6-[1-hydroxy-3-(4-methoxyphenyl)allylidene]-2,2,4-tris(3-methylbut-2-enyl)cyclohex-4-ene-1,3-dione | 1001906-06-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 6-[1-hydroxy-3-(4-methoxyphenyl)allylidene]-2,2,4-tris(3-methylbut-2-enyl)cyclohex-4-ene-1,3-dione
• 英文别名: 5-O-methylmunchiwarin；(6Z)-6-[(E)-1-hydroxy-3-(4-methoxyphenyl)prop-2-enylidene]-2,2,4-tris(3-methylbut-2-enyl)cyclohex-4-ene-1,3-dione
• CAS: 1001906-06-4
• 化学式: C₃₁H₃₈O₄
• 分子量: 474.64
• InChiKey: YOYCBVJYHXRCJV-AMCKLSOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-[1-hydroxy-3-(4-methoxyphenyl)allylidene]-2,2,4-tris(3-methylbut-2-enyl)cyclohex-4-ene-1,3-dione 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以53%的产率得到munchiwarin
  参考文献：
  名称：

  Total Synthesis of Munchiwarin, a Triprenylated Chalcone from Crotalaria medicagenia

  摘要：

  efficient method is developed for the synthesis of the modified triprenylated chalcone, munchiwarin (1), isolated from the roots of Crotalaria medicagenia. The synthesis of 1 utilizes a Claisen-Schmidt condensation between 2,4-dihydroxy-3,5-C-diprenyl acetophenone and 4-methoxy benzaldehyde in the presence of Ba(OH)(2) to yield the unusual chalcone 5 that contains a nine-membered ether ring. Further prenylation of 5 with 1-bromo-3-methylbut-2-ene and its subsequent demethylation with BBr3 gave munchiwarin (1).

  DOI：

  10.1021/ol702187m
• 作为产物：
  描述：

  1-(2-hydroxy-6,6,7,9-tetramethyl-6,7,8,11-tetrahydro-5-oxabenzocyclononen-3-yl)-3-(4-methoxyphenyl)propenone 、 1-溴-3-甲基-2-丁烯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以95%的产率得到6-[1-hydroxy-3-(4-methoxyphenyl)allylidene]-2,2,4-tris(3-methylbut-2-enyl)cyclohex-4-ene-1,3-dione
  参考文献：
  名称：

  Total Synthesis of Munchiwarin, a Triprenylated Chalcone from Crotalaria medicagenia

  摘要：

  efficient method is developed for the synthesis of the modified triprenylated chalcone, munchiwarin (1), isolated from the roots of Crotalaria medicagenia. The synthesis of 1 utilizes a Claisen-Schmidt condensation between 2,4-dihydroxy-3,5-C-diprenyl acetophenone and 4-methoxy benzaldehyde in the presence of Ba(OH)(2) to yield the unusual chalcone 5 that contains a nine-membered ether ring. Further prenylation of 5 with 1-bromo-3-methylbut-2-ene and its subsequent demethylation with BBr3 gave munchiwarin (1).

  DOI：

  10.1021/ol702187m

文献信息

• Total Synthesis of Munchiwarin, a Triprenylated Chalcone from <i>Crotalaria medicagenia</i>
  作者：T. Narender、K. Papi Reddy、Shweta、Kumkum Srivastava、D. K. Mishra、S. K. Puri

  DOI：10.1021/ol702187m

  日期：2007.12.1

  efficient method is developed for the synthesis of the modified triprenylated chalcone, munchiwarin (1), isolated from the roots of Crotalaria medicagenia. The synthesis of 1 utilizes a Claisen-Schmidt condensation between 2,4-dihydroxy-3,5-C-diprenyl acetophenone and 4-methoxy benzaldehyde in the presence of Ba(OH)(2) to yield the unusual chalcone 5 that contains a nine-membered ether ring. Further prenylation of 5 with 1-bromo-3-methylbut-2-ene and its subsequent demethylation with BBr3 gave munchiwarin (1).