ethyl (4S)-4,5-dihydro-4-(1-methylethyl)oxazole-2-carboxylate | 234443-57-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: ethyl (4S)-4,5-dihydro-4-(1-methylethyl)oxazole-2-carboxylate
• 英文别名: (S)-(-)-4-iso-propyloxazoline-2-carboxylic acid ethyl ester；(S)-ethyl 4-isopropyl-4,5-dihydrooxazole-2-carboxylate；ethyl (4S)-4-propan-2-yl-4,5-dihydro-1,3-oxazole-2-carboxylate
• CAS: 234443-57-3
• 化学式: C₉H₁₅NO₃
• 分子量: 185.223
• InChiKey: VARYVCQGPOMZKW-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  47.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,2S)-(+)-1,2-环己二胺 、 ethyl (4S)-4,5-dihydro-4-(1-methylethyl)oxazole-2-carboxylate 在 sodium hydride 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以22%的产率得到N,N'-[(1S,2S)-cyclohexane-1,2-diyl]bis[(4S)-4,5-dihydro-4-(1-methylethyl)oxazole-2-carboxamide]
  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：

  L-缬氨醇 、 草酸酰胺乙酯 在 triethyloxonium fluoroborate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 48.0h， 以70%的产率得到ethyl (4S)-4,5-dihydro-4-(1-methylethyl)oxazole-2-carboxylate
  参考文献：
  名称：

  钯催化未活化的γ-亚甲基C（sp3）的芳基化作用？H和δ-C ？含恶唑啉-羧酸盐助剂的H键

  摘要：

  未活化的γ的钯-催化的芳基化-亚甲基C（SP 3） H和远程δ-C  H键通过使用恶唑啉甲酸甲酯定向基团已被开发。在广泛的底物范围和对官能团（即卤素，硝基，氰基，醚，三氟甲基，胺和酯）的高耐受性下发生丙烯酸化。可以在酸性条件下除去恶唑啉型助剂。

  DOI：

  10.1002/chem.201502621

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%.
• Palladium-Catalyzed Arylation of Unactivated γ-Methylene C(sp³)H and δ-CH Bonds with an Oxazoline-Carboxylate Auxiliary
  作者：Peng-Xiang Ling、Sheng-Long Fang、Xue-Song Yin、Kai Chen、Bo-Zheng Sun、Bing-Feng Shi

  DOI：10.1002/chem.201502621

  日期：2015.11.23

  A palladium‐catalyzed arylation of unactivated γ‐methylene C(sp3)H and remote δ‐CH bonds by using an oxazoline‐carboxylate directing group has been developed. Arylation occurs with a broad substrate scope and high tolerance of functional groups (i.e., halogen, nitro, cyano, ether, trifluoromethyl, amine, and ester). The oxazoline‐type auxiliary can be removed under acidic conditions.

  未活化的γ的钯-催化的芳基化-亚甲基C（SP 3） H和远程δ-C  H键通过使用恶唑啉甲酸甲酯定向基团已被开发。在广泛的底物范围和对官能团（即卤素，硝基，氰基，醚，三氟甲基，胺和酯）的高耐受性下发生丙烯酸化。可以在酸性条件下除去恶唑啉型助剂。