(2E)-3-[2',4'-bis(methoxymethoxy)phenyl]-1-(2"-[(3-methylbut-2-en-1-yl)oxy]-4"-{[2-(trimethylsilyl)ethoxy]methoxy}phenyl)prop-2-en-1-one | 850868-89-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (2E)-3-[2',4'-bis(methoxymethoxy)phenyl]-1-(2"-[(3-methylbut-2-en-1-yl)oxy]-4"-{[2-(trimethylsilyl)ethoxy]methoxy}phenyl)prop-2-en-1-one
• 英文别名: (2E)-3-[2,4-bis(methoxymethoxy)phenyl]-1-(2-[(3-methylbut-2-en-1-yl)oxy]-4-{[2-(trimethylsilyl)ethoxy]methoxy}phenyl)prop-2-en-1-one；(E)-3-[2,4-bis(methoxymethoxy)phenyl]-1-[2-(3-methylbut-2-enoxy)-4-(2-trimethylsilylethoxymethoxy)phenyl]prop-2-en-1-one
• CAS: 850868-89-2
• 化学式: C₃₀H₄₂O₈Si
• 分子量: 558.744
• InChiKey: UGUROTRGBAXWIM-UKTHLTGXSA-N

物化性质

• 沸点：
  643.4±55.0 °C(Predicted)
• 密度：
  1.083±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.58
• 重原子数：
  39
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  81.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2E)-3-[2',4'-bis(methoxymethoxy)phenyl]-1-(2"-[(3-methylbut-2-en-1-yl)oxy]-4"-{[2-(trimethylsilyl)ethoxy]methoxy}phenyl)prop-2-en-1-one 在 盐酸 、 florisil 作用下， 以 四氢呋喃 、 异丙醇 、 甲苯 为溶剂， 反应 26.0h， 生成 摩查尔酮A
  参考文献：
  名称：

  The synthetic preparation of naturally-occurring aromatase inhibitors, morachalcone A, isogemichalcone B, and isogemichalcone C

  摘要：

  A convergent synthesis applicable to the preparation of oxidized prenylchalcones is reported that relies on key Claisen-Schmidt, Mitsunobu, and vinyl/benzyl Stille coupling operations. The synthetic strategy was applied towards the preparation of the natural products morachalcone A and isogemichalcones B & C, allowing their preparation in less than 10 steps and 6-8% overall yield. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.09.068
• 作为产物：
  描述：

  1-(2-羟基-4-{[2-(三甲基甲硅烷基)乙氧基]甲氧基}苯基)乙酮 在 氢氧化钾 、 potassium carbonate 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 36.0h， 生成 (2E)-3-[2',4'-bis(methoxymethoxy)phenyl]-1-(2"-[(3-methylbut-2-en-1-yl)oxy]-4"-{[2-(trimethylsilyl)ethoxy]methoxy}phenyl)prop-2-en-1-one
  参考文献：
  名称：

  A short synthesis of morachalcone A

  摘要：

  Advanced C-prenylated intermediates for three aromatase inhibitors, including morachalcone A, can be synthesized through a Claisen-Schmidt condensation followed by Florisil((R))-catalyzed [1,3]-sigma tropic rearrangement of a prenyl phenyl ether. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.01.174

文献信息

• A short synthesis of morachalcone A
  作者：Joseph J. Romano、Eduard Casillas

  DOI：10.1016/j.tetlet.2005.01.174

  日期：2005.3

  Advanced C-prenylated intermediates for three aromatase inhibitors, including morachalcone A, can be synthesized through a Claisen-Schmidt condensation followed by Florisil((R))-catalyzed [1,3]-sigma tropic rearrangement of a prenyl phenyl ether. (c) 2005 Elsevier Ltd. All rights reserved.
• The synthetic preparation of naturally-occurring aromatase inhibitors, morachalcone A, isogemichalcone B, and isogemichalcone C
  作者：Drew R. Brandt、Kristina M. Pannone、Joseph J. Romano、Eduard G. Casillas

  DOI：10.1016/j.tet.2013.09.068

  日期：2013.11

  A convergent synthesis applicable to the preparation of oxidized prenylchalcones is reported that relies on key Claisen-Schmidt, Mitsunobu, and vinyl/benzyl Stille coupling operations. The synthetic strategy was applied towards the preparation of the natural products morachalcone A and isogemichalcones B & C, allowing their preparation in less than 10 steps and 6-8% overall yield. (C) 2013 Elsevier Ltd. All rights reserved.