3-[(2,5-dihydro-3-methyl-2-oxo-5-furanyl)oxo]methylene-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-2-one | 118016-86-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 3-[(2,5-dihydro-3-methyl-2-oxo-5-furanyl)oxo]methylene-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-2-one
• 英文别名: (3aR,6aR,5'R)3-<<(2,5-dihydro-3-methyl-2-oxo-5-furanyl)oxo>methylene>-3,3a,6,6a-tetrahydro-2H-cyclopentafuran-2-on；3-(4-methyl-5-oxo-2,5-dihydro-furan-2(R)-yloxymethylene)-3,3a(R),6,6a(R)-tetrahydrocyclopentafuran-2-one；(3E,3aR,6aR)-3-[[(2R)-4-methyl-5-oxo-2H-furan-2-yl]oxymethylidene]-6,6a-dihydro-3aH-cyclopenta[b]furan-2-one
• CAS: 118016-86-7
• 化学式: C₁₃H₁₂O₅
• 分子量: 248.235
• InChiKey: BAQQOIFUXUUHKH-GEGCJXFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2(S)-methyl-5(R)-(2-oxo-3a(R),6a(R)-dihydro-6H-cyclopentafuran-3-ylidenemeth-oxy)-4-oxa-exo tricyclo<5.2.1.0^2.6>dec-8-en-3-one 以 邻二氯苯 为溶剂， 反应 15.0h， 以64%的产率得到3-[(2,5-dihydro-3-methyl-2-oxo-5-furanyl)oxo]methylene-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-2-one
  参考文献：
  名称：

  Asymmetric synthesis of a D-ring synthon for strigol analogues and its application to the synthesis of all four stereoisomers of germination stimulant GR7

  摘要：

  DOI：

  10.1016/0040-4020(95)98701-i

文献信息

• An Efficient Enantioselective Synthesis of Strigolactones with a Palladium-Catalyzed Asymmetric Coupling as the Key Step
  作者：Anat Reizelman、Binne Zwanenburg

  DOI：10.1002/1099-0690(200203)2002:5<810::aid-ejoc810>3.0.co;2-u

  日期：2002.3

  An efficient enantioselective methodology for the preparation of the strigolactones GR7, GR24 and Nijmegen-1 based on palladium-catalyzed asymmetric coupling has been developed, The products are obtained in good yield and high optical purity. This Methodology is an attractive alternative for installing the stereochemisry at C2' of the D-ring. ((C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).
• Asymmetric synthesis of a D-ring synthon for strigol analogues and its application to the synthesis of all four stereoisomers of germination stimulant GR7
  作者：Jan Willem J.F. Thuring、Gerard H.L. Nefkens、Robert Schaafstra、Binne Zwanenburg

  DOI：10.1016/0040-4020(95)98701-i

  日期：1995.4