(3R,4S,5S)-3-azido-4-benzyloxy-5-fluoroazepane-1-carboxylic acid-tert-butyl ester | 1417557-63-1

• 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: (3R,4S,5S)-3-azido-4-benzyloxy-5-fluoroazepane-1-carboxylic acid-tert-butyl ester
• 英文别名: tert-butyl (3R,4S,5S)-3-azido-5-fluoro-4-phenylmethoxyazepane-1-carboxylate
• CAS: 1417557-63-1
• 化学式: C₁₈H₂₅FN₄O₃
• 分子量: 364.42
• InChiKey: KAGXFRVWBUNGAK-ARFHVFGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  53.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3R,4S,5S)-3-azido-4-benzyloxy-5-fluoroazepane-1-carboxylic acid-tert-butyl ester 在 三氟甲磺酸 、 5%-palladium/activated carbon 、 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 16.0h， 生成 (3R,4S,5S)-3-(4-(benzyloxy)benzamido)-5-fluoro-4-hydroxyazepane-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Divergent response of homologous ATP sites to stereospecific ligand fluorination for selectivity enhancement

  摘要：

  通过立体特异性氟化对同源ATP位点进行复合化学和构象扰动，增强了对同源ATP位点的选择性。

  DOI：

  10.1039/c7ob00129k
• 作为产物：
  描述：

  (2S,3R)-1-allylamino-3-benzyloxy-pent-4-en-2-ol 在 Grubbs catalyst first generation 、 dimethyl sulfide borane 、 叠氮磷酸二苯酯 、 三乙胺 、 三苯基膦 、 [双(2-甲氧基乙基)胺]三氟化硫 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 60.5h， 生成 (3R,4S,5S)-3-azido-4-benzyloxy-5-fluoroazepane-1-carboxylic acid-tert-butyl ester
  参考文献：
  名称：

  Diastereospecific fluorination of substituted azepanes

  摘要：

  Fluorination of bioactive compounds is an important step in drug discovery and development. Fluorination has been extensively studied in acyclic systems, carbocycles, and fused heterocycles. However, there is no report on fluorination of azepanes. As azepanes are components of many biologically active substances and natural products. We herein present the first fluorination examples of substituted azepanes. Fluoroazepanes were prepared by deoxyfluorination diastereospecifically in excellent yields. The absolute configuration at the fluorination site was unambiguously assigned by 2D NMR spectroscopy. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.10.078

文献信息

• Divergent response of homologous ATP sites to stereospecific ligand fluorination for selectivity enhancement
  作者：Alpesh Ramanlal Patel、Ari Hardianto、Shoba Ranganathan、Fei Liu

  DOI：10.1039/c7ob00129k

  日期：——

  Enhanced selectivity for homologous ATP sites by composite chemical and conformational perturbation by stereospecific fluorination.

  通过立体特异性氟化对同源ATP位点进行复合化学和构象扰动，增强了对同源ATP位点的选择性。
• Diastereospecific fluorination of substituted azepanes
  作者：Alpesh Ramanlal Patel、Fei Liu

  DOI：10.1016/j.tet.2012.10.078

  日期：2013.1

  Fluorination of bioactive compounds is an important step in drug discovery and development. Fluorination has been extensively studied in acyclic systems, carbocycles, and fused heterocycles. However, there is no report on fluorination of azepanes. As azepanes are components of many biologically active substances and natural products. We herein present the first fluorination examples of substituted azepanes. Fluoroazepanes were prepared by deoxyfluorination diastereospecifically in excellent yields. The absolute configuration at the fluorination site was unambiguously assigned by 2D NMR spectroscopy. (c) 2012 Elsevier Ltd. All rights reserved.