[4-(1,1-dimethyl-prop-2-ynyloxy)phenyl]acetic acid methyl ester | 1242080-36-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: [4-(1,1-dimethyl-prop-2-ynyloxy)phenyl]acetic acid methyl ester
• 英文别名: Methyl 2-[4-(2-methylbut-3-yn-2-yloxy)phenyl]acetate；methyl 2-[4-(2-methylbut-3-yn-2-yloxy)phenyl]acetate
• CAS: 1242080-36-9
• 化学式: C₁₄H₁₆O₃
• 分子量: 232.279
• InChiKey: MCMFRUJSEDTFGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  [4-(1,1-dimethyl-prop-2-ynyloxy)phenyl]acetic acid methyl ester 在 lithium aluminium tetrahydride 、 四溴化碳 、 三苯基膦 、 N,N-二乙基苯胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 2.25h， 生成 6-(2-bromoethyl)-2,2-dimethyl-2H-chromene
  参考文献：
  名称：

  New Class of Algicidal Compounds and Fungicidal Activities Derived from a Chromene Amide of Amyris texana

  摘要：

  A chromene amide, N-[2-(2,2-dimethyl-2H-1-benzopyran-6-yl)ethyl]-N,3-dimethylbutanamide, was isolated from the EtOAc extract of the leaves of Amyris texana and found to have moderate antifungal activity against Colletotrichum spp. and selective algicidal activity against Planktothrix perornata, a cyanobacterium (blue-green alga) that causes musty off-flavor in farm-raised channel catfish (Ictalurus punctatus). To improve the selective algicidal activity and provide water solubility, a series of chromene analogues were synthesized and evaluated for algicidal activity using a 96-well microplate rapid bioassay. In addition, the chromene analogues were evaluated for antifungal and phytotoxic activities. Hydrochloride salts of a chromene amine analogue showed improved water solubility and selectivity toward P. perornata with activity comparable to that of the naturally occurring chromene amide.

  DOI：

  10.1021/jf101626g
• 作为产物：
  描述：

  3-氯-3-甲基-1-丁炔 、 4-羟基苯乙酸甲酯 在 potassium carbonate 、 potassium iodide 作用下， 以 丙酮 为溶剂， 反应 48.0h， 以49.5%的产率得到[4-(1,1-dimethyl-prop-2-ynyloxy)phenyl]acetic acid methyl ester
  参考文献：
  名称：

  New Class of Algicidal Compounds and Fungicidal Activities Derived from a Chromene Amide of Amyris texana

  摘要：

  A chromene amide, N-[2-(2,2-dimethyl-2H-1-benzopyran-6-yl)ethyl]-N,3-dimethylbutanamide, was isolated from the EtOAc extract of the leaves of Amyris texana and found to have moderate antifungal activity against Colletotrichum spp. and selective algicidal activity against Planktothrix perornata, a cyanobacterium (blue-green alga) that causes musty off-flavor in farm-raised channel catfish (Ictalurus punctatus). To improve the selective algicidal activity and provide water solubility, a series of chromene analogues were synthesized and evaluated for algicidal activity using a 96-well microplate rapid bioassay. In addition, the chromene analogues were evaluated for antifungal and phytotoxic activities. Hydrochloride salts of a chromene amine analogue showed improved water solubility and selectivity toward P. perornata with activity comparable to that of the naturally occurring chromene amide.

  DOI：

  10.1021/jf101626g

文献信息

• New Class of Algicidal Compounds and Fungicidal Activities Derived from a Chromene Amide of Amyris texana
  作者：Kumudini M. Meepagala、Kevin K. Schrader、Charles L. Burandt、David E. Wedge、Stephen O. Duke

  DOI：10.1021/jf101626g

  日期：2010.9.8

  A chromene amide, N-[2-(2,2-dimethyl-2H-1-benzopyran-6-yl)ethyl]-N,3-dimethylbutanamide, was isolated from the EtOAc extract of the leaves of Amyris texana and found to have moderate antifungal activity against Colletotrichum spp. and selective algicidal activity against Planktothrix perornata, a cyanobacterium (blue-green alga) that causes musty off-flavor in farm-raised channel catfish (Ictalurus punctatus). To improve the selective algicidal activity and provide water solubility, a series of chromene analogues were synthesized and evaluated for algicidal activity using a 96-well microplate rapid bioassay. In addition, the chromene analogues were evaluated for antifungal and phytotoxic activities. Hydrochloride salts of a chromene amine analogue showed improved water solubility and selectivity toward P. perornata with activity comparable to that of the naturally occurring chromene amide.