3,5-二甲基2H-呋喃并[2,3-c]吡喃-2-酮 | 857054-07-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃吡喃类
• 中文名称: 3,5-二甲基2H-呋喃并[2,3-c]吡喃-2-酮
• 英文名称: 3,5-dimethyl-2H-furo[2,3-c]pyran-2-one
• 英文别名: KAR₃；3,5-dimethylfuro[2,3-c]pyran-2-one
• CAS: 857054-07-0
• 化学式: C₉H₈O₃
• 分子量: 164.161
• InChiKey: LVIAGZUAWKSKRF-UHFFFAOYSA-N

物化性质

• 熔点：
  101-102 °C(Solv: hexane (110-54-3))
• 沸点：
  398.2±25.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于丙酮（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,5-二甲基2H-呋喃并[2,3-c]吡喃-2-酮 在 劳森试剂 、 六甲基二硅氧烷 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以60%的产率得到3,5-dimethyl-2H-furo[2,3-c]pyran-2-thione
  参考文献：
  名称：

  作为潜在神经保护剂的硫卡里金生物等排体的合成

  摘要：

  唯一已知的含硫 karrikin，3-methyl-2 H - thiopyrano[3,4- b ]furan-2-one，最近已被确定为一种极其有效的神经保护性丁烯内酯。在此，我们报告了该化合物的靶向合成以及针对通过氧与硫的生物等排交换衍生自 2 H-呋喃[2,3 - c ]吡喃-2-酮（karrikins）的一类化合物的新合成方案。特别是，我们提出了对 karrikins 生物等排体的合成程序，其中一个或两个硫杂原子掺入核心骨架中，并评估了它们在抑制乙酰胆碱酯酶方面的生物活性。

  DOI：

  10.3762/bjoc.18.57
• 作为产物：
  描述：

  5-hydroxy-2-methyl-thiopyran-4(1H)-one 在 sodium acetate 、 乙酸酐 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 生成 3,5-二甲基2H-呋喃并[2,3-c]吡喃-2-酮
  参考文献：
  名称：

  Preparation of 2H-Furo[2,3-c]pyran-2-one Derivatives and Evaluation of Their Germination-Promoting Activity

  摘要：

  The butenolide, 3-methyl-2H-furo[2,3-c]pyran-2-one (1), has recently been identified as the germination stimulant present in smoke that promotes the germination of seeds from a wide range of plant species. In this paper, we describe the preparation of a number of analogues of 2 and compare their efficacy in promoting seed germination of three highly smoke-responsive plant species, Lactuca sativa L. cv. Grand Rapids (Asteraceae), Emmenanthe penduliflora Benth. (Hydrophyllaceae), and Solanum orbiculatum Poir. (Solanaceae). The results show that the methyl substituent at C-3 in 1 is important for germination-promoting activity while substitution at C-7 reduces activity. In contrast, bioactivity is mostly retained with analogues substituted at C-4 or C-5.

  DOI：

  10.1021/jf0633241

文献信息

• [EN] VINYLOGOUS 4H-PYRONES AND THEIR USE IN PROMOTING PLANT GROWTH<br/>[FR] 4H-PYRONES CONTENANT UN VINYLE ET LEUR UTILISATION POUR FAVORISER LA CROISSANCE DE PLANTES
  申请人：BOTAN GARDENS AND PARKS AUTHOR

  公开号：WO2005061515A1

  公开（公告）日：2005-07-07

  This invention resides in a hitherto unknown class of chemical compounds, 2H-furo[2,3-c]pyran-2-ones including derivatives and analogues thereof. It includes methods for making compounds within said class and includes, without limitation, at least the intermediates employed in the generation of said compounds. The invention also relates to the use of vinylogous 4H-pyrones, including but not limited to the hitherto unknown 2H-furo[2,3-c]pyran-2-ones. In one aspect the invention resides in a method comprising the step of: exposing biological plant material to at least a compound of the invention to promoting bioactivity within said material. In another aspect the invention resides in methods for promoting growth of plant material in, for example, smoke-responsive plant species by exposing said material to a compound of the invention. More specifically, the invention relates to the use of said compounds for promoting seed germination of a plant, for example, a smoke-responsive plant.

