1-benzyl-3-isobutyl-4-[4-(3-methylbut-2-enyloxy)phenyl]pyrrole-2,5-dione | 935525-81-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-benzyl-3-isobutyl-4-[4-(3-methylbut-2-enyloxy)phenyl]pyrrole-2,5-dione
• 英文别名: N-benzyl-3-isobutyl-4-[4-(3-methyl-2-butenyloxy)phenyl]maleimide；1-Benzyl-3-[4-(3-methylbut-2-enoxy)phenyl]-4-(2-methylpropyl)pyrrole-2,5-dione
• CAS: 935525-81-8
• 化学式: C₂₆H₂₉NO₃
• 分子量: 403.521
• InChiKey: NYIWMKUZPASAKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-benzyl-3-isobutyl-4-[4-(3-methylbut-2-enyloxy)phenyl]pyrrole-2,5-dione 在 氢氧化钾 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 3.0h， 以92%的产率得到3-isobutyl-4-[4-(3-methyl-2-butenyloxy)phenyl]furan-2,5-dione
  参考文献：
  名称：

  Total synthesis of (±)-camphorataimides and (±)-himanimides by NaBH4/Ni(OAc)2 or Zn/AcOH stereoselective reduction

  摘要：

  Maleic anhydride 1 of Antrodia camphorate, which can be isolated from Chinese herbal medicine, is achieved in which the longest linear sequence is only five steps, in 40% overall yield from commercially available succinic anhydride. The crucial antrodimides 3 and 2 can be readily transformed by the chemoselective reduction with Zn/AcOH and NaBH(4)/Ni(OAc)(2).4H(2)O to afford the naturally occurring camphorataimides, 4 and 5, in high yields as well, respectively. This synthetic strategy can also be modified to give access to a variety of different maleic acid derivatives, himanimides 6-8. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.02.077
• 作为产物：
  描述：

  1H-吡咯-2,5-二酮,3,4-二氯-1-(苯基甲基)- 在 tris(dibenzylideneacetone)dipalladium (0) N-甲基二环己基胺 、 三苯基膦 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 30.0h， 生成 1-benzyl-3-isobutyl-4-[4-(3-methylbut-2-enyloxy)phenyl]pyrrole-2,5-dione
  参考文献：
  名称：

  A concise synthesis of maleic anhydride and maleimide natural products found in Antrodia camphorata

  摘要：

  Recently, the natural products maleic anhydride I and maleimides 2 and 3 have been isolated from the mycelium of Antrodia Camphorata, each displaying activity in LLC cell lines. We describe a concise synthesis of each of these natural compounds utilizing C-C cross-coupling methodology, namely, the Negishi and Suzuki reactions. This efficient and high yielding synthesis is convergent lending itself to production of medicinal analogues. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.01.169

文献信息

• Total synthesis of (±)-camphorataimides and (±)-himanimides by NaBH4/Ni(OAc)2 or Zn/AcOH stereoselective reduction
  作者：Chia-Fu Cheng、Zhen-Chang Lai、Yean-Jang Lee

  DOI：10.1016/j.tet.2008.02.077

  日期：2008.5

  Maleic anhydride 1 of Antrodia camphorate, which can be isolated from Chinese herbal medicine, is achieved in which the longest linear sequence is only five steps, in 40% overall yield from commercially available succinic anhydride. The crucial antrodimides 3 and 2 can be readily transformed by the chemoselective reduction with Zn/AcOH and NaBH(4)/Ni(OAc)(2).4H(2)O to afford the naturally occurring camphorataimides, 4 and 5, in high yields as well, respectively. This synthetic strategy can also be modified to give access to a variety of different maleic acid derivatives, himanimides 6-8. (c) 2008 Elsevier Ltd. All rights reserved.
• A concise synthesis of maleic anhydride and maleimide natural products found in Antrodia camphorata
  作者：Scott G. Stewart、Marta E. Polomska、Rou Wei Lim

  DOI：10.1016/j.tetlet.2007.01.169

  日期：2007.3

  Recently, the natural products maleic anhydride I and maleimides 2 and 3 have been isolated from the mycelium of Antrodia Camphorata, each displaying activity in LLC cell lines. We describe a concise synthesis of each of these natural compounds utilizing C-C cross-coupling methodology, namely, the Negishi and Suzuki reactions. This efficient and high yielding synthesis is convergent lending itself to production of medicinal analogues. (c) 2007 Elsevier Ltd. All rights reserved.