(2R,3R,4R)-3-Methoxy-2,4-dimethyl-6-oxo-hexanoic acid methyl ester | 401911-94-2

• 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: (2R,3R,4R)-3-Methoxy-2,4-dimethyl-6-oxo-hexanoic acid methyl ester
• CAS: 401911-94-2
• 化学式: C₁₀H₁₈O₄
• 分子量: 202.251
• InChiKey: QASFANQECADNCK-IWSPIJDZSA-N

物化性质

• 沸点：
  278.8±30.0 °C(Predicted)
• 密度：
  1.001±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.04
• 重原子数：
  14.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  (2R,3R,4R)-3-Methoxy-2,4-dimethyl-6-oxo-hexanoic acid methyl ester 在 咪唑 、 lithium tri-t-butoxyaluminum hydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Oxabicyclo[3.2.1]octenes in Organic Synthesis:  Direct Ring Opening of Oxabicyclo[3.2.1] Ring Systems with Diisobutylaluminum Hydride and a Silyl Ketene AcetalSynthesis of the Chiral C(19)−C(26) and C(27)−C(32) Fragments of Scytophycin C

  摘要：

  GRAPHICSAn efficient strategy for transforming meso-oxabicyclo[3.2.1]octenone 1 into optically active intermediates for macrolide synthesis has been developed. The direct bridgehead opening of optically active oxabicyclo[3.2.1]octene derivative 2 with hydride or a silyl ketene acetal utilizing the highly polar medium lithium perchlorate in diethyl ether resulted in highly functionalized cycloheptenones, which were transformed into the C(19)-C(26) and C(27)-C(32) fragments of Scytophycin C.

  DOI：

  10.1021/ol010253c
• 作为产物：
  描述：

  (1R,2S,4R,5S)-2,4-dimethyl-8-oxa-bicyclo[3.2.1]oct-6-en-3-one 在 lead(IV) acetate 、 四氧化锇 、 lithium aluminium tetrahydride 、 N-甲基吲哚酮 、 2,6-二叔丁基吡啶 、 四丙基高钌酸铵 、 lithium [R(R*,R*)]-(+)-bis(α-methylbenzyl)amide 、 叔丁基二甲基氯硅烷 、 lithium tri-t-butoxyaluminum hydride 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 乙醚 、 苯 为溶剂， 反应 28.0h， 生成 (2R,3R,4R)-3-Methoxy-2,4-dimethyl-6-oxo-hexanoic acid methyl ester
  参考文献：
  名称：

  Oxabicyclo[3.2.1]octenes in Organic Synthesis:  Direct Ring Opening of Oxabicyclo[3.2.1] Ring Systems with Diisobutylaluminum Hydride and a Silyl Ketene AcetalSynthesis of the Chiral C(19)−C(26) and C(27)−C(32) Fragments of Scytophycin C

  摘要：

  GRAPHICSAn efficient strategy for transforming meso-oxabicyclo[3.2.1]octenone 1 into optically active intermediates for macrolide synthesis has been developed. The direct bridgehead opening of optically active oxabicyclo[3.2.1]octene derivative 2 with hydride or a silyl ketene acetal utilizing the highly polar medium lithium perchlorate in diethyl ether resulted in highly functionalized cycloheptenones, which were transformed into the C(19)-C(26) and C(27)-C(32) fragments of Scytophycin C.

  DOI：

  10.1021/ol010253c