(1S,2S)-1-(((4-methoxybenzoyl)oxy)methyl)-4,4-dimethoxy-1,2-cyclohexanediol | 161578-83-2

• 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: (1S,2S)-1-(((4-methoxybenzoyl)oxy)methyl)-4,4-dimethoxy-1,2-cyclohexanediol
• 英文别名: [(1S,2S)-1,2-dihydroxy-4,4-dimethoxycyclohexyl]methyl 4-methoxybenzoate
• CAS: 161578-83-2
• 化学式: C₁₇H₂₄O₇
• 分子量: 340.373
• InChiKey: ZJDHUSVAKZVYFM-HOCLYGCPSA-N

物化性质

• 沸点：
  461.7±45.0 °C(predicted)
• 密度：
  1.26±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  94.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1S,2S)-1-(((4-methoxybenzoyl)oxy)methyl)-4,4-dimethoxy-1,2-cyclohexanediol 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 生成 4-Methoxy-benzoic acid (S)-1-hydroxy-4,4-dimethoxy-2-oxo-cyclohexylmethyl ester
  参考文献：
  名称：

  Short Enantioselective Synthesis of (-)-Ovalicin, a Potent Inhibitor of Angiogenesis, Using Substrate-Enhanced Catalytic Asymmetric Dihydroxylation

  摘要：

  DOI：

  10.1021/ja00105a084
• 作为产物：
  描述：

  对甲氧基苯甲酰氯 在 4-二甲氨基吡啶 、 potassium osmate(VI) 、 Hydroquinone 1,4-phthalazinediyl diether 、 甲基磺酰胺 、 potassium carbonate 、 三乙胺 、 potassium hexacyanoferrate(III) 作用下， 以 二氯甲烷 、 叔丁醇 为溶剂， 反应 9.0h， 生成 (1S,2S)-1-(((4-methoxybenzoyl)oxy)methyl)-4,4-dimethoxy-1,2-cyclohexanediol
  参考文献：
  名称：

  The application of a mechanistic model leads to the extension of the Sharpless asymmetric dihydroxylation to allylic 4-methoxybenzoates and conformationally related amine and homoallylic alcohol derivatives.

  摘要：

  The scope and utility of the Sharpless asymmetric dihydroxylation has been expanded to include the use of allylic 4-methoxybenzoates as precursors of a wide variety of substituted chiral glycerol derivatives. The allylic 4-methoxybenzoyl group was found to be superior to other allylic alcohol protecting groups with respect to both yield and enantiomeric purity of the product. For example, asymmetric dihydroxylation of allyl 4-methoxybenzoate (6a) using the (DHQD)(2)PYDZ . OsO4 (1 . OsO4) catalyst system affords (S)-3-(4-methoxybenzoyloxy)-1,2-propanediol (7a) in >99% yield and 98% ee. The 4-methoxybenzoates of a variety of other allylic alcohols also serve as excellent substrates, in contrast to the parent alcohols themselves. The efficient asymmetric dihydroxylation of homoallylic 4-methoxyphenyl ethers (12a and 15), allyl 9-fluorenimine (18b), bis(homoallyl) 4-methoxybenzoate (14) and other structurally related substrates is also described. This methodology was developed under mechanistic guidance from the transition state model advanced earlier by us for the bis-cinchona alkaloid catalyzed asymmetric dihydroxylation reaction. The 4-methoxybenzoyl group functions not only to selectively protect one of the hydroxy groups of the product triol for subsequent synthetic manipulation but also to provide an extended binding group that participates in hydrophobic and aryl-aryl interactions with the U-shaped binding pocket of the (DHQD)(2)PYDZ . OsO4 catalyst (1 . OsO4), thereby enhancing enantioselectivity.

  DOI：

  10.1021/ja00149a003