(1S,2E,4S)-4-acetoxy-1-((2R,5R,6R)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxan-2-yl)-4-phenylbut-2-enyl acetate | 914248-65-0

• 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: (1S,2E,4S)-4-acetoxy-1-((2R,5R,6R)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxan-2-yl)-4-phenylbut-2-enyl acetate
• CAS: 914248-65-0
• 化学式: C₂₂H₃₀O₈
• 分子量: 422.475
• InChiKey: AAIBUZNCQSVVOK-DILIVDLTSA-N

物化性质

• 沸点：
  503.6±50.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.92
• 重原子数：
  30.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  89.52
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (1S,2E,4S)-4-acetoxy-1-((2R,5R,6R)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxan-2-yl)-4-phenylbut-2-enyl acetate 在 potassium osmate(VI) 、 二(氰基苯)二氯化钯 2,6-二甲基吡啶 、 sodium periodate 、 水 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 26.0h， 生成 Acetic acid (1R,2S)-2-acetoxy-1-((2R,5R,6R)-5,6-dimethoxy-5,6-dimethyl-[1,4]dioxan-2-yl)-3-oxo-propyl ester
  参考文献：
  名称：

  1-Phenylprop-2-ynyl Acetate:  A Useful Building Block for the Stereoselective Construction of Polyhydroxylated Chains

  摘要：

  (R)- or (S)-1-phenylprop-2-ynyl acetate was added stereoselectively to aldehydes to afford 4-hydroxy-1-phenylalk-2-ynyl acetates. The transformation of such adducts into the corresponding allylic 1,4-diacetates allowed a highly efficient transfer of chirality from C1 to C3 by a regio- and stereoselective [3,3]-sigmatropic rearrangement. The obtained unsaturated 1,2-diacetates were useful synthetic intermediates whose double bond and/or phenyl group were transformed in different aldehydes, acids, or esters.

  DOI：

  10.1021/ol0616539
• 作为产物：
  描述：

  (+/-)-1-苯基-2-丙炔-1-醇 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 Novozym 435 、 zinc trifluoromethanesulfonate 、 (+)-N-methylephedrine 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 19.5h， 生成 (1S,2E,4S)-4-acetoxy-1-((2R,5R,6R)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxan-2-yl)-4-phenylbut-2-enyl acetate
  参考文献：
  名称：

  1-Phenylprop-2-ynyl Acetate:  A Useful Building Block for the Stereoselective Construction of Polyhydroxylated Chains

  摘要：

  (R)- or (S)-1-phenylprop-2-ynyl acetate was added stereoselectively to aldehydes to afford 4-hydroxy-1-phenylalk-2-ynyl acetates. The transformation of such adducts into the corresponding allylic 1,4-diacetates allowed a highly efficient transfer of chirality from C1 to C3 by a regio- and stereoselective [3,3]-sigmatropic rearrangement. The obtained unsaturated 1,2-diacetates were useful synthetic intermediates whose double bond and/or phenyl group were transformed in different aldehydes, acids, or esters.

  DOI：

  10.1021/ol0616539