1H-咪唑-5-甲酰胺,4-羟基-1-[(4-硝基苯基)甲基]- | 28290-35-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: 1H-咪唑-5-甲酰胺,4-羟基-1-[(4-硝基苯基)甲基]-
• 英文名称: dehydrosaussurea lactone
• 英文别名: Dehydrosaussurealactone；(3aS,6S,7S,7aS)-6-ethenyl-6-methyl-3-methylidene-7-prop-1-en-2-yl-4,5,7,7a-tetrahydro-3aH-1-benzofuran-2-one
• CAS: 28290-35-9
• 化学式: C₁₅H₂₀O₂
• 分子量: 232.323
• InChiKey: ZNTHTBBAGNVESR-SFDCQRBFSA-N

物化性质

• 沸点：
  346.2±42.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1H-咪唑-5-甲酰胺,4-羟基-1-[(4-硝基苯基)甲基]- 在 platinum(IV) oxide N-溴代丁二酰亚胺(NBS) 、 氢气 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 反应 44.0h， 生成 1-Bromsantanolid
  参考文献：
  名称：

  Jain, Tikam C.; Banks, Calvin M., Canadian Journal of Chemistry, 1980, vol. 58, p. 447 - 449

  摘要：

  DOI：
• 作为产物：
  描述：

  木香烃内酯 在 palladium diacetate 作用下， 以 甲苯 为溶剂， 以18%的产率得到1H-咪唑-5-甲酰胺,4-羟基-1-[(4-硝基苯基)甲基]-
  参考文献：
  名称：

  Microwave-Assisted Rearrangement of Costunolide Catalyzed by Palladium(II)

  摘要：

  The structure of costunolide was modified before conducting the Cope rearrangement under thermal conditions. This modification was undertaken to block the highly reactive Michael acceptor α-methylene-γ-lactone, thus preventing side reactions at high temperatures. In this work, the reaction was performed under heating or microwave irradiation using costunolide, not its modified version. Rates of Cope reactions catalyzed by palladium(II) assisted by microwave were substantially enhanced. The rearrangements of costunolide to elemanolide, eudesmanolides, and germacranolide were catalyzed by palladium acetate, bis(benzonitrile)palladium dichloride, and a mixture of both organometallics. Rates of microwave promoted rearrangements of costunolide were six times faster than the reactions assisted by heating. The best success rate for elemanolide (7) was obtained using a mixture of Pd(OAc)2 and (NCPh)2PdCl2. In this case, compound 7 was obtained in a yield of 34%, while the other sesquiterpene lactones were formed only in trace amounts. The reaction products were isolated using semi-preparative high performance liquid chromatography and further purified through sequential analytical high performance liquid chromatography. Bioactivity profiles that used etiolated wheat coleoptiles were conducted for compounds 6, 7, and 9. The tested compounds presented very high phytotoxicity, with inhibition up to 97%.

  DOI：

  10.21577/0103-5053.20240038

文献信息

• Palladium II promoted rearrangement of germacranolides. Synthesis of (+)-stoebenolide and (+)-dehydromelitensin
  作者：Alejandro F. Barrero、J.Enrique Oltra、Míriam Álvarez

  DOI：10.1016/s0040-4039(97)10775-4

  日期：1998.3

  rearrangement to elemanolides. On the other hand, equimolecular amounts of the palladium complex transformed germacranolides into eudesmanolides. These phenomena provide a versatile procedure for the synthesis of eudesmanolides and elemanolides under relatively mild experimental conditions. Thus, (+)-stoebenolide and (+)-dehydromelitensin were alternatively synthesized starting out from (+)-salonitenolide

  催化量的氯化双（苄腈）钯（II）可以提高germ草内酯的反应速率，应对重排成电子杀螨醇。另一方面，等摩尔量的钯络合物将germ草内酯转化为马来酸内酯。这些现象为在相对温和的实验条件下合成阿德曼香皂苷和电子香茅素提供了一种通用的方法。因此，交替地从（+）-salonitenolide开始合成（+）-硬皮烯内酯和（+）-脱氢melitensin。
• Plant enzymes for bioconversion
  申请人：Bouwmeester Jan Hendrik

  公开号：US20050019882A1

  公开（公告）日：2005-01-27

  The invention provides the use of enzymes derived from plants in biocatalysis. The regio- and stercoselective introduction of an oxygen group into an unactivated organic compound is still a largely unresolved challenge to organic chemistry (Faber, 2000). We have shown that enzymes of Asteraceae species are capable of converting with high regio- and stereospecificity for example sesquiterpene olefins to commercially interesting products.

  本发明提供了植物来源酶在生物催化中的应用。将氧基引入未活化有机化合物中的区域和立体选择性仍然是有机化学中一个基本未解决的挑战（Faber，2000）。我们已经证明，菊科物种的酶能够高度区域和立体特异性地将倍半萜烯烃等转化为商业上有趣的产物。
• Jain, Tikam C.; Banks, Calvin M., Canadian Journal of Chemistry, 1980, vol. 58, p. 447 - 449
  作者：Jain, Tikam C.、Banks, Calvin M.

  DOI：——

  日期：——
• Microwave-Assisted Rearrangement of Costunolide Catalyzed by Palladium(II)
  作者：Francisco Macías、Elson Alvarenga、Juan Galindo、José Molinillo、Cristiane Cerceau

  DOI：10.21577/0103-5053.20240038

  日期：——

  The structure of costunolide was modified before conducting the Cope rearrangement under thermal conditions. This modification was undertaken to block the highly reactive Michael acceptor α-methylene-γ-lactone, thus preventing side reactions at high temperatures. In this work, the reaction was performed under heating or microwave irradiation using costunolide, not its modified version. Rates of Cope reactions catalyzed by palladium(II) assisted by microwave were substantially enhanced. The rearrangements of costunolide to elemanolide, eudesmanolides, and germacranolide were catalyzed by palladium acetate, bis(benzonitrile)palladium dichloride, and a mixture of both organometallics. Rates of microwave promoted rearrangements of costunolide were six times faster than the reactions assisted by heating. The best success rate for elemanolide (7) was obtained using a mixture of Pd(OAc)2 and (NCPh)2PdCl2. In this case, compound 7 was obtained in a yield of 34%, while the other sesquiterpene lactones were formed only in trace amounts. The reaction products were isolated using semi-preparative high performance liquid chromatography and further purified through sequential analytical high performance liquid chromatography. Bioactivity profiles that used etiolated wheat coleoptiles were conducted for compounds 6, 7, and 9. The tested compounds presented very high phytotoxicity, with inhibition up to 97%.