(4aR,7R,8R)-7-((S)-1,2-Dihydroxy-1-methyl-ethyl)-8-hydroxy-1,4a-dimethyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one | 339592-20-0

• 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: (4aR,7R,8R)-7-((S)-1,2-Dihydroxy-1-methyl-ethyl)-8-hydroxy-1,4a-dimethyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one
• 英文别名: Xapfamtvkgomle-judxgummsa-；(4aR,7R,8R)-7-[(2S)-1,2-dihydroxypropan-2-yl]-8-hydroxy-1,4a-dimethyl-3,4,5,6,7,8-hexahydronaphthalen-2-one
• CAS: 339592-20-0
• 化学式: C₁₅H₂₄O₄
• 分子量: 268.353
• InChiKey: XAPFAMTVKGOMLE-JUDXGUMMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4aR,7R,8R)-7-((S)-1,2-Dihydroxy-1-methyl-ethyl)-8-hydroxy-1,4a-dimethyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 sodium chlorite 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 、 phosphate buffer 、 水 、 乙腈 为溶剂， 反应 120.0h， 生成 6β,10α-α-santonin
  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 吡啶 、 aluminum oxide 、 氢氧化钾 、 sodium tetrahydroborate 、 高氯酸 、 cerium(III) chloride 、 air 、 间氯过氧苯甲酸 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 异丙醇 为溶剂， 反应 126.0h， 生成 (4aR,7R,8R)-7-((S)-1,2-Dihydroxy-1-methyl-ethyl)-8-hydroxy-1,4a-dimethyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one
  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

• 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.