N-benzyl-3-bromo-4-isobutylmaleimide | 935525-83-0

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: N-benzyl-3-bromo-4-isobutylmaleimide
• 英文别名: 1-Benzyl-3-bromo-4-(2-methylpropyl)pyrrole-2,5-dione
• CAS: 935525-83-0
• 化学式: C₁₅H₁₆BrNO₂
• 分子量: 322.202
• InChiKey: MAEVJWAFZVJTKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-benzyl-3-bromo-4-isobutylmaleimide 在 tris(dibenzylideneacetone)dipalladium (0) 吡啶 、 氢氧化钾 、 N-甲基二环己基胺 、 盐酸羟胺 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 为溶剂， 反应 27.0h， 生成 3-isobutyl-4-[4-(3-methyl-2-butenyloxy)phenyl]-1H-pyrrol-1-ol-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
• 作为产物：
  描述：

  N-benzyl-3-bromomaleimide 在 bis(triphenylphosphine)nickel(II) chloride 、 aluminum tri-bromide 溴 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 N-benzyl-3-bromo-4-isobutylmaleimide
  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.