(2S,3R)-3-methoxy-6-phenylhexane-1,2-diol | 1400695-37-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2S,3R)-3-methoxy-6-phenylhexane-1,2-diol
• CAS: 1400695-37-5
• 化学式: C₁₃H₂₀O₃
• 分子量: 224.3
• InChiKey: CVSXLQRJEUNYKA-QWHCGFSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3R)-3-methoxy-6-phenylhexane-1,2-diol 在 2,2,6,6-四甲基哌啶氧化物 、 sodium hypochlorite 、 sodium chlorite 作用下， 以 aq. phosphate buffer 、 甲苯 为溶剂， 反应 1.5h， 以94%的产率得到(2R,3R)-2-hydroxy-3-methoxy-6-phenylhexanoic acid
  参考文献：
  名称：

  Chemoselective Catalytic Oxidation of 1,2-Diols to α-Hydroxy Acids Controlled by TEMPO–ClO₂ Charge-Transfer Complex

  摘要：

  Chemoselective catalytic oxidation from 1,2-diols to a-hydroxy acids in a cat. TEMPO/cat. NaOCl/NaClO2 system has been achieved. The use of a two-phase condition consisting of hydrophobic toluene and water suppresses the concomitant oxidative cleavage. A study of the mechanism suggests that the observed selectivity is derived from the precise solubility: control of diols and hydroxy acids as well as the active species Of TEMPO, Although the oxoammonium species TEMPO+Cl- is hydrophilic, the active species dissolves into the organic layer by the formation of the charge-transfer (CT) complex TEMPO-ClO2 under the reaction conditions.

  DOI：

  10.1021/acs.orglett.5b01003
• 作为产物：
  描述：

  甲醇 、 [(2S,3S)-3-(3-phenylpropyl)oxiran-2-yl]methanol 在 europium(III) trifluoromethanesulfonate 作用下， 以86%的产率得到(2S,3R)-3-methoxy-6-phenylhexane-1,2-diol
  参考文献：
  名称：

  Organocatalytic One-Pot Oxidative Cleavage of Terminal Diols to Dehomologated Carboxylic Acids

  摘要：

  The organocatalytic one-pot oxidative cleavage of terminal 1,2-diols to one-carbon-unit-shorter carboxylic acids is described. The combination of 1-Me-AZADO (cat.), NaOCl (cat.), and NaClO2 caused smooth one-pot oxidative cleavage under mild conditions. A broad range of substrates including carbohydrates and N-protected amino diols were converted without epimerization. Terminal triols and tetraols respectively underwent cleavage of their C-2 and C-3 moieties to afford their corresponding two- and three-carbon-unit-shorter carboxylic acids.

  DOI：

  10.1021/ol3021429