N,N'-[(1R,2R)-cyclohexane-1,2-diyl]bis[(4S)-4,5-dihydro-2-phenyloxazole-4-carboxamide] | 234443-53-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N,N'-[(1R,2R)-cyclohexane-1,2-diyl]bis[(4S)-4,5-dihydro-2-phenyloxazole-4-carboxamide]
• 英文别名: N,N'-bis-{(4S)-[2-phenyloxazoline]carboxamide}-(1R,2R)-cyclohexane；(4S)-2-phenyl-N-[(1R,2R)-2-[[(4S)-2-phenyl-4,5-dihydro-1,3-oxazole-4-carbonyl]amino]cyclohexyl]-4,5-dihydro-1,3-oxazole-4-carboxamide
• CAS: 234443-53-9
• 化学式: C₂₆H₂₈N₄O₄
• 分子量: 460.533
• InChiKey: OHBCZILQXWXRED-CZYKHXBRSA-N

物化性质

• 沸点：
  779.7±60.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  四氢呋喃 、 三羰基三(丙腈)钼(O) 、 N,N'-[(1R,2R)-cyclohexane-1,2-diyl]bis[(4S)-4,5-dihydro-2-phenyloxazole-4-carboxamide] 以 四氢呋喃 、 甲苯 为溶剂， 生成 (O-6-33)-tricarbonyl(N,N'-[(1R,2R)-cyclohexane-1,2-diyl]bis[(4S)-4,5-dihydro-2-phenyloxazole-4-carboxamide-κN1,κO4])molybdenum(0)*N,N'-[(1R,2R)-cyclohexane-1,2-diyl]bis[(4S)-4,5-dihydro-2-phenyloxazole-4-carboxamide]*0.63tetrahydrofuran
  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
• 作为产物：
  描述：

  苯甲酰胺 在 sodium hydroxide 、 triethyloxonium fluoroborate 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 1-羟基苯并三唑一水物 、 N,N-二异丙基乙胺 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 74.0h， 生成 N,N'-[(1R,2R)-cyclohexane-1,2-diyl]bis[(4S)-4,5-dihydro-2-phenyloxazole-4-carboxamide]
  参考文献：
  名称：

  Enantioselective Molybdenum-Catalyzed Allylic Alkylation Using Chiral Bisoxazoline Ligands

  摘要：

  [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%.

  DOI：

  10.1021/ol990602r

文献信息

• 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.
• 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%.