2-(8-nonenyl)pyrrole | 1213263-05-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-(8-nonenyl)pyrrole
• 英文别名: 2-(non-8-enyl)-1H-pyrrole；2-non-8-enyl-1H-pyrrole
• CAS: 1213263-05-8
• 化学式: C₁₃H₂₁N
• 分子量: 191.316
• InChiKey: PMPCRYKPKOUKLB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2-(8-nonenyl)pyrrole 在 四氯化钛 、 potassium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 6.0h， 生成 diethyl (2-(5-(3-chloro-1-(triisopropylsilyl)-1H-pyrrol-2-yl)-3-methoxyfuran-2-ylcarbonyl)-5-(non-8-en-1-yl)-1H-pyrrol-1-yl)phosphonate
  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 sodium tetrahydroborate 、 三氟乙酸酐 作用下， 以 1,2-二氯乙烷 、 异丙醇 为溶剂， 反应 74.0h， 生成 2-(8-nonenyl)pyrrole
  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

• Evaluation of the Biosynthetic Proposal for the Synthesis of Marineosins A and B
  作者：Leslie N. Aldrich、Eric S. Dawson、Craig W. Lindsley

  DOI：10.1021/ol100034p

  日期：2010.3.5

  The first synthetic efforts toward marineosins A and B, novel spiroaminals from a Streptomyces actinomycete, are described by evaluation of the proposed biosynthesis. The hypothesized biosynthetic C1-C25 Diels-Alder substrate was prepared in 8 steps in 5.1% overall yield; however, the proposed biomimetic inverse-electron-demand hetero-Diels-Alder reaction failed to deliver the marineosin core. Molecular mechanics supports this observation.
• 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.