4-(tert-butyldimethylsilyloxy)-11-(1-(tert-butyldimethylsilyloxy)allyl)-9-methoxy-7-methyl-1-vinyl-1,3,4,5-tetrahydrophenanthro[1,2-c]furan-1-ol | 1256812-08-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 4-(tert-butyldimethylsilyloxy)-11-(1-(tert-butyldimethylsilyloxy)allyl)-9-methoxy-7-methyl-1-vinyl-1,3,4,5-tetrahydrophenanthro[1,2-c]furan-1-ol
• 英文别名: 4-[tert-butyl(dimethyl)silyl]oxy-11-[1-[tert-butyl(dimethyl)silyl]oxyprop-2-enyl]-1-ethenyl-9-methoxy-7-methyl-4,5-dihydro-3H-naphtho[2,1-e][2]benzofuran-1-ol
• CAS: 1256812-08-4
• 化学式: C₃₅H₅₂O₅Si₂
• 分子量: 608.966
• InChiKey: XPYSCYDLHWFOBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  42
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(tert-butyldimethylsilyloxy)-11-(1-(tert-butyldimethylsilyloxy)allyl)-9-methoxy-7-methyl-1-vinyl-1,3,4,5-tetrahydrophenanthro[1,2-c]furan-1-ol 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 2,6-二氯-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以77%的产率得到((7-methoxy-9-methyl-11,12-dihydro-1H-tetrapheno[8,7-bc]furan-5,12-diyl)bis(oxy))bis(tert-butyldimethylsilane)
  参考文献：
  名称：

  Synthesis of the Landomycinone Skeleton

  摘要：

  The synthesis of the highly functionalized tetracyclic skeleton of landomycinone (2), the aglycon of landomycins, was performed using two pivotal steps relying on metal-catalyzed reactions. They are (1) a [2 + 2 + 2] cycloaddition of alkynes promoted by Wilkinson's catalyst to build rings B and C concomitantly and (2) a ring-closing metathesis followed by aromatization to build ring D.

  DOI：

  10.1021/jo1018377
• 作为产物：
  描述：

  溴乙烯 、 4-(tert-butyldimethylsilyloxy)-11-(1-(tert-butyldimethylsilyloxy)allyl)-9-methoxy-7-methyl-4,5-dihydrophenanthro[1,2-c]furan-1(3H)-one 在 叔丁基锂 作用下， 以 四氢呋喃 、 乙醚 、 正戊烷 为溶剂， 反应 0.5h， 以93%的产率得到4-(tert-butyldimethylsilyloxy)-11-(1-(tert-butyldimethylsilyloxy)allyl)-9-methoxy-7-methyl-1-vinyl-1,3,4,5-tetrahydrophenanthro[1,2-c]furan-1-ol
  参考文献：
  名称：

  Synthesis of the Landomycinone Skeleton

  摘要：

  The synthesis of the highly functionalized tetracyclic skeleton of landomycinone (2), the aglycon of landomycins, was performed using two pivotal steps relying on metal-catalyzed reactions. They are (1) a [2 + 2 + 2] cycloaddition of alkynes promoted by Wilkinson's catalyst to build rings B and C concomitantly and (2) a ring-closing metathesis followed by aromatization to build ring D.

  DOI：

  10.1021/jo1018377

文献信息

• Synthesis of the Landomycinone Skeleton
  作者：Xavier Bugaut、Xavier Guinchard、Emmanuel Roulland

  DOI：10.1021/jo1018377

  日期：2010.12.3

  The synthesis of the highly functionalized tetracyclic skeleton of landomycinone (2), the aglycon of landomycins, was performed using two pivotal steps relying on metal-catalyzed reactions. They are (1) a [2 + 2 + 2] cycloaddition of alkynes promoted by Wilkinson's catalyst to build rings B and C concomitantly and (2) a ring-closing metathesis followed by aromatization to build ring D.