(S)-2,3,4,5,6,7-hexahydro-3-phenyl-5-trifluoromethyl-1,4-oxazepine-7-one | 1149677-56-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧氮杂卓类
• 英文名称: (S)-2,3,4,5,6,7-hexahydro-3-phenyl-5-trifluoromethyl-1,4-oxazepine-7-one
• 英文别名: (3S,5S)-3-phenyl-5-(trifluoromethyl)-1,4-oxazepan-7-one
• CAS: 1149677-56-4
• 化学式: C₁₂H₁₂F₃NO₂
• 分子量: 259.228
• InChiKey: XYAOPXUHPNPAHZ-ZJUUUORDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-2,3,4,5,6,7-hexahydro-3-phenyl-5-trifluoromethyl-1,4-oxazepine-7-one 在 盐酸 、 palladium on activated charcoal 、 氢气 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 16.0h， 以100%的产率得到methyl (S)-4,4,4-trifluoro-3-aminobutyrate hydrochloride
  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：

  (S)-2,3,4,7-tetrahydro-3-phenyl-5-trifluoromethyl-1,4-oxazepine-7-one 在 盐酸 、 sodium cyanoborohydride 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 氯仿 为溶剂， 反应 48.0h， 以68%的产率得到(S)-2,3,4,5,6,7-hexahydro-3-phenyl-5-trifluoromethyl-1,4-oxazepine-7-one
  参考文献：
  名称：

  具有甲基/三氟甲基侧链的基​​于手性β-氨基酸的低分子量有机胶凝剂的合成与评价†

  摘要：

  报道了具有甲基/三氟甲基侧链的基​​于手性β-氨基酸的低分子量有机胶凝剂的合成和胶凝特性。发现侧链的结构和手性是影响胶凝能力的重要参数。三氟甲基化的β-氨基酸的纯对映体由于增强的酰胺氢键的驱动而形成了纤维状网络，因此显示出良好的胶凝特性。对烷基链长度影响的研究表明，更长的烷基链可改善胶凝能力，但在所有分子中均观察到相同的超分子结构，并且在熔点和T g值上均具有奇偶效应。

  DOI：

  10.1039/c8nj05668d

文献信息

• Synthesis and evaluation of chiral β-amino acid-based low-molecular-weight organogelators possessing a methyl/trifluoromethyl side chain
  作者：Koichi Kodama、Ryuta Kawamata、Takuji Hirose

  DOI：10.1039/c8nj05668d

  日期：——

  The synthesis and gelation properties of chiral β-amino acid-based low-molecular-weight organogelators, possessing methyl/trifluoromethyl side chains, are reported. The structure of the side chain and chirality were found to be important parameters affecting the gelation ability. The pure enantiomer of the trifluoromethylated β-amino acid displayed good gelation properties due to the formation of fibrillar

  报道了具有甲基/三氟甲基侧链的基​​于手性β-氨基酸的低分子量有机胶凝剂的合成和胶凝特性。发现侧链的结构和手性是影响胶凝能力的重要参数。三氟甲基化的β-氨基酸的纯对映体由于增强的酰胺氢键的驱动而形成了纤维状网络，因此显示出良好的胶凝特性。对烷基链长度影响的研究表明，更长的烷基链可改善胶凝能力，但在所有分子中均观察到相同的超分子结构，并且在熔点和T g值上均具有奇偶效应。
• 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.