(2R,5S)-2-((isopropyldimethylsilyl)oxy)-2-methyl-5-(prop-1-en-2-yl)cyclohexanone | 1431302-66-7

• 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: (2R,5S)-2-((isopropyldimethylsilyl)oxy)-2-methyl-5-(prop-1-en-2-yl)cyclohexanone
• 英文别名: (2R,5S)-2-[dimethyl(propan-2-yl)silyl]oxy-2-methyl-5-prop-1-en-2-ylcyclohexan-1-one
• CAS: 1431302-66-7
• 化学式: C₁₅H₂₈O₂Si
• 分子量: 268.472
• InChiKey: OUPDEJCCSLSWCF-DZGCQCFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.32
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R,5S)-2-((isopropyldimethylsilyl)oxy)-2-methyl-5-(prop-1-en-2-yl)cyclohexanone 在 sodium hypochlorite 、 正丁基锂 、 偶氮二异丁腈 、 cerium(III) chloride heptahydrate 、 三(三甲基硅基)硅烷 、 双(三甲基硅烷基)氨基钾 、 sodium iodide 、 copper(ll) bromide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 水 、 丙酮 、 甲苯 、 叔丁醇 、 苯 为溶剂， 反应 8.5h， 生成 (2S,5R,6S)-6-(2-((1S,3S,4R)-3-bromo-4-((isopropyldimethylsilyl)oxy)-4-methylcyclohexyl)allyl)-2-((tert-butyldimethylsilyl)oxy)-2-methyl-5-(prop-1-en-2-yl)cyclohexanone
  参考文献：
  名称：

  Synthesis of the Proposed Structures of Prevezol C

  摘要：

  The first enantioselective synthesis of the proposed relative structures of Prevezol C is reported in 11 linear steps from readily available materials. The unusual syn bromohydrin was installed via a multistep sequence culminating in a diastereoselective geminal dibromide reduction. Discrepancies in the spectral data of the synthetic materials and the natural sample have led to the conclusion that the proposed structures are incorrect

  DOI：

  10.1021/ol400754e
• 作为产物：
  描述：

  (1R,2R,4S)-limonene-1,2-diol 在 2,6-二甲基吡啶 、 2-iodoxybenzoic acid 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 16.0h， 生成 (2R,5S)-2-((isopropyldimethylsilyl)oxy)-2-methyl-5-(prop-1-en-2-yl)cyclohexanone
  参考文献：
  名称：

  Synthesis of the Proposed Structures of Prevezol C

  摘要：

  The first enantioselective synthesis of the proposed relative structures of Prevezol C is reported in 11 linear steps from readily available materials. The unusual syn bromohydrin was installed via a multistep sequence culminating in a diastereoselective geminal dibromide reduction. Discrepancies in the spectral data of the synthetic materials and the natural sample have led to the conclusion that the proposed structures are incorrect

  DOI：

  10.1021/ol400754e

文献信息

• Synthesis of the Proposed Structures of Prevezol C
  作者：Anna E. Leung、Michael Blair、Craig M. Forsyth、Kellie L. Tuck

  DOI：10.1021/ol400754e

  日期：2013.5.3

  The first enantioselective synthesis of the proposed relative structures of Prevezol C is reported in 11 linear steps from readily available materials. The unusual syn bromohydrin was installed via a multistep sequence culminating in a diastereoselective geminal dibromide reduction. Discrepancies in the spectral data of the synthetic materials and the natural sample have led to the conclusion that the proposed structures are incorrect