12-[5-[5-[3-Chloro-1-tri(propan-2-yl)silylpyrrol-2-yl]-3-methoxyfuran-2-carbonyl]-1-diethoxyphosphorylpyrrol-2-yl]-2-methyldodecan-3-one | 1426385-20-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 12-[5-[5-[3-Chloro-1-tri(propan-2-yl)silylpyrrol-2-yl]-3-methoxyfuran-2-carbonyl]-1-diethoxyphosphorylpyrrol-2-yl]-2-methyldodecan-3-one
• 英文别名: 12-[5-[5-[3-chloro-1-tri(propan-2-yl)silylpyrrol-2-yl]-3-methoxyfuran-2-carbonyl]-1-diethoxyphosphorylpyrrol-2-yl]-2-methyldodecan-3-one
• CAS: 1426385-20-7
• 化学式: C₄₀H₆₄ClN₂O₇PSi
• 分子量: 779.47
• InChiKey: FRCXXQUCQMYEED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.38
• 重原子数：
  52
• 可旋转键数：
  24
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  12-[5-[5-[3-Chloro-1-tri(propan-2-yl)silylpyrrol-2-yl]-3-methoxyfuran-2-carbonyl]-1-diethoxyphosphorylpyrrol-2-yl]-2-methyldodecan-3-one 在 bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate 、 18-冠醚-6 、 bromotricarbonyl(tetrahydrofuran)rhenium(I) dimer 、 C₂₈H₄₈FeP₂ 、 氢气 、 双(三甲基硅烷基)氨基钾 、 zinc trifluoromethanesulfonate 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 、 1,2-二氯乙烷 、 甲苯 为溶剂， -78.0~70.0 ℃ 、10.0 MPa 条件下， 反应 49.0h， 生成 iso-roseophilin
  参考文献：
  名称：

  Modular Access to Complex Prodiginines: Total Synthesis of (+)-Roseophilin via its 2-Azafulvene Prototropisomer

  摘要：

  Ansa-bridged, prodiginines are bioactive pigments produced by bacteria. Certain of these structures are reported to be antagonists of protein protein interactions involved in apoptosis. We describe a new entry to alkaloids of this type, demonstrated with a concise asymmetric synthesis of (+)-roseophilin (3). Our route constructs the pyrrolophane motif via phosphoryl transfer-terminated macroaldolization and passes through a previously unexplored prototropic form of the natural product.

  DOI：

  10.1021/ja400473v
• 作为产物：
  描述：

  8-壬烯酸 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 sodium tetrahydroborate 、 t-butyldimethylsilane 、 palladium diacetate 、 四氯化钛 、 potassium hydride 、 三氟乙酸酐 、 三环己基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 1,2-二氯乙烷 、 异丙醇 、 甲苯 为溶剂， 60.0 ℃ 、101.33 kPa 条件下， 反应 88.0h， 生成 12-[5-[5-[3-Chloro-1-tri(propan-2-yl)silylpyrrol-2-yl]-3-methoxyfuran-2-carbonyl]-1-diethoxyphosphorylpyrrol-2-yl]-2-methyldodecan-3-one
  参考文献：
  名称：

  Modular Access to Complex Prodiginines: Total Synthesis of (+)-Roseophilin via its 2-Azafulvene Prototropisomer

  摘要：

  Ansa-bridged, prodiginines are bioactive pigments produced by bacteria. Certain of these structures are reported to be antagonists of protein protein interactions involved in apoptosis. We describe a new entry to alkaloids of this type, demonstrated with a concise asymmetric synthesis of (+)-roseophilin (3). Our route constructs the pyrrolophane motif via phosphoryl transfer-terminated macroaldolization and passes through a previously unexplored prototropic form of the natural product.

  DOI：

  10.1021/ja400473v

文献信息

• Modular Access to Complex Prodiginines: Total Synthesis of (+)-Roseophilin via its 2-Azafulvene Prototropisomer
  作者：James H. Frederich、Patrick G. Harran

  DOI：10.1021/ja400473v

  日期：2013.3.13

  Ansa-bridged, prodiginines are bioactive pigments produced by bacteria. Certain of these structures are reported to be antagonists of protein protein interactions involved in apoptosis. We describe a new entry to alkaloids of this type, demonstrated with a concise asymmetric synthesis of (+)-roseophilin (3). Our route constructs the pyrrolophane motif via phosphoryl transfer-terminated macroaldolization and passes through a previously unexplored prototropic form of the natural product.