(S,2E,7E,12E)-10-((tert-butyldimethylsilyl)oxy)-13-iodo-3,12-dimethyl-1-phenyltrideca-2,7,12-trien-6-one | 1394247-76-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S,2E,7E,12E)-10-((tert-butyldimethylsilyl)oxy)-13-iodo-3,12-dimethyl-1-phenyltrideca-2,7,12-trien-6-one
• CAS: 1394247-76-7
• 化学式: C₂₇H₄₁IO₂Si
• 分子量: 552.611
• InChiKey: XQYAOUFDWSIGDP-FOCOHADESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.59
• 重原子数：
  31.0
• 可旋转键数：
  12.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  甲醇 、 (S,2E,7E,12E)-10-((tert-butyldimethylsilyl)oxy)-13-iodo-3,12-dimethyl-1-phenyltrideca-2,7,12-trien-6-one 在 camphor-10-sulfonic acid 作用下， 反应 3.0h， 以53%的产率得到(2S,4S,6R)-6-((E)-3-iodo-2-methylallyl)-2,4-dimethoxy-2-((E)-3-methyl-5-phenylpent-3-en-1-yl)tetrahydro-2H-pyran
  参考文献：
  名称：

  Total Synthesis of Ripostatin A

  摘要：

  The first total synthesis of the bacterial RNA-polymerase inhibitor ripostatin A (1) was achieved. The route utilizes a cyclic methyl acetal intermediate and a sequence of a double Stifle cross-coupling reaction followed by a ring-closing metathesis for the construction of the macrolactone ring. Additionally, an unprecedented formation of the 4-methoxy substituted tetrahydropyrans was observed during the acid catalyzed acetalization of the beta,delta-dihydroxyketone.

  DOI：

  10.1021/ol302219x
• 作为产物：
  描述：

  (E)-5-methyl-7-phenylhept-5-en-2-one 在 三乙胺 、 N,N'-二环己基碳二亚胺 、 (-)-diisopinocamphenylborane chloride 、 copper(l) chloride 作用下， 以 乙醚 为溶剂， 反应 2.5h， 生成 (S,2E,7E,12E)-10-((tert-butyldimethylsilyl)oxy)-13-iodo-3,12-dimethyl-1-phenyltrideca-2,7,12-trien-6-one
  参考文献：
  名称：

  Total Synthesis of Ripostatin A

  摘要：

  The first total synthesis of the bacterial RNA-polymerase inhibitor ripostatin A (1) was achieved. The route utilizes a cyclic methyl acetal intermediate and a sequence of a double Stifle cross-coupling reaction followed by a ring-closing metathesis for the construction of the macrolactone ring. Additionally, an unprecedented formation of the 4-methoxy substituted tetrahydropyrans was observed during the acid catalyzed acetalization of the beta,delta-dihydroxyketone.

  DOI：

  10.1021/ol302219x