tert-butyl 3-butyl-6-(3Z-hexenyl)-2-oxocyclohex-3-ene-1-carboxylate | 1079832-54-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: tert-butyl 3-butyl-6-(3Z-hexenyl)-2-oxocyclohex-3-ene-1-carboxylate
• CAS: 1079832-54-4
• 化学式: C₂₁H₃₄O₃
• 分子量: 334.499
• InChiKey: YFXDPPKBACXNNG-NTMALXAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  24.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  tert-butyl 3-butyl-6-(3Z-hexenyl)-2-oxocyclohex-3-ene-1-carboxylate 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以3.20 g的产率得到2-butyl-5-(3Z-hexenyl)-cyclohex-2-en-1-one
  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
• 作为产物：
  描述：

  反-2-,顺-6-壬二烯醛 、 tert-butyl 3-oxooctanoate 在 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 反应 17.5h， 生成 tert-butyl 3-butyl-6-(3Z-hexenyl)-2-oxocyclohex-3-ene-1-carboxylate
  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