(5β,6α,7aβ)-5-butyl-1,2,5,6,7,7a-hexahydro-6-methyl-4H-inden-4-one | 86509-61-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5β,6α,7aβ)-5-butyl-1,2,5,6,7,7a-hexahydro-6-methyl-4H-inden-4-one
• CAS: 86509-61-7；86509-62-8；88525-26-2；88586-84-9；88586-88-3；88586-89-4；105930-29-8；105930-30-1；131100-63-5；131100-64-6
• 化学式: C₁₄H₂₂O
• 分子量: 206.328
• InChiKey: MDIAFJQMDFHRLH-WIKAKEFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.74
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (5β,6α,7aβ)-5-butyl-1,2,5,6,7,7a-hexahydro-6-methyl-4H-inden-4-one 、 胍 在 硝酸 作用下， 生成 7-epiptilocaulin nitrate
  参考文献：
  名称：

  Stereoselective synthesis of ptilocaulin and its 7-epimer

  摘要：

  DOI：

  10.1016/s0040-4039(00)84271-9
• 作为产物：
  描述：

  3-碘苄胺 在 镍 、 钯 sodium hypochlorite 、 lithium aluminium tetrahydride 、 氯化亚砜 、 氢气 、 硼酸 、 对甲苯磺酸 、 pyridinium chlorochromate 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 、 水 、 苯 为溶剂， 反应 6.17h， 生成 (5β,6α,7aβ)-5-butyl-1,2,5,6,7,7a-hexahydro-6-methyl-4H-inden-4-one
  参考文献：
  名称：

  Stereoselective synthesis of ptilocaulin and its 7-epimer

  摘要：

  DOI：

  10.1016/s0040-4039(00)84271-9

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.
• Murthy, K. S. Keshava; Hassner, Alfred, Israel Journal of Chemistry, 1991, vol. 31, # 3, p. 239 - 246
  作者：Murthy, K. S. Keshava、Hassner, Alfred

  DOI：——

  日期：——