Acetic acid (1S,2R,4aR)-2-((S)-1,2-dihydroxy-1-methyl-ethyl)-4a,8-dimethyl-7-oxo-1,2,3,4,4a,5,6,7-octahydro-naphthalen-1-yl ester | 339592-09-5

• 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: Acetic acid (1S,2R,4aR)-2-((S)-1,2-dihydroxy-1-methyl-ethyl)-4a,8-dimethyl-7-oxo-1,2,3,4,4a,5,6,7-octahydro-naphthalen-1-yl ester
• 英文别名: Gxintqjqdvyucv-vjunaumwsa-；[(1S,2R,4aR)-2-[(2S)-1,2-dihydroxypropan-2-yl]-4a,8-dimethyl-7-oxo-1,2,3,4,5,6-hexahydronaphthalen-1-yl] acetate
• CAS: 339592-09-5
• 化学式: C₁₇H₂₆O₅
• 分子量: 310.39
• InChiKey: GXINTQJQDVYUCV-VJUNAUMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Acetic acid (1S,2R,4aR)-2-((S)-1,2-dihydroxy-1-methyl-ethyl)-4a,8-dimethyl-7-oxo-1,2,3,4,4a,5,6,7-octahydro-naphthalen-1-yl ester 在 氢氧化钾 、 sodium chlorite 、 sodium dihydrogenphosphate 、 草酰氯 、 氨基磺酸 、 二甲基亚砜 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 24.75h， 生成 (S)-2-Hydroxy-2-((1S,2R,4aR)-1-hydroxy-4a,8-dimethyl-7-oxo-1,2,3,4,4a,5,6,7-octahydro-naphthalen-2-yl)-propionic acid
  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 、 氢氧化钾 、 AD-mix-α 、 air 作用下， 以 甲醇 、 水 、 叔丁醇 为溶剂， 反应 90.0h， 生成 Acetic acid (1S,2R,4aR)-2-((S)-1,2-dihydroxy-1-methyl-ethyl)-4a,8-dimethyl-7-oxo-1,2,3,4,4a,5,6,7-octahydro-naphthalen-1-yl ester
  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.