4-methyl-2-(4-methylphenoxy)-2H-furan-5-one | 1332863-98-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-methyl-2-(4-methylphenoxy)-2H-furan-5-one
• CAS: 1332863-98-5
• 化学式: C₁₂H₁₂O₃
• 分子量: 204.225
• InChiKey: BEXCDTZXWJIRSI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-bromo-4-methyl-2H-furan-5-one 、 对甲酚 在 四丁基溴化铵 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 8.0h， 以29%的产率得到4-methyl-2-(4-methylphenoxy)-2H-furan-5-one
  参考文献：
  名称：

  New branching inhibitors and their potential as strigolactone mimics in rice

  摘要：

  Strigolactones (SLs) are rhizosphere communication chemicals. Recent studies of highly branched mutants revealed that SL or its metabolites work as a phytohormone to inhibit shoot branching. When SLs are exogenously applied to the rice d10-1 mutant that has a highly branched phenotype caused by a defect in the SL biosynthesis gene (CCD8), they inhibit tiller bud outgrowth (branching in rice) of the mutant. We focused our attention on the SL function as a phytohormone and tried to find new chemicals mimicking the hormonal action of SL by screening chemicals that inhibit branching of rice d10-1 mutant. Fortunately, we found 5-(4-chlorophenoxy)-3-methylfuran-2(5H)-one (3a) as a new chemical possessing SL-like activity against the rice d10-1 mutant. Then, we prepared several derivatives of 3a (3b-3k) to examine their ability to inhibit shoot branching of rice d10-1. These derivatives were synthesized by a one-pot coupling reaction between phenols and halo butenolide to give 5-phenoxy 3-methylfuran-2(5H)-one (3) derivatives, which possess a common substructure with SLs. Some of the derivatives showed SL-like activity more potently than GR24, a typical SL derivative, in a rice assay. As SLs also show activity by inducing seed germination of root parasitic plants, the induction activity of these derivatives was also evaluated. Here we report the structure-activity relationships of these compounds. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.019

文献信息

• NOVEL COMPOUND HAVING STRIGOLACTONE-LIKE ACTIVITY AND USE THEREOF
  申请人：Riken

  公开号：EP2623502A1

  公开（公告）日：2013-08-07

  The present invention provides a compound that has an activity equal to or higher than that of natural strigolactone, can be chemically synthesized by a convenient step and at low cost, exhibits stability in environments, and has no or weak seed germination-promoting effect on plants of the genus Striga or Orobanche. Specifically, the present invention provides a compound represented by the general formula (III) or a salt thereof, wherein X represents a lower alkyl group or the like; Q represents a single bond or the like; and ring C represents a 6-membered ring represented by the formula (IVa) or the like wherein R1, R2, R3, and R4 each independently represent a carbon atom or the like, Z1 and Z2 are bonded to the ring atoms of ring C and each independently represent a hydrogen atom, a halogen atom, or the like, and the groups R5, R6, R7, Z3, Z4, and Z5 are as defined in the specification.

  本发明提供了一种化合物，其活性等同于或高于天然绞股蓝内酯，可通过简便的步骤以较低的成本化学合成，在环境中表现出稳定性，且对绞股蓝属或鄂伦春属植物无促进种子萌发作用或促进作用较弱。具体而言，本发明提供了通式（III）代表的化合物或其盐，其中 X 代表低级烷基或类似物；Q 代表单键或类似物；其中 R1、R2、R3 和 R4 各自独立地代表碳原子或类似物，Z1 和 Z2 与环 C 的环原子键合，各自独立地代表氢原子、卤素原子或类似物，基团 R5、R6、R7、Z3、Z4 和 Z5 如说明书中所定义。
• New branching inhibitors and their potential as strigolactone mimics in rice
  作者：Kosuke Fukui、Shinsaku Ito、Kotomi Ueno、Shinjiro Yamaguchi、Junko Kyozuka、Tadao Asami

  DOI：10.1016/j.bmcl.2011.06.019

  日期：2011.8

  Strigolactones (SLs) are rhizosphere communication chemicals. Recent studies of highly branched mutants revealed that SL or its metabolites work as a phytohormone to inhibit shoot branching. When SLs are exogenously applied to the rice d10-1 mutant that has a highly branched phenotype caused by a defect in the SL biosynthesis gene (CCD8), they inhibit tiller bud outgrowth (branching in rice) of the mutant. We focused our attention on the SL function as a phytohormone and tried to find new chemicals mimicking the hormonal action of SL by screening chemicals that inhibit branching of rice d10-1 mutant. Fortunately, we found 5-(4-chlorophenoxy)-3-methylfuran-2(5H)-one (3a) as a new chemical possessing SL-like activity against the rice d10-1 mutant. Then, we prepared several derivatives of 3a (3b-3k) to examine their ability to inhibit shoot branching of rice d10-1. These derivatives were synthesized by a one-pot coupling reaction between phenols and halo butenolide to give 5-phenoxy 3-methylfuran-2(5H)-one (3) derivatives, which possess a common substructure with SLs. Some of the derivatives showed SL-like activity more potently than GR24, a typical SL derivative, in a rice assay. As SLs also show activity by inducing seed germination of root parasitic plants, the induction activity of these derivatives was also evaluated. Here we report the structure-activity relationships of these compounds. (C) 2011 Elsevier Ltd. All rights reserved.