N-benzyl-3-benzyl-4-[4-(3-methyl-2-butenyloxy)phenyl]maleimide | 1030374-55-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-benzyl-3-benzyl-4-[4-(3-methyl-2-butenyloxy)phenyl]maleimide
• 英文别名: 1,3-Dibenzyl-4-[4-(3-methylbut-2-enoxy)phenyl]pyrrole-2,5-dione
• CAS: 1030374-55-0
• 化学式: C₂₉H₂₇NO₃
• 分子量: 437.538
• InChiKey: IEEGMCNMOQMOSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  N-benzyl-3-benzyl-4-[4-(3-methyl-2-butenyloxy)phenyl]maleimide 在 氢氧化钾 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 3.0h， 以81%的产率得到3-benzyl-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：

  1,3-Dibenzyl-4-bromopyrrole-2,5-dione 、 4-[(3-methyl-2-butenyloxy)phenyl]tributylstannane 在 四(三苯基膦)钯 作用下， 以93%的产率得到N-benzyl-3-benzyl-4-[4-(3-methyl-2-butenyloxy)phenyl]maleimide
  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

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.