(5aSR,7RS,8SR)-8-butyl-4,5,5a,6,7,8-hexahydro-7-methylcyclopenta[de]quinazolin-2-amine | 182266-75-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: (5aSR,7RS,8SR)-8-butyl-4,5,5a,6,7,8-hexahydro-7-methylcyclopenta[de]quinazolin-2-amine
• 英文别名: mirabilin B；(1S,9S,10R)-9-butyl-10-methyl-5,7-diazatricyclo[6.3.1.04,12]dodeca-4(12),5,7-trien-6-amine
• CAS: 182266-75-7
• 化学式: C₁₅H₂₃N₃
• 分子量: 245.368
• InChiKey: IECGAEWATGHTLG-VWYCJHECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  51.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (3aSR,5aSR,7RS,8SR)-8-butyl-1,3a,4,5,5a,6,7,8-octahydro-7-methylcyclopenta[de]quinazolin-2-amine 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以80%的产率得到(5aSR,7RS,8SR)-8-butyl-4,5,5a,6,7,8-hexahydro-7-methylcyclopenta[de]quinazolin-2-amine
  参考文献：
  名称：

  Synthesis of 7-Epineoptilocaulin, Mirabilin B, and Isoptilocaulin. A Unified Biosynthetic Proposal for the Ptilocaulin and Batzelladine Alkaloids. Synthesis and Structure Revision of Netamines E and G

  摘要：

  Addition of guanidine to a 6-methylhexahydroindenone in MeOH at 85 degrees C afforded 7-epineoptilocaulin. A similar reaction with a 6-propylhexahydroindenone afforded netamine E. MnO2 oxidation of 7-epineoptilocaulin and netamine E afforded mirabilin B and netamine G, respectively. The netamines have the side chains trans, not cis as was initially proposed. A unified biosynthetic scheme for the batzelladines and ptilocaulin family is proposed. Conjugate addition of guanidine to a bis enone followed by an intramolecular Michael reaction of the enolate to the other enone, aldol reaction, dehydration, and enamine formation will lead to a tricyclic intermediate at the dehydroptilocaulin oxidation state. 1,4-Hydride addition will lead to ptilocaulin or 7-epineoptilocaulin depending on which face the hydride adds to. 1,2-Hydride addition will lead to isoptilocaulin. The key tricyclic intermediate was prepared from a tetrahydroindenone and guanidine and reduced with NaBH4 to give a mixture rich in ptilocaulin and isoptilocaulin.

  DOI：

  10.1021/jo801956w

文献信息

• Synthesis of 7-Epineoptilocaulin, Mirabilin B, and Isoptilocaulin. A Unified Biosynthetic Proposal for the Ptilocaulin and Batzelladine Alkaloids. Synthesis and Structure Revision of Netamines E and G
  作者：Min Yu、Susan S. Pochapsky、Barry B. Snider

  DOI：10.1021/jo801956w

  日期：2008.11.21

  Addition of guanidine to a 6-methylhexahydroindenone in MeOH at 85 degrees C afforded 7-epineoptilocaulin. A similar reaction with a 6-propylhexahydroindenone afforded netamine E. MnO2 oxidation of 7-epineoptilocaulin and netamine E afforded mirabilin B and netamine G, respectively. The netamines have the side chains trans, not cis as was initially proposed. A unified biosynthetic scheme for the batzelladines and ptilocaulin family is proposed. Conjugate addition of guanidine to a bis enone followed by an intramolecular Michael reaction of the enolate to the other enone, aldol reaction, dehydration, and enamine formation will lead to a tricyclic intermediate at the dehydroptilocaulin oxidation state. 1,4-Hydride addition will lead to ptilocaulin or 7-epineoptilocaulin depending on which face the hydride adds to. 1,2-Hydride addition will lead to isoptilocaulin. The key tricyclic intermediate was prepared from a tetrahydroindenone and guanidine and reduced with NaBH4 to give a mixture rich in ptilocaulin and isoptilocaulin.