(2S,7S)-7-(4-fluorophenoxymethyl)-2-[N,O-bis(phenoxycarbonyl)-3-butyn-4-yl]oxepane | 850453-95-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2S,7S)-7-(4-fluorophenoxymethyl)-2-[N,O-bis(phenoxycarbonyl)-3-butyn-4-yl]oxepane
• 英文别名: [4-[(2S,7S)-7-[(4-fluorophenoxy)methyl]oxepan-2-yl]but-3-ynyl-phenoxycarbonylamino] phenyl carbonate
• CAS: 850453-95-1
• 化学式: C₃₁H₃₀FNO₇
• 分子量: 547.58
• InChiKey: NQYDHSQMRKSNSN-WNJJXGMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  40
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  83.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2S,7S)-7-(4-fluorophenoxymethyl)-2-[N,O-bis(phenoxycarbonyl)-3-butyn-4-yl]oxepane 在 氨 作用下， 以 甲醇 为溶剂， 以65%的产率得到(2S,7S)-2-(4-fluorophenoxymethyl)-7-(1-N-hydroxyureidyl-3-butyn-4-yl)oxepane
  参考文献：
  名称：

  Stereoselective synthesis of (2S,7S)-7-(4-phenoxymethyl)-2-(1-N-hydroxyureidyl-3-butyn-4-yl)oxepane: a potential anti-asthmatic drug candidate

  摘要：

  We have achieved a short, efficient stereoselective synthesis of 7-membered oxepane derivatives with potential against asthma. Highlights of our synthetic strategy are regioselective oxidation of a hydroxyl group and efficient ring closure of an open chain aldehyde to a 2-benzenesulfonyl oxepane derivative with PhSO2H. Surprisingly the cis-isomer showed better activity than the traps-isomer. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.01.024
• 作为产物：
  描述：

  (S)-2-((4-氟苯氧基)甲基)环氧乙烷 在 palladium on activated charcoal 2-碘酰苯甲酸 、 氢气 、 异丙基溴化镁 、 对甲苯磺酸 、 magnesium 、 1,2-二溴乙烷 、 三苯基膦 、 calcium chloride 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 25.25h， 生成 (2S,7S)-7-(4-fluorophenoxymethyl)-2-[N,O-bis(phenoxycarbonyl)-3-butyn-4-yl]oxepane
  参考文献：
  名称：

  Stereoselective synthesis of (2S,7S)-7-(4-phenoxymethyl)-2-(1-N-hydroxyureidyl-3-butyn-4-yl)oxepane: a potential anti-asthmatic drug candidate

  摘要：

  We have achieved a short, efficient stereoselective synthesis of 7-membered oxepane derivatives with potential against asthma. Highlights of our synthetic strategy are regioselective oxidation of a hydroxyl group and efficient ring closure of an open chain aldehyde to a 2-benzenesulfonyl oxepane derivative with PhSO2H. Surprisingly the cis-isomer showed better activity than the traps-isomer. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.01.024

文献信息

• Stereoselective synthesis of (2S,7S)-7-(4-phenoxymethyl)-2-(1-N-hydroxyureidyl-3-butyn-4-yl)oxepane: a potential anti-asthmatic drug candidate
  作者：Mukund K. Gurjar、B. Venkateswara Rao、L. Murali Krishna、Mukund S. Chorghade、Steven V. Ley

  DOI：10.1016/j.tetasy.2005.01.024

  日期：2005.3

  We have achieved a short, efficient stereoselective synthesis of 7-membered oxepane derivatives with potential against asthma. Highlights of our synthetic strategy are regioselective oxidation of a hydroxyl group and efficient ring closure of an open chain aldehyde to a 2-benzenesulfonyl oxepane derivative with PhSO2H. Surprisingly the cis-isomer showed better activity than the traps-isomer. (C) 2005 Elsevier Ltd. All rights reserved.