methyl 2-(4-methoxyphenyl)-5-hydroxy-2,3-dihydro-1-benzofuran-4-carboxylate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: methyl 2-(4-methoxyphenyl)-5-hydroxy-2,3-dihydro-1-benzofuran-4-carboxylate
• 英文别名: methyl 5-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1-benzofuran-4-carboxylate
• 化学式: C₁₇H₁₆O₅
• 分子量: 300.311
• InChiKey: FAEVIWOTYWRMRP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2-(4-methoxyphenyl)-5-hydroxy-2,3-dihydro-1-benzofuran-4-carboxylate 在 盐酸 、 barium(II) hydroxide 作用下， 以 水 为溶剂， 生成 5-Hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1-benzofuran-4-carboxylic acid
  参考文献：
  名称：

  Synthesis and SAR of 2,3‐Dihydro‐1‐benzofuran‐4‐carboxylates: Potent Salicylic Acid‐Based Lead Structures against Plant Stress

  摘要：

  AbstractNew 2,3‐dihydro‐1‐benzofuran‐4‐carboxylic acid derivatives have been identified as potent lead structures against drought and cold stress in crops starting from the synthetic exploration of stabilized analogs of the natural product lunularic acid. An optimized Lewis‐acid mediated cyclization gave a short and efficient access to the envisaged 2,3‐dihydro‐1‐benzofuran‐4‐carboxylates. Enantioselective approaches were investigated to assess the potential impact of the chiral center on in vivo activity. Whilst 2,3‐dihydro‐1‐benzofuran‐4‐carboxamides and 2,3‐dihydro‐1‐benzofuran‐4‐carboxylates carrying phenyl substituents with electron‐withdrawing groups exhibited only low to moderate in vivo activity, the corresponding 2,3‐dihydro‐1‐benzofuran‐4‐carboxylates carrying optimized electron‐donating substituents in the phenyl moiety revealed strong in vivo activity, both against drought stress in several broad‐acre crops, as well as against cold stress in corn. Remarkably, several 2,3‐dihydro‐1‐benzofuran‐4‐carboxylates showed stronger efficacy than the internal standards used in our in vivo SAR study.

  DOI：

  10.1002/ejoc.202200087
• 作为产物：
  描述：

  2,5-二羟基苯甲酸甲酯 在 magnesium sulfate 、 silver(l) oxide 、 ytterbium(III) triflate 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 4.75h， 生成 methyl 2-(4-methoxyphenyl)-5-hydroxy-2,3-dihydro-1-benzofuran-4-carboxylate
  参考文献：
  名称：

  USE OF SUBSTITUTED 2,3-DIHYDRO-1-BENZOFURAN-4-CARBOXYLIC ACIDS OR SALTS THEREOF AS ACTIVE SUBSTANCES AGAINST ABIOTIC PLANT STRESS

  摘要：

  使用通式（I）或其盐代替2,3-二氢-1-苯并呋喃-4-羧酸，其中通式（I）中的基团如描述中定义的，用于增加植物对非生物胁迫的耐受性，促进植物生长和/或增加植物产量，并用于制备上述化合物的特定过程。

  公开号：

  US20150322094A1

文献信息

• USE OF SUBSTITUTED 2,3-DIHYDRO-1-BENZOFURAN-4-CARBOXYLIC ACIDS OR SALTS THEREOF AS ACTIVE SUBSTANCES AGAINST ABIOTIC PLANT STRESS
  申请人：Bayer CropScience AG

  公开号：US20150322094A1

  公开（公告）日：2015-11-12

  Use of substituted 2,3-dihydro-1-benzofuran-4-carboxylic acids of the general formula (I) or salts thereof where the radicals in the general formula (I) are as defined in the description, for increasing stress tolerance in plants with respect to abiotic stress, for enhancing plant growth and/or for increasing plant yield, and specific processes for preparing the aforementioned compounds.

