4,4-difluorocyclohexanecarboxylic acid [(1R)-3-oxo-1-phenylpropyl]amide | 1360566-14-8

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代烷
• 英文名称: 4,4-difluorocyclohexanecarboxylic acid [(1R)-3-oxo-1-phenylpropyl]amide
• 英文别名: 4,4-difluoro-N-[(1R)-3-oxo-1-phenylpropyl]cyclohexane-1-carboxamide
• CAS: 1360566-14-8
• 化学式: C₁₆H₁₉F₂NO₂
• 分子量: 295.329
• InChiKey: FCEMFOOGKQYYIR-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  氨甲酸,(甲氧苯基甲基)-,1,1-二甲基乙基酯 在 盐酸 、 水 、 四氯化锡 、 1-羟基苯并三唑 、 对甲苯磺酸 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 49.25h， 生成 4,4-difluorocyclohexanecarboxylic acid [(1R)-3-oxo-1-phenylpropyl]amide
  参考文献：
  名称：

  Access to C-protected β-amino-aldehydes via transacetalization of 6-alcoxy tetrahydrooxazinones and use for pseudo-peptide synthesis

  摘要：

  Efficient access to masked beta-amino-aldehydes was performed starting from 6-alcoxy tetrahydrooxazinone 6a-d (6-ATO). Transacetalization leads to the opening of the cycle to form either unsymmetric acetal 7 or symmetric acetals 16-18. These amino acetals are key compounds, obtained with 99% ee, which can be engaged in efficient peptide coupling. This method could easily provide peptides aldehydes or small amido aldehydes as exemplified with the formal synthesis of ent-Maraviroc. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.01.002

文献信息

• Access to C-protected β-amino-aldehydes via transacetalization of 6-alcoxy tetrahydrooxazinones and use for pseudo-peptide synthesis
  作者：Pavlo Shpak-Kraievskyi、Biaolin Yin、Arnaud Martel、Robert Dhal、Gilles Dujardin、Mathieu Y. Laurent

  DOI：10.1016/j.tet.2012.01.002

  日期：2012.3

  Efficient access to masked beta-amino-aldehydes was performed starting from 6-alcoxy tetrahydrooxazinone 6a-d (6-ATO). Transacetalization leads to the opening of the cycle to form either unsymmetric acetal 7 or symmetric acetals 16-18. These amino acetals are key compounds, obtained with 99% ee, which can be engaged in efficient peptide coupling. This method could easily provide peptides aldehydes or small amido aldehydes as exemplified with the formal synthesis of ent-Maraviroc. (C) 2012 Elsevier Ltd. All rights reserved.