  该发明涉及一类迄今未知的化合物，2H-呋喃[2,3-c]吡喃-2-酮及其衍生物和类似物。它包括制备该类化合物的方法，并包括至少用于生成该类化合物的中间体，但不限于此。该发明还涉及使用乙烯基4H-吡喃，包括但不限于迄今未知的2H-呋喃[2,3-c]吡喃-2-酮。在一方面，该发明涉及一种方法，包括步骤：将生物植物材料暴露于发明中的至少一种化合物中，以促进该材料内的生物活性。在另一方面，该发明涉及通过将该材料暴露于发明中的一种化合物中，来促进例如对烟雾敏感的植物物种中的植物材料的生长的方法。更具体地说，该发明涉及使用该类化合物促进植物的种子萌发，例如对烟雾敏感的植物。
• Vinylogous 4-Hpyrones and their use in promoting plant growth
  申请人：Flematti Ray Gavin

  公开号：US20070105721A1

  公开（公告）日：2007-05-10

  A hitherto unknown class of chemical compounds, 2H-furo[2,3-c]pyran-2-ones including derivatives and analogues thereof are disclosed herein. Methods for making compounds within said class are disclosed herein and includes, without limitation, at least the intermediates employed in the generation of said compounds. The invention also relates to the use of vinylogous 4H-pyrones, including but not limited to the hitherto unknown 2H-furo[2,3-c]pyran-2-ones. Disclosed herein are methods comprising the step of exposing biological plant material to at least a compound of the invention to promoting bioactivity within said material. In another aspect in methods for promoting growth of plant material in, for example, smoke-responsive plant species by exposing said material to a compound of the invention are disclosed herein. More specifically, methods comprising the use of these compounds for promoting seed germination of a plant, for example, a smoke-responsive plant, are disclosed herein.

  本文披露了一种迄今未知的化合物类别，包括2H-呋喃[2,3-c]吡喃-2-酮及其衍生物和类似物。本文披露了制备该类化合物的方法，包括但不限于用于生成该类化合物的中间体。本发明还涉及使用缩烯基4H-吡喃，包括但不限于迄今未知的2H-呋喃[2,3-c]吡喃-2-酮。本文披露了一种方法，其中包括将生物植物材料暴露于本发明中的至少一种化合物中，以促进该材料内的生物活性。在另一方面，本文披露了一种促进植物材料生长的方法，例如通过将该材料暴露于本发明中的化合物中来促进对烟雾敏感的植物物种的生长。更具体地说，本文披露了使用这些化合物促进植物种子萌发的方法，例如对于对烟雾敏感的植物。
• COMPOSITIONS AND METHODS FOR TREATING PESTS
  申请人：NOVOZYMES BIOAG A/S

  公开号：US20160270407A1

  公开（公告）日：2016-09-22

  Disclosed herein are pest controlling compositions (i.e., biopesticides) comprising one or more entomopathogenic fungi which. Further disclosed are methods of using such compositions for controlling invasive pests, particularly agriculturally relevant pests.

  本文披露了一种杀虫组合物（即生物杀虫剂），包括一种或多种病原真菌。进一步披露了使用这种组合物控制入侵害虫的方法，特别是农业相关害虫的方法。
• COMPOSITIONS AND METHODS FOR ENHANCING MICROBIAL STABILITY
  申请人：NOVOZYMES BIOAG A/S

  公开号：US20160050915A1

  公开（公告）日：2016-02-25

  Described herein are compositions and methods for increasing the survivability of one or more beneficial microorganisms.

  本文描述了一种增加一种或多种有益微生物生存能力的组合物和方法。
• SEED TREATMENT METHODS AND COMPOSITIONS
  申请人：Novozymes BioAG A/S

  公开号：EP3058826A1

  公开（公告）日：2016-08-24

  Disclosed are methods of enhancing plant growth, comprising treating seed at least one month prior to planting with an effective amount of a plant signal molecule, wherein upon harvesting the plant exhibits at least one of increased plant yield measured in terms of bushels/acre, increased root number, increased root length, increased root mass, increased root volume and increased leaf area, compared to plants harvested from untreated seed, or compared to plants harvested from seed treated with the signal molecule just prior to or within a week or less of planting.

  本发明公开了促进植物生长的方法，包括在播种前至少一个月用有效量的植物信号分子处理种子，其中在收获时，与未处理种子收获的植物相比，或与播种前或播种后一周或更短时间内用信号分子处理的种子收获的植物相比，表现出以蒲式耳/英亩计算的植物产量增加、根数量增加、根长度增加、根质量增加、根体积增加和叶面积增加中的至少一种。