dihydro-roseophilin | 1426385-25-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dihydro-roseophilin
• 英文别名: (12R,13R,15S)-15-[5-(3-chloro-1H-pyrrol-2-yl)-3-methoxyfuran-2-yl]-13-propan-2-yl-2-azatricyclo[10.2.1.13,14]hexadeca-1(14),3(16)-diene
• CAS: 1426385-25-2
• 化学式: C₂₇H₃₅ClN₂O₂
• 分子量: 455.04
• InChiKey: NQEMTCYBLYGTLM-QFWMQHCXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  54
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  dihydro-roseophilin 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以72%的产率得到(+)-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) 、 bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate 、 sodium tetrahydroborate 、 18-冠醚-6 、 bromotricarbonyl(tetrahydrofuran)rhenium(I) dimer 、 t-butyldimethylsilane 、 C₂₈H₄₈FeP₂ 、 氢气 、 palladium diacetate 、 四氯化钛 、 potassium hydride 、 双(三甲基硅烷基)氨基钾 、 zinc trifluoromethanesulfonate 、 三氟乙酸酐 、 三环己基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙酸乙酯 、 1,2-二氯乙烷 、 异丙醇 、 甲苯 为溶剂， -78.0~70.0 ℃ 、10.0 MPa 条件下， 反应 141.0h， 生成 dihydro-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

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.