ethyl 4-amino-3-decyloxybenzoate | 1206552-89-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 4-amino-3-decyloxybenzoate
• 英文别名: Ethyl 4-amino-3-decoxybenzoate；ethyl 4-amino-3-decoxybenzoate
• CAS: 1206552-89-7
• 化学式: C₁₉H₃₁NO₃
• 分子量: 321.46
• InChiKey: BNQGWOXZAFKGBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  23
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 4-amino-3-decyloxybenzoate 、 4-甲氧基苯甲醛 在 苯磺酸 、 吡啶硼烷 作用下， 以 乙醇 、 甲醇 为溶剂， 反应 15.0h， 以62%的产率得到ethyl 4-(4-methoxybenzylamino)-3-decyloxybenzoate
  参考文献：
  名称：

  Synthesis and chiral discrimination of cyclic aromatic amides and the determination of their absolute configuration by TD-DFT calculations

  摘要：

  Novel chiral cyclic molecules composed of aromatic triamides were constructed in modest yield from 4-N-(4'-methoxybenzyl)amino-3-decyloxybenzoic acid using dichlorotriphenylphosphorane, because of the preorganized component of the tertiary benzanilide moieties. A racemic mixture of two diastereomers, syn and anti conformers of cyclic aromatic triamides, was resolved into enantiomers by HPLC using a preparative chiral column. The absolute configuration of each enantiomer in both diastereomers was determined by comparison of the time-dependent density functional theory (TD-DFT) calculated circular dichroic (CD) spectra with the experimentally derived CD spectra recorded on each sample. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.10.032
• 作为产物：
  描述：

  ethyl 3-decyloxy-4-nitrobenzoate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 30.0h， 以91%的产率得到ethyl 4-amino-3-decyloxybenzoate
  参考文献：
  名称：

  Synthesis and chiral discrimination of cyclic aromatic amides and the determination of their absolute configuration by TD-DFT calculations

  摘要：

  Novel chiral cyclic molecules composed of aromatic triamides were constructed in modest yield from 4-N-(4'-methoxybenzyl)amino-3-decyloxybenzoic acid using dichlorotriphenylphosphorane, because of the preorganized component of the tertiary benzanilide moieties. A racemic mixture of two diastereomers, syn and anti conformers of cyclic aromatic triamides, was resolved into enantiomers by HPLC using a preparative chiral column. The absolute configuration of each enantiomer in both diastereomers was determined by comparison of the time-dependent density functional theory (TD-DFT) calculated circular dichroic (CD) spectra with the experimentally derived CD spectra recorded on each sample. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.10.032

文献信息

• Synthesis and chiral discrimination of cyclic aromatic amides and the determination of their absolute configuration by TD-DFT calculations
  作者：Kosuke Katagiri、Takashi Ikeda、Atsuya Muranaka、Masanobu Uchiyama、Masahide Tominaga、Isao Azumaya

  DOI：10.1016/j.tetasy.2009.10.032

  日期：2009.11

  Novel chiral cyclic molecules composed of aromatic triamides were constructed in modest yield from 4-N-(4'-methoxybenzyl)amino-3-decyloxybenzoic acid using dichlorotriphenylphosphorane, because of the preorganized component of the tertiary benzanilide moieties. A racemic mixture of two diastereomers, syn and anti conformers of cyclic aromatic triamides, was resolved into enantiomers by HPLC using a preparative chiral column. The absolute configuration of each enantiomer in both diastereomers was determined by comparison of the time-dependent density functional theory (TD-DFT) calculated circular dichroic (CD) spectra with the experimentally derived CD spectra recorded on each sample. (C) 2009 Elsevier Ltd. All rights reserved.