2-methyl-4-(2-oxo-2,3,3a,8b-tetrahydro-4H-indeno[1,2-b]furan-3-ylidenemethoxy)but-2-en-4-olide | 188062-51-3

• 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: 2-methyl-4-(2-oxo-2,3,3a,8b-tetrahydro-4H-indeno[1,2-b]furan-3-ylidenemethoxy)but-2-en-4-olide
• 英文别名: epi-(-)-Strigolactone GR24；(3E,3aS,8bR)-3-[[(2R)-4-methyl-5-oxo-2H-furan-2-yl]oxymethylidene]-4,8b-dihydro-3aH-indeno[1,2-b]furan-2-one
• CAS: 188062-51-3
• 化学式: C₁₇H₁₄O₅
• 分子量: 298.295
• InChiKey: XHSDUVBUZOUAOQ-VEEPAONSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  3-(6(S)-methyl-5-oxo-4-oxatricyclo[5.2.1.0^2,6]dec-8-en-3(R)-yloxymethylene)-3,3a(S),4,8b(R)-tetrahydroindeno[1,2-b]furan-2-one 以 邻二氯苯 为溶剂， 反应 14.0h， 以58%的产率得到2-methyl-4-(2-oxo-2,3,3a,8b-tetrahydro-4H-indeno[1,2-b]furan-3-ylidenemethoxy)but-2-en-4-olide
  参考文献：
  名称：

  Asymmetric Synthesis of All Stereoisomers of the Strigol Analogue GR24. Dependence of Absolute Configuration on Stimulatory Activity of Striga hermonthica and Orobanche crenata Seed Germination

  摘要：

  All four optically pure stereoisomers of the strigol analogue GR24 were prepared via two different routes. In the first approach enantiopure ABC-fragments 4 were used as the chiral source, whereas in the alternative route both antipodes of the latent D-ring 6 were employed. Bioassays revealed significant differences in activity between the four stereoisomers in the stimulation of germination of the parasitic weeds Striga hermonthica and Orobanche crenata.

  DOI：

  10.1021/jf960466u

文献信息

• SUBSTITUTED 5-(BICYCLO[4.1.0]HEPT-3-EN-2-YL)PENTA-2,4-DIENES AND 5-(BICYCLO[4.1.0]HEPT-3-EN-2-YL)PENT-2-ENE-4-INES AS ACTIVE AGENTS AGAINST ABIOTIC STRESSES IN PLANTS
  申请人：Frackenpohl Jens

  公开号：US20140051577A1

  公开（公告）日：2014-02-20

  The invention relates to substituted 5-(bicyclo[4.1.0]hept-3-en-2-yl)penta-2,4-dienes and 5-(bicyclo[4.1.0]hept-3-en-2-yl)pent-2-ene-4-ines of the formula (I) and salts thereof, where the radicals R1, R2, R3, R4, R5, [X—Y] and Q are each as defined in the description, to processes for preparation thereof and to the use thereof for enhancing stress tolerance in plants with respect to abiotic stress, and/or for increasing plant yield.

  该发明涉及代换的5-(bicyclo[4.1.0]庚-3-烯-2-基)戊-2,4-二烯和5-(bicyclo[4.1.0]庚-3-烯-2-基)戊-2-烯-4-炔的化合物及其盐，其中基团R1、R2、R3、R4、R5、[X—Y]和Q的定义如描述中所示，以及其制备方法和用途，用于增强植物对非生物胁迫的抗压能力，和/或增加植物产量。
• Substituted Fused Pyrimidinones and Dihydropyrimidinones
  申请人：FRACKENPOHL Jens

  公开号：US20120157306A1

  公开（公告）日：2012-06-21

  The use of substituted fused pyrimidinones and dihydropyrimidinones of the formula (I) or salts thereof where the radicals of the formula (I) are each as defined in the description, for enhancing stress tolerance in plants to abiotic stress, and for invigorating plant growth and/or for increasing plant yield.

  使用公式（I）中定义的基团的取代融合嘧啶酮和二氢嘧啶酮或其盐，用于增强植物对非生物胁迫的耐受性，激发植物生长和/或增加植物产量。
• 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).
• GR 24 Enantiomers:  Synthesis, NMR Spectroscopy, X-ray Crystallography, and Separation by Chiral Electrokinetic Capillary Chromatography
  作者：Joseph K. Rugutt、H. Hyacinthe Yarabe、Shahab A. Shamsi、Damon R. Billodeaux、Frank R. Fronczek、Isiah M. Warner

  DOI：10.1021/ac991438o

  日期：2000.8.1

  Chiral discrimination of enantiomers of 2-methyl-4-(2-oxo-2,3,3a,8b-tetrahydro-4H-indeno[1,2b]furan-3-ylidenemethoxy)but-2-en-4-olide (commonly referred to as GR 24) by three polymeric chiral surfactants (PCS) is studied by use of chiral polymeric surfactant capillary electrophoresis (CPSCE). The CPSCE results indicate that the optical configurations of valine residues on the PCS backbone affect chiral resolution and elution order of GR24 stereoisomers. The l- and d-forms of poly(sodium N-undecanoyl valinate) provide baseline separation of all four enantiomers while the dl-form separates diastereomers of GR 24 (1). A model is presented rationalizing the migration behavior and chiral resolution of 1 in CPSCE. The actual configuration of the stereogenic centers of GR 24 and 3-[(2,5-dihydro-3-methyl-2-oxo-5-furanyl)oxo]methylene-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-2-one (GR 7) is established by a concerted application of high-resolution nuclear magnetic resonance spectroscopy and X-ray crystallography.
• [EN] ROOT PARASITIC PLANT GERMINATION MODIFIER AND METHOD FOR CONTROL OF ROOT PARASITIC PLANT USING SAME<br/>[FR] MODIFICATEUR DE LA GERMINATION DES PLANTES À RACINE-SUÇOIR ET PROCÉDÉ DE LUTTE CONTRE LES PLANTES À RACINE-SUÇOIR L'UTILISANT
  申请人：NAT UNIV CORP UNIV KOBE

  公开号：WO2012157404A1

  公开（公告）日：2012-11-22

  発明は、新規な根寄生植物発芽調節剤を提供する。また、当該根寄生植物発芽調節剤を含む根寄生植物防除剤を提供する。さらには、当該根寄生植物防除剤を用いて根寄生植物を防除する方法を提供する。下記の一般式(I)で表され、かつ特定の立体構造を有する化合物による。（式(I)中、R1とR2は、結合して五～六員環のいずれかの環を形成していてもよく、前記環はベンゼン環、又は非置換若しくはメチル基で置換されていてもよいシクロアルケニル環であり、あるいはそれぞれ独立して水素原子、メチル基、エチル基、又はC3～C6の直鎖状若しくは分枝状の低級アルキル基を表し、R3は、水素原子、水酸基、アセトキシ基より選択され、R4は、水素原子である。）