methyl 2-[(4S)-4-phenyl-2-(trifluoromethyl)-1,3-oxazolidin-2-yl]acetate | 1149677-52-0

• 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: methyl 2-[(4S)-4-phenyl-2-(trifluoromethyl)-1,3-oxazolidin-2-yl]acetate
• CAS: 1149677-52-0
• 化学式: C₁₃H₁₄F₃NO₃
• 分子量: 289.254
• InChiKey: ZTKPVVLWTQUTHE-RWANSRKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2-[(4S)-4-phenyl-2-(trifluoromethyl)-1,3-oxazolidin-2-yl]acetate 在 溴化锡 作用下， 以 邻二甲苯 为溶剂， 反应 4.0h， 以75%的产率得到(S)-2,3,4,7-tetrahydro-3-phenyl-5-trifluoromethyl-1,4-oxazepine-7-one
  参考文献：
  名称：

  A practical method to access enantiopure β-perfluoroalkyl-β-amino acids: diastereoselective reduction of cyclic enamino-esters

  摘要：

  A highly practical method to access enantiopure beta-perfluoroalkyl-beta-amino acids was developed, which Could be conducted Without any expensive reagent, special apparatus/technique, nor tedious chromatographic separation. The condensation of methyl 4,4,4-trifluoro-3-oxobutanoate with (S)-2-amino-2-phenylethanol, followed by an intramoleculer transesterification, gave an enamino-ester with a seven-membered ring structure. The hydride reduction of the cyclic enamino-ester proceeded with excellent diastereoselectivity (dr = 95:5-97:3) to give the corresponding cyclic amino-ester. The major isomer of the cyclic amino-ester was readily separated from the minor one and successfully converted into (S)-3-amino-4,4,4-trifluorobutanoic acid (five steps, 38% overall yield, >99% ee). Concerning the key step of this synthesis, the same strategy was applicable to another substrate: the asymmetric hydride reduction of a cyclic enamino-ester with a pentafluoroethyl group also proceeded in excellent diastereoselectivity (dr = 96:4). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.01.159
• 作为产物：
  描述：

  三氟乙酰乙酸甲酯 、 L-苯甘氨醇 在 溶剂黄146 作用下， 以 氯仿 为溶剂， 反应 12.0h， 以81%的产率得到methyl 2-[(4S)-4-phenyl-2-(trifluoromethyl)-1,3-oxazolidin-2-yl]acetate
  参考文献：
  名称：

  A practical method to access enantiopure β-perfluoroalkyl-β-amino acids: diastereoselective reduction of cyclic enamino-esters

  摘要：

  A highly practical method to access enantiopure beta-perfluoroalkyl-beta-amino acids was developed, which Could be conducted Without any expensive reagent, special apparatus/technique, nor tedious chromatographic separation. The condensation of methyl 4,4,4-trifluoro-3-oxobutanoate with (S)-2-amino-2-phenylethanol, followed by an intramoleculer transesterification, gave an enamino-ester with a seven-membered ring structure. The hydride reduction of the cyclic enamino-ester proceeded with excellent diastereoselectivity (dr = 95:5-97:3) to give the corresponding cyclic amino-ester. The major isomer of the cyclic amino-ester was readily separated from the minor one and successfully converted into (S)-3-amino-4,4,4-trifluorobutanoic acid (five steps, 38% overall yield, >99% ee). Concerning the key step of this synthesis, the same strategy was applicable to another substrate: the asymmetric hydride reduction of a cyclic enamino-ester with a pentafluoroethyl group also proceeded in excellent diastereoselectivity (dr = 96:4). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.01.159

文献信息

• A practical method to access enantiopure β-perfluoroalkyl-β-amino acids: diastereoselective reduction of cyclic enamino-esters
  作者：Yasuhiro Ishida、Nobutaka Iwahashi、Nao Nishizono、Kazuhiko Saigo

  DOI：10.1016/j.tetlet.2009.01.159

  日期：2009.4

  A highly practical method to access enantiopure beta-perfluoroalkyl-beta-amino acids was developed, which Could be conducted Without any expensive reagent, special apparatus/technique, nor tedious chromatographic separation. The condensation of methyl 4,4,4-trifluoro-3-oxobutanoate with (S)-2-amino-2-phenylethanol, followed by an intramoleculer transesterification, gave an enamino-ester with a seven-membered ring structure. The hydride reduction of the cyclic enamino-ester proceeded with excellent diastereoselectivity (dr = 95:5-97:3) to give the corresponding cyclic amino-ester. The major isomer of the cyclic amino-ester was readily separated from the minor one and successfully converted into (S)-3-amino-4,4,4-trifluorobutanoic acid (five steps, 38% overall yield, >99% ee). Concerning the key step of this synthesis, the same strategy was applicable to another substrate: the asymmetric hydride reduction of a cyclic enamino-ester with a pentafluoroethyl group also proceeded in excellent diastereoselectivity (dr = 96:4). (C) 2009 Elsevier Ltd. All rights reserved.