dimethyl 2-methyl-2-[(E)-3-phenoxyprop-2-enyl]propanedioate

• 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: dimethyl 2-methyl-2-[(E)-3-phenoxyprop-2-enyl]propanedioate
• 英文别名: E-2-methyl-2-(3-phenoxy-allyl)malonic acid dimethyl ester
• 化学式: C₁₅H₁₈O₅
• 分子量: 278.305
• InChiKey: OVUDSJAFNSSEDG-YRNVUSSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (E)-3-phenoxyprop-2-en-1-ol 在 三羰基三(丙腈)钼(O) 4-二甲氨基吡啶 、 [(1S,2S)-cyclohexane-1,2-diyl] chiral dihydrooxazole ligand 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 108.0h， 生成 dimethyl 2-methyl-2-[(E)-3-phenoxyprop-2-enyl]propanedioate
  参考文献：
  名称：

  Highly Enantio- and Regioselective Allylic Alkylations Catalyzed by Chiral [Bis(dihydrooxazole)]molybdenum Complexes

  摘要：

  A series of chiral C-2-symmetric bis[dihydrooxazoles] with a trans-1,2-diaminocyclohexane backbone was synthesized. In view of the promising results obtained by Trost et al with related bis[pyridine] ligands, we tested these new ligands in the enantioselective molybdenum-catalyzed allylic alkylation of 1- and 3-monosubstituted allylic substrates. Enantiomer excesses of up to 98% and branched/linear ratios of up to 11 : 1 were obtained with (E)-3-(alkyl)allyl carbonates. (E)-3-Phenoxyallyl acetate gave a branclied/linear ratio of > 20:1 and an ee of 98%. Crystal structures of the free ligand 7a and of its tricarbonylmolybdenum(0) complex 28 are reported.

  DOI：

  10.1002/1522-2675(20011017)84:10<3178::aid-hlca3178>3.0.co;2-q

文献信息

• Enantioselective Molybdenum-Catalyzed Allylic Alkylation Using Chiral Bisoxazoline Ligands
  作者：Frank Glorius、Andreas Pfaltz

  DOI：10.1021/ol990602r

  日期：1999.7.1

  [GRAPHICS]A series of chiral C-2-symmetric bisoxazolines with trans-1,2-diaminocyclohexane backbones was synthesized. In View of the promising results obtained by Trost with analogous bispyridine ligands, we tested our new ligands in the enantioselective molybdenum-catalyzed allylic alkylation of 1- and 3-monosubstituted allylic substrates, Enantiomeric excesses of up to 98% and branched/linear ratios of up to 11:1 were obtained with (E)-3-(n-alkyl)allyl carbonates. (E)-3-Phenoxyallyl acetate gave a branched/linear ratio of >20:1 and an ee of 98%.
• Highly Enantio- and Regioselective Allylic Alkylations Catalyzed by Chiral [Bis(dihydrooxazole)]molybdenum Complexes
  作者：Frank Glorius、Markus Neuburger、Andreas Pfaltz

  DOI：10.1002/1522-2675(20011017)84:10<3178::aid-hlca3178>3.0.co;2-q

  日期：2001.10.17

  A series of chiral C-2-symmetric bis[dihydrooxazoles] with a trans-1,2-diaminocyclohexane backbone was synthesized. In view of the promising results obtained by Trost et al with related bis[pyridine] ligands, we tested these new ligands in the enantioselective molybdenum-catalyzed allylic alkylation of 1- and 3-monosubstituted allylic substrates. Enantiomer excesses of up to 98% and branched/linear ratios of up to 11 : 1 were obtained with (E)-3-(alkyl)allyl carbonates. (E)-3-Phenoxyallyl acetate gave a branclied/linear ratio of > 20:1 and an ee of 98%. Crystal structures of the free ligand 7a and of its tricarbonylmolybdenum(0) complex 28 are reported.