(3R,4R,6S)-3-azido-4-benzyloxy-6-fluoroazepane-1-carboxylic acid tert-butyl ester | 1417557-72-2

• 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,4R,6S)-3-azido-4-benzyloxy-6-fluoroazepane-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (3R,4R,6S)-3-azido-6-fluoro-4-phenylmethoxyazepane-1-carboxylate
• CAS: 1417557-72-2
• 化学式: C₁₈H₂₅FN₄O₃
• 分子量: 364.42
• InChiKey: XZAMFZMOHLMYST-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,4R,6S)-3-azido-4-benzyloxy-6-fluoroazepane-1-carboxylic acid tert-butyl ester 在 三氟甲磺酸 、 5%-palladium/activated carbon 、 palladium 10% on activated carbon 、 2-氯-1-甲基吡啶碘化物 、 氢气 、 溶剂黄146 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 34.58h， 生成 2-(4-((((3R,4R,6S)-6-fluoro-3-(4-hydroxybenzamido)azepan-4-yl)oxy)carbonyl)-2,6-dihydroxybenzoyl)-3-hydroxybenzoic acid
  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,4R,6S)-3-azido-4-benzyloxy-6-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

• Conformational regulation of substituted azepanes through selective monofluorination
  作者：Alpesh Ramanlal Patel、Graham Ball、Luke Hunter、Fei Liu

  DOI：10.1039/c3ob40391b

  日期：——

  Substituted azepanes are common bioactive epitopes with flexible ring structures. The conformational effects of monofluorination in model azepane rings were investigated by 1H NMR spectroscopy and computational modelling. A single fluorine atom, installed diastereoselectively, was found to bias the azepane ring to one major conformation for one diastereomer.

  取代的氮杂环庚烷是具有柔性环结构的常见生物活性表位。通过1 H NMR光谱和计算模型研究了单氟在模型氮杂环丙烷环中的构象效应。发现非对映选择性地安装的单个氟原子将氮杂环戊烷环偏向一个非对映异构体的一个主要构象。
• 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.