkenes but also significantly improve the chemical yields.

  开发了一种在概念上独特的策略，该策略无需大量过渡金属即可使烯烃与丰富的胺和碘鎓碘化物进行丙二醛层压。琥珀酰亚胺被认为是质子穿梭体，它不仅可以大大加速用烯烃捕获高度不稳定的自由基离子对的过程，而且还可以显着提高化学收率。