4-(tert-butyldimethylsilyloxy)-11-(1-(tert-butyldimethylsilyloxy)allyl)-9-methoxy-7-methyl-4,5-dihydrophenanthro[1,2-c]furan-1(3H)-one | 1256812-07-3

• 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-4,5-dihydrophenanthro[1,2-c]furan-1(3H)-one
• 英文别名: 4-[tert-butyl(dimethyl)silyl]oxy-11-[1-[tert-butyl(dimethyl)silyl]oxyprop-2-enyl]-9-methoxy-7-methyl-4,5-dihydro-3H-naphtho[2,1-e][2]benzofuran-1-one
• CAS: 1256812-07-3
• 化学式: C₃₃H₄₈O₅Si₂
• 分子量: 580.912
• InChiKey: YPUSCOOEWQRLHR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.21
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  4-(tert-butyldimethylsilyloxy)-5-(2-ethynyl-3-methoxy-5-methylphenyl)pent-2-ynyl 4-(tert-butyldimethylsilyloxy)hex-5-en-2-ynoate 在 Wilkinson's catalyst 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 4-(tert-butyldimethylsilyloxy)-11-(1-(tert-butyldimethylsilyloxy)allyl)-9-methoxy-7-methyl-4,5-dihydrophenanthro[1,2-c]furan-1(3H)-one
  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.