(1S,2S,4R)-3-[1-((1S,2R,5S)-2-Isopropyl-5-methyl-cyclohexyloxycarbonyl)-meth-(Z)-ylidene]-bicyclo[2.2.1]heptane-2-carboxylic acid (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester | 175418-22-1

• 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: (1S,2S,4R)-3-[1-((1S,2R,5S)-2-Isopropyl-5-methyl-cyclohexyloxycarbonyl)-meth-(Z)-ylidene]-bicyclo[2.2.1]heptane-2-carboxylic acid (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester
• CAS: 175418-22-1
• 化学式: C₃₀H₄₈O₄
• 分子量: 472.709
• InChiKey: CXLMPYCHDRRLCX-PULUXLTPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.97
• 重原子数：
  34.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1S,2S,4R)-3-[1-((1S,2R,5S)-2-Isopropyl-5-methyl-cyclohexyloxycarbonyl)-meth-(Z)-ylidene]-bicyclo[2.2.1]heptane-2-carboxylic acid (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester 在 臭氧 作用下， 以 二氯甲烷 为溶剂， 以98%的产率得到(1S,2S,4R)-3-Oxo-bicyclo[2.2.1]heptane-2-carboxylic acid (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester
  参考文献：
  名称：

  Structure and Asymmetric Diels−Alder Reactions of Optically Active Allene-1,3-dicarboxylates

  摘要：

  Optically active allene-1,3-dicarboxylates (1a and 2a), which contain the axial asymmetry of the allene moiety, were prepared. The Diels-Alder reaction of 1a and 2a with cyclopentadiene afforded the 1:1 (1a or 2a to cyclopentadiene) endo adducts 3a and 4a through the combination of the sterically favorable approach of the diene and the dienophile owing to the axial asymmetry of the allene moiety and the effective secondary orbital interaction. The absolute configurations of 3a and 4a were determined by chemical transformation and X-ray analysis. The absolute configuration of the axial asymmetry of la was also determined to be R by X-ray analysis.

  DOI：

  10.1021/jo951762t
• 作为产物：
  描述：

  (1R,2S,4S)-3-[1-((1S,2R,5S)-2-Isopropyl-5-methyl-cyclohexyloxycarbonyl)-meth-(Z)-ylidene]-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 以98%的产率得到(1S,2S,4R)-3-[1-((1S,2R,5S)-2-Isopropyl-5-methyl-cyclohexyloxycarbonyl)-meth-(Z)-ylidene]-bicyclo[2.2.1]heptane-2-carboxylic acid (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester
  参考文献：
  名称：

  Structure and Asymmetric Diels−Alder Reactions of Optically Active Allene-1,3-dicarboxylates

  摘要：

  Optically active allene-1,3-dicarboxylates (1a and 2a), which contain the axial asymmetry of the allene moiety, were prepared. The Diels-Alder reaction of 1a and 2a with cyclopentadiene afforded the 1:1 (1a or 2a to cyclopentadiene) endo adducts 3a and 4a through the combination of the sterically favorable approach of the diene and the dienophile owing to the axial asymmetry of the allene moiety and the effective secondary orbital interaction. The absolute configurations of 3a and 4a were determined by chemical transformation and X-ray analysis. The absolute configuration of the axial asymmetry of la was also determined to be R by X-ray analysis.

  DOI：

  10.1021/jo951762t