6-oxo-7-epi-cyperone | 339592-15-3

• 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: 6-oxo-7-epi-cyperone
• 英文别名: (2S,4aR)-4a,8-dimethyl-2-prop-1-en-2-yl-3,4,5,6-tetrahydro-2H-naphthalene-1,7-dione
• CAS: 339592-15-3
• 化学式: C₁₅H₂₀O₂
• 分子量: 232.323
• InChiKey: SELCOOAVQBZNHC-XHDPSFHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-oxo-7-epi-cyperone 在 吡啶 、 aluminum oxide 、 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 sodium chlorite 、 sodium tetrahydroborate 、 高氯酸 、 cerium(III) chloride 、 间氯过氧苯甲酸 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 phosphate buffer 、 二氯甲烷 、 水 、 异丙醇 、 乙腈 为溶剂， 反应 154.0h， 生成 (3S,3aR,5aR,9bR)-3-Hydroxy-3,5a,9-trimethyl-3a,5,5a,6,7,9b-hexahydro-3H,4H-naphtho[1,2-b]furan-2,8-dione
  参考文献：
  名称：

  Enantioselective synthesis of (+)-decipienin A

  摘要：

  The enantioselective synthesis of (+)-decipienin A has been carried out. The oxidation of 7-epi-cyperone 2 with molecular oxygen in the presence of methanolic KOH provides de C-6-hydroxylated derivative in quantitative yield. The oxidation of glycols 5a through a Swern oxidation and 14a with TEMPO radical opens up a route to the synthesis of 11-hydroxy sesquiterpenolides. All attempts of oxidation of 5a or 14a with other different oxidation reagents led invariably to fragmentation products. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00048-5
• 作为产物：
  描述：

  7-epi-cyperone 在 aluminum oxide 、 氢氧化钾 、 air 、 pyridinium chlorochromate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 68.0h， 生成 6-oxo-7-epi-cyperone
  参考文献：
  名称：

  Enantioselective synthesis of (+)-decipienin A

  摘要：

  The enantioselective synthesis of (+)-decipienin A has been carried out. The oxidation of 7-epi-cyperone 2 with molecular oxygen in the presence of methanolic KOH provides de C-6-hydroxylated derivative in quantitative yield. The oxidation of glycols 5a through a Swern oxidation and 14a with TEMPO radical opens up a route to the synthesis of 11-hydroxy sesquiterpenolides. All attempts of oxidation of 5a or 14a with other different oxidation reagents led invariably to fragmentation products. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00048-5

文献信息

• CeCl3/NaClO: a safe and efficient reagent for the allylic chlorination of terminal olefins
  作者：F.Javier Moreno-Dorado、Francisco M. Guerra、Francisco L. Manzano、F.Javier Aladro、Zacarı́as D. Jorge、Guillermo M. Massanet

  DOI：10.1016/s0040-4039(03)01630-7

  日期：2003.8

  The preparation of allylic chlorides by reaction of terminal olefins with sodium hypochlorite in the presence of cerium trichloride heptahydrate is described. The scope, limitations and synthetic perspectives of the reaction are discussed.

  描述了通过在三氯化铈七水合物存在下使末端烯烃与次氯酸钠反应来制备烯丙基氯化物。讨论了反应的范围，局限性和合成观点。
• Enantioselective synthesis of (+)-decipienin A
  作者：F.Javier Aladro、Francisco M Guerra、F.Javier Moreno-Dorado、Jesús M Bustamante、Zacarı́as D Jorge、Guillermo M Massanet

  DOI：10.1016/s0040-4020(01)00048-5

  日期：2001.3

  The enantioselective synthesis of (+)-decipienin A has been carried out. The oxidation of 7-epi-cyperone 2 with molecular oxygen in the presence of methanolic KOH provides de C-6-hydroxylated derivative in quantitative yield. The oxidation of glycols 5a through a Swern oxidation and 14a with TEMPO radical opens up a route to the synthesis of 11-hydroxy sesquiterpenolides. All attempts of oxidation of 5a or 14a with other different oxidation reagents led invariably to fragmentation products. (C) 2001 Elsevier Science Ltd. All rights reserved.