(1S)-(1α,3α,4β)-4-butyl-5-oxo-3-propylcyclohexanepropanal | 1079832-45-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S)-(1α,3α,4β)-4-butyl-5-oxo-3-propylcyclohexanepropanal
• CAS: 1079832-45-3
• 化学式: C₁₆H₂₈O₂
• 分子量: 252.397
• InChiKey: QJXZOSBBAPKXBI-ZNMIVQPWSA-N

反应信息

• 作为产物：
  描述：

  (5S)-(3α,5α)-2-butyl-5-(3Z-hexenyl)-3-propylcyclohexanone 在 吡啶 、 臭氧 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (1S)-(1α,3α)-4-butyl-5-oxo-3-propylcyclohexanepropanal 、 (1S)-(1α,3α,4β)-4-butyl-5-oxo-3-propylcyclohexanepropanal
  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