  使用通式（I）或其盐代替2,3-二氢-1-苯并呋喃-4-羧酸，其中通式（I）中的基团如描述中定义的，用于增加植物对非生物胁迫的耐受性，促进植物生长和/或增加植物产量，并用于制备上述化合物的特定过程。
• Asano, Jun; Ryu, Yukiko; Chiba, Kazuhiro, Journal of Chemical Research, Miniprint, 1995, # 4, p. 862 - 877
  作者：Asano, Jun、Ryu, Yukiko、Chiba, Kazuhiro、Tada, Masahiro

  DOI：——

  日期：——
• VERWENDUNG SUBSTITUIERTER 2,3-DIHYDRO-1-BENZOFURAN-4-CARBONSÄUREN ODER DEREN SALZE ALS WIRKSTOFFE GEGEN ABIOTISCHEN PFLANZENSTRESS
  申请人：Bayer CropScience AG

  公开号：EP2892343A1

  公开（公告）日：2015-07-15
• [DE] VERWENDUNG SUBSTITUIERTER 2,3-DIHYDRO-1-BENZOFURAN-4-CARBONSÄUREN ODER DEREN SALZE ALS WIRKSTOFFE GEGEN ABIOTISCHEN PFLANZENSTRESS<br/>[EN] USE OF SUBSTITUTED 2,3-DIHYDRO-1-BENZOFURAN-4-CARBOXYLIC ACIDS OR SALTS THEREOF AS ACTIVE SUBSTANCES AGAINST ABIOTIC PLANT STRESS<br/>[FR] UTILISATION D'ACIDE 2,3-DIHYDRO-1-BENZOFURANE-4-CARBOXYLIQUE SUBSTITUÉ OU DE SES SELS COMME PRINCIPES ACTIFS CONTRE LE STRESS ABIOTIQUE DES PLANTES
  申请人：BAYER CROPSCIENCE AG

  公开号：WO2014037349A1

  公开（公告）日：2014-03-13

  Verwendung substituierter 2,3-Dihydro-1-benzofuran-4-carbonsäuren der allgemeinen Formel (I) oder deren Salze wobei die Reste in der allgemeinen Formel (I) den in der Beschreibung gegebenen Definitionen entsprechen, zur Steigerung der Stresstoleranz in Pflanzen gegenüber abiotischem Stress, zur Stärkung des Pflanzenwachstums und/oder zur Erhöhung des Pflanzenertrags, sowie spezielle Verfahren zur Herstellung der vorgenannten Verbindungen
• Synthesis and SAR of 2,3‐Dihydro‐1‐benzofuran‐4‐carboxylates: Potent Salicylic Acid‐Based Lead Structures against Plant Stress
  作者：Guido Bojack、Ronald W. Brown、Jan Dittgen、Ines Heinemann、Hendrik Helmke、Martin J. Hills、Sabine Hohmann、Philipp M. Holstein、Dirk Schmutzler、Jens Frackenpohl

  DOI：10.1002/ejoc.202200087

  日期：2022.4.12

  AbstractNew 2,3‐dihydro‐1‐benzofuran‐4‐carboxylic acid derivatives have been identified as potent lead structures against drought and cold stress in crops starting from the synthetic exploration of stabilized analogs of the natural product lunularic acid. An optimized Lewis‐acid mediated cyclization gave a short and efficient access to the envisaged 2,3‐dihydro‐1‐benzofuran‐4‐carboxylates. Enantioselective approaches were investigated to assess the potential impact of the chiral center on in vivo activity. Whilst 2,3‐dihydro‐1‐benzofuran‐4‐carboxamides and 2,3‐dihydro‐1‐benzofuran‐4‐carboxylates carrying phenyl substituents with electron‐withdrawing groups exhibited only low to moderate in vivo activity, the corresponding 2,3‐dihydro‐1‐benzofuran‐4‐carboxylates carrying optimized electron‐donating substituents in the phenyl moiety revealed strong in vivo activity, both against drought stress in several broad‐acre crops, as well as against cold stress in corn. Remarkably, several 2,3‐dihydro‐1‐benzofuran‐4‐carboxylates showed stronger efficacy than the internal standards used in our in vivo SAR study.