(4R,5S,6S)-5-hydroxy-4,6-dimethyloctan-3-one | 890933-04-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R,5S,6S)-5-hydroxy-4,6-dimethyloctan-3-one
• CAS: 890933-04-7
• 化学式: C₁₀H₂₀O₂
• 分子量: 172.268
• InChiKey: JDLBYTLZSONDPP-NRPADANISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4R,5S,6S)-5-hydroxy-4,6-dimethyloctan-3-one 在 palladium on activated charcoal 2,6-二甲基吡啶 、 氢气 、 戴斯-马丁氧化剂 、 氟化氢吡啶 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 9.42h， 生成 [(5R,6S,8R,9S,10R,11R)-2-[(2S)-butan-2-yl]-8-[(2R)-1-hydroxypropan-2-yl]-3,5,9,11-tetramethyl-4-oxo-1,7-dioxaspiro[5.5]undec-2-en-10-yl] 3-methylbutanoate
  参考文献：
  名称：

  头孢酮A的全合成

  摘要：

  DOI：

  10.1002/anie.200504573
• 作为产物：
  描述：

  S-(-)-2-甲基-1-丁醇 在 草酰氯 、 四氯化钛 、 二甲基亚砜 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.25h， 生成 (4R,5S,6S)-5-hydroxy-4,6-dimethyloctan-3-one
  参考文献：
  名称：

  立体选择性合成和无环前体形成金耳酮A和B的环化

  摘要：

  头孢吡酮的无环前体是通过立体选择性羟醛策略合成的。该化合物不能进行环化反应形成在Auripyrone A和B中发现的螺缩醛二氢吡喃酮环系统；相反，它通过将C11羟基环化到C15羰基上并随后脱水而形成二氢吡喃环。相反，制备了模型化合物，并显示其环化至螺缩醛二氢吡喃酮环系统和二氢吡喃酮环。

  DOI：

  10.1016/j.tetlet.2006.03.096

文献信息

• Volatiles from the tropical ascomycete <i>Daldinia clavata</i> (Hypoxylaceae, Xylariales)
  作者：Tao Wang、Kathrin I Mohr、Marc Stadler、Jeroen S Dickschat

  DOI：10.3762/bjoc.14.9

  日期：——

  apparatus and analysed by GC-MS. A few compounds were readily identified by comparison of measured to library mass spectra and of retention indices to published data, while for other compounds a synthesis of references was required. For one of the main compounds, 5-hydroxy-4,6-dimethyloctan-3-one, the relative and absolute configuration was determined by synthesis of all eight stereoisomers and gas chromatographic

  通过使用闭环汽提装置收集来自真菌Daldinia clavata的挥发物，并通过GC-MS进行分析。通过比较库质谱图和保留指数与公开数据，可以轻松鉴定出几种化合物，而对于其他化合物，则需要合成参考文献。对于一种主要化合物5-羟基-4,6-二甲基辛-3--3-酮，其相对和绝对构型是通过合成所有八种立体异构体并使用同手性固定相进行气相色谱分析确定的。另一个确定的新天然产物是6-壬基-2H-吡喃-2-酮。还报道了合成挥发物的抗微生物和细胞毒性作用。
• Total Synthesis of Auripyrone A Using a Tandem Non-Aldol Aldol/Paterson Aldol Process as a Key Step
  作者：Michael E. Jung、Ramin Salehi-Rad

  DOI：10.1002/anie.200904607

  日期：2009.11.2

  To aldol or non‐aldol: The titled reaction sequence generates the polypropionate 3 from the epoxy alcohol 1 and the ketone 2 as a single diastereomer. Compound 2 was used for an efficient synthesis of auripyrone A using a highly regioselective hemiketalization of a keto diol and a late‐stage spiroketalization onto a stable hemiketal as the final key steps. TBDPS=tert‐butyldiphenylsilyl, Bz=benzoyl

  To aldol or non-aldol：标题反应序列从环氧醇1和酮2生成聚丙酸酯3作为单一的非对映异构体。化合物2用于有效合成 auripyrone A，使用高度区域选择性的酮二醇半缩酮化和后期螺缩酮化到稳定的半缩酮作为最后的关键步骤。TBDPS=叔丁基二苯基甲硅烷基，Bz=苯甲酰基，TES=三乙基甲硅烷基。
• Total Synthesis of (-)-Ebelactone A and B
  作者：Ian Paterson、Alison N. Hulme

  DOI：10.1021/jo00116a010

  日期：1995.6

  The beta-lactone enzyme inhibitors (-)-ebelactone A (1) and (-)-ebelactone B (2) have been prepared in 12 steps from diethyl ketone (4 and 3% overall yield, respectively). The synthetic strategy adopted for the ebelactones demonstrates the use of reagent- and substrate-derived stereocontrol and requires the minimal use of protecting groups. The stereocenters at C-2, C-3, C-8, C-10, and C-11 were constructed using boron aldol methodology. An asymmetric syn, aldol addition of diethyl ketone to 2-ethyl/acrolein gave adduct 8 in 86% ee, followed by a diastereoselective syn aldol reaction to give 11. Subsequently, an Ireland-Claisen rearrangement was used to relay 1,2-syn into 1,5-syn relative stereochemistry, as in 12 --> 14. In the anti aldol construction of the C-2-C-3 bond, the use of either a propionate or butyrate thioester enolate allowed for a divergent approach from aldehyde 17 to both (-)-ebelactone A and B. Several novel analogues of ebelactone A and B were also prepared with inverted stereochemistry at C-2, C-3, or C-12.
• Total Synthesis of Auripyrone A
  作者：Troy Lister、Michael V. Perkins

  DOI：10.1002/anie.200504573

  日期：2006.4.10
• Stereoselective synthesis and cyclisation of the acyclic precursor to auripyrone A and B
  作者：Michael V. Perkins、Rebecca A. Sampson、John Joannou、Max R. Taylor

  DOI：10.1016/j.tetlet.2006.03.096

  日期：2006.5

  The acyclic precursor to the auripyrones has been synthesized by a stereoselective aldol strategy. This compound fails to undergo cyclisation to form the spiroacetal dihydropyrone ring system found in auripyrone A and B; instead, it forms a dihydropyrone ring by cyclisation of the C11 hydroxyl onto the C15 carbonyl with subsequent dehydration. In contrast, a model compound was prepared and shown to

  头孢吡酮的无环前体是通过立体选择性羟醛策略合成的。该化合物不能进行环化反应形成在Auripyrone A和B中发现的螺缩醛二氢吡喃酮环系统；相反，它通过将C11羟基环化到C15羰基上并随后脱水而形成二氢吡喃环。相反，制备了模型化合物，并显示其环化至螺缩醛二氢吡喃酮环系统和二氢吡喃酮环。