methyl (E)-4-[(1,3-dihydro-7-hydroxy-4,6-dimethyl-1-oxo-5-isobenzofuranyl)oxy]-2-methyl-2-butenoate | 1065231-07-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 英文名称: methyl (E)-4-[(1,3-dihydro-7-hydroxy-4,6-dimethyl-1-oxo-5-isobenzofuranyl)oxy]-2-methyl-2-butenoate
• 英文别名: methyl (E)-4-[(7-hydroxy-4,6-dimethyl-1-oxo-3H-2-benzofuran-5-yl)oxy]-2-methylbut-2-enoate
• CAS: 1065231-07-3
• 化学式: C₁₆H₁₈O₆
• 分子量: 306.315
• InChiKey: YETVZMFOWJUVNL-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (E)-4-[(1,3-dihydro-7-hydroxy-4,6-dimethyl-1-oxo-5-isobenzofuranyl)oxy]-2-methyl-2-butenoate 在 lithium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 6.0h， 以99%的产率得到(E)-5-(3-carboxy-2-butenyloxy)-7-hydroxy-4,6-dimethylphthalide
  参考文献：
  名称：

  Synthesis of novel antifungal phthalides produced by a wheat rhizosphere fungus

  摘要：

  Two antifungal phthalides produced by a wheat rhizosphere fungus have been synthesized using the Alder-Rickert reaction to construct their common isobenzofuranone core structure. The absolute configuration of one of the two phthalides has been determined to be S by synthesizing its (S)- and (R)-enantiomer and comparing their optical rotations with that of the natural product. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.07.023
• 作为产物：
  描述：

  methyl (E)-4-[(1,3-dihydro-7-methoxy-4,6-dimethyl-1-oxo-5-isobenzofuranyl)oxy]-2-methyl-2-butenoate 在 magnesium iodide 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 2.5h， 以60%的产率得到methyl (E)-4-[(1,3-dihydro-7-hydroxy-4,6-dimethyl-1-oxo-5-isobenzofuranyl)oxy]-2-methyl-2-butenoate
  参考文献：
  名称：

  Synthesis of novel antifungal phthalides produced by a wheat rhizosphere fungus

  摘要：

  Two antifungal phthalides produced by a wheat rhizosphere fungus have been synthesized using the Alder-Rickert reaction to construct their common isobenzofuranone core structure. The absolute configuration of one of the two phthalides has been determined to be S by synthesizing its (S)- and (R)-enantiomer and comparing their optical rotations with that of the natural product. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.07.023