methyl 4-prenyloxyphenylacetate | 1411884-59-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: methyl 4-prenyloxyphenylacetate
• 英文别名: Methyl 2-[4-(3-methylbut-2-enoxy)phenyl]acetate；methyl 2-[4-(3-methylbut-2-enoxy)phenyl]acetate
• CAS: 1411884-59-7
• 化学式: C₁₄H₁₈O₃
• 分子量: 234.295
• InChiKey: NRNZDRAYSDSWIV-UHFFFAOYSA-N

物化性质

• 沸点：
  329.4±22.0 °C(Predicted)
• 密度：
  1.038±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 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：

  methyl 4-prenyloxyphenylacetate 在 N-甲基吡咯烷酮 、 iron(III)-acetylacetonate 、 potassium tert-butylate 、 水 、 二甲基二环氧乙烷 、 戴斯-马丁氧化剂 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 53.92h， 生成 3-isobutyl-4-[4-(3-methyl-2-butenyloxy)phenyl]furan-2,5-dione
  参考文献：
  名称：

  Unified route to asymmetrically substituted butenolide, maleic anhydride, and maleimide constituents of Antrodia camphorata

  摘要：

  The first synthesis of antrocinnamomin D and a new synthesis of antrodins A and B have been achieved in 6-8 steps and high overall efficiency (51, 46, and 43%, respectively) from commercially available methyl 4-hydroxyphenylacetate. Key steps include Furstner-Kochi iron-catalyzed sp(2)-sp(3) cross-coupling and 2-silyloxyfuran oxyfunctionalization. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.09.064
• 作为产物：
  描述：

  4-羟基苯乙酸甲酯 、 1-溴-3-甲基-2-丁烯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 17.25h， 以97%的产率得到methyl 4-prenyloxyphenylacetate
  参考文献：
  名称：

  Unified route to asymmetrically substituted butenolide, maleic anhydride, and maleimide constituents of Antrodia camphorata

  摘要：

  The first synthesis of antrocinnamomin D and a new synthesis of antrodins A and B have been achieved in 6-8 steps and high overall efficiency (51, 46, and 43%, respectively) from commercially available methyl 4-hydroxyphenylacetate. Key steps include Furstner-Kochi iron-catalyzed sp(2)-sp(3) cross-coupling and 2-silyloxyfuran oxyfunctionalization. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.09.064

文献信息

• Unified route to asymmetrically substituted butenolide, maleic anhydride, and maleimide constituents of Antrodia camphorata
  作者：John Boukouvalas、Vincent Albert、Richard P. Loach、Raphaël Lafleur-Lambert

  DOI：10.1016/j.tet.2012.09.064

  日期：2012.11

  The first synthesis of antrocinnamomin D and a new synthesis of antrodins A and B have been achieved in 6-8 steps and high overall efficiency (51, 46, and 43%, respectively) from commercially available methyl 4-hydroxyphenylacetate. Key steps include Furstner-Kochi iron-catalyzed sp(2)-sp(3) cross-coupling and 2-silyloxyfuran oxyfunctionalization. (c) 2012 Elsevier Ltd. All rights reserved.
• Biomimetic Synthesis of Antrodia Maleimides and Maleic Anhydrides
  作者：John Boukouvalas、Vincent Albert

  DOI：10.3987/com-13-s(s)92

  日期：——

  A simple and efficient biomimetic synthesis of Antrodia maleimides and maleic anhydrides, including the HCV protease inhibitor antrodin A, is described. The key step is a Perkin-type condensation performed under exceptionally mild conditions.