(2S,3R,7S,8S)-8-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-3,5,7-trimethyl-decane-4,6-dione | 152428-79-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,3R,7S,8S)-8-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-3,5,7-trimethyl-decane-4,6-dione
• 英文别名: (2S,3R,7S,8S)-2-[tert-butyl(dimethyl)silyl]oxy-3,5,7-trimethyl-8-phenylmethoxydecane-4,6-dione
• CAS: 152428-79-0
• 化学式: C₂₆H₄₄O₄Si
• 分子量: 448.718
• InChiKey: JBJGMRXWACUSSW-JPPJVSBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.44
• 重原子数：
  31
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3R,7S,8S)-8-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-3,5,7-trimethyl-decane-4,6-dione 在 palladium dihydroxide 四丙基高钌酸铵 、 N-甲基吗啉氧化物 、 三氟乙酸 、 环己烯 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 0.5h， 生成 (2S,3R)-2,3-dihydro-6-[(1'R)-1'-methyl-2'-oxobutyl]-2,3,5-trimethyl-4H-pyran-4-one
  参考文献：
  名称：

  High-precision asymmetric synthesis of stegobiol and stegobinone via boronic esters

  摘要：

  Highly stereoselective boronic ester chemistry has been used to synthesize the drugstore beetle pheromones stegobiol and stegobinone. The convergent route utilizes a single intermediate containing all of the stereogenic centers for both segments of the pheromones, requires only one chromatographic separation, and is the first synthesis to provide pure, crystalline samples.

  DOI：

  10.1021/jo00076a006
• 作为产物：
  描述：

  (4R,5S)-5-t-butyldimethylsilyloxy-4-methylhexan-3-one 在 重铬酸吡啶 、 molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 (2S,3R,7S,8S)-8-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-3,5,7-trimethyl-decane-4,6-dione
  参考文献：
  名称：

  High-precision asymmetric synthesis of stegobiol and stegobinone via boronic esters

  摘要：

  Highly stereoselective boronic ester chemistry has been used to synthesize the drugstore beetle pheromones stegobiol and stegobinone. The convergent route utilizes a single intermediate containing all of the stereogenic centers for both segments of the pheromones, requires only one chromatographic separation, and is the first synthesis to provide pure, crystalline samples.

  DOI：

  10.1021/jo00076a006

文献信息

• High-precision asymmetric synthesis of stegobiol and stegobinone via boronic esters
  作者：Donald S. Matteson、Hon Wah Man

  DOI：10.1021/jo00076a006

  日期：1993.11

  Highly stereoselective boronic ester chemistry has been used to synthesize the drugstore beetle pheromones stegobiol and stegobinone. The convergent route utilizes a single intermediate containing all of the stereogenic centers for both segments of the pheromones, requires only one chromatographic separation, and is the first synthesis to provide pure, crystalline samples.