(R,E)-2-methyl-4-(4-methylene-5-oxotetrahydrofuran-3-yl)but-2-enal | 1338472-00-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (R,E)-2-methyl-4-(4-methylene-5-oxotetrahydrofuran-3-yl)but-2-enal
• 英文别名: (E)-2-methyl-4-[(3R)-4-methylidene-5-oxooxolan-3-yl]but-2-enal
• CAS: 1338472-00-6
• 化学式: C₁₀H₁₂O₃
• 分子量: 180.203
• InChiKey: ARQXVBHZLIMZFL-HMVTZJNGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R,E)-2-methyl-4-(4-methylene-5-oxotetrahydrofuran-3-yl)but-2-enal 在 sodium tetrahydroborate 、 cerium(III) chloride heptahydrate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以87%的产率得到(R,E)-4-(4-hydroxy-3-methylbut-2-en-1-yl)-3-methylenedihydrofuran-2(3H)-one
  参考文献：
  名称：

  Catalytic Asymmetric Synthesis of (+)-Anthecotulide Using Enyne and Meyer–Schuster Rearrangements

  摘要：

  The bioactive sesquiterpene lactone (+)-anthecularin (1) is synthesized for the first time, in a six-step sequence devoid of protecting groups. The key transformations are a novel Rh(I)-catalyzed asymmetric enyne rearrangement of a terminal alkynyl ester (4), to form the alpha-methylene-gamma-butyrolactone core, and a final-step mild Au(I)-catalyzed Meyer-Schuster rearrangement

  DOI：

  10.1021/ol202425e
• 作为产物：
  描述：

  cis-4-hydroxybut-2-en-1-ylprop-2-ynoate 在 silver hexafluoroantimonate 、 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl 作用下， 以 1,2-二氯乙烷 、 丙酮 为溶剂， 反应 87.0h， 生成 (R,E)-2-methyl-4-(4-methylene-5-oxotetrahydrofuran-3-yl)but-2-enal
  参考文献：
  名称：

  Catalytic Asymmetric Synthesis of (+)-Anthecotulide Using Enyne and Meyer–Schuster Rearrangements

  摘要：

  The bioactive sesquiterpene lactone (+)-anthecularin (1) is synthesized for the first time, in a six-step sequence devoid of protecting groups. The key transformations are a novel Rh(I)-catalyzed asymmetric enyne rearrangement of a terminal alkynyl ester (4), to form the alpha-methylene-gamma-butyrolactone core, and a final-step mild Au(I)-catalyzed Meyer-Schuster rearrangement

  DOI：

  10.1021/ol202425e

文献信息

• Catalytic Asymmetric Synthesis of (+)-Anthecotulide Using Enyne and Meyer–Schuster Rearrangements
  作者：David M. Hodgson、Eric P. A. Talbot、Barry P. Clark

  DOI：10.1021/ol202425e

  日期：2011.11.4

  The bioactive sesquiterpene lactone (+)-anthecularin (1) is synthesized for the first time, in a six-step sequence devoid of protecting groups. The key transformations are a novel Rh(I)-catalyzed asymmetric enyne rearrangement of a terminal alkynyl ester (4), to form the alpha-methylene-gamma-butyrolactone core, and a final-step mild Au(I)-catalyzed Meyer-Schuster rearrangement