(1S,2S)-2-[4-(2-fluoro-phenyl)piperazin-1-yl]-6,7-dimethoxy-1,2-dihydronaphthalen-1-ol | 1200184-90-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: (1S,2S)-2-[4-(2-fluoro-phenyl)piperazin-1-yl]-6,7-dimethoxy-1,2-dihydronaphthalen-1-ol
• 英文别名: (1S,2S)-2-[4-(2-fluorophenyl)piperazin-1-yl]-6,7-dimethoxy-1,2-dihydronaphthalen-1-ol
• CAS: 1200184-90-2
• 化学式: C₂₂H₂₅FN₂O₃
• 分子量: 384.451
• InChiKey: HDKQJTRQJOFDJN-UGKGYDQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  45.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-(2-氟苯基)哌嗪 、 6,7-dimethoxy-1,4-dihydro-1,4-epoxynaphthalene 在 碘化铵 、 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 (±)-2,2 '-二(二-对甲苯基膦)-1,1 '-联萘 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以38%的产率得到
  参考文献：
  名称：

  Iridium-Catalyzed Asymmetric Ring-Opening of Oxabenzonorbornadienes with N-Substituted Piperazine Nucleophiles

  摘要：

  报道了铱催化的氧杂苯并降冰片二烯与N-取代哌嗪的不对称开环反应。在2.5 mol% [Ir(COD)Cl]2和5.0 mol% (S)-对甲苯-BINAP的存在下，该反应以高产率和中等对映选择性提供了相应的开环产物。还研究了各种手性双齿配体、催化剂用量、溶剂和温度对产率和对映选择性的影响。基于产物2i的X射线结构，提出了一个合理的机理来解释相应反式开环产物的形成。

  DOI：

  10.3390/molecules201219748

文献信息

• Iridium-catalyzed asymmetric ring-opening reactions of oxabicyclic alkenes with secondary amine nucleophiles
  作者：Dingqiao Yang、Ping Hu、Yuhua Long、Yujuan Wu、Heping Zeng、Hui Wang、Xiongjun Zuo

  DOI：10.3762/bjoc.5.53

  日期：——

  Iridium-catalyzed asymmetric ring-opening reactions of oxabicyclic alkenes with various aliphatic and aromatic secondary amines are reported for the first time. The reaction gave the corresponding trans-1,2-dihydronaphthalenol derivatives in good yields with moderate enantioselectivities in the presence of 2.5 mol % [Ir(COD)Cl](2) and 5 mol % bisphosphine ligand (S)-p-Tol-BINAP. The trans-configuration

  首次报道了铱催化的氧杂环烯烃与各种脂肪族和芳香族仲胺的不对称开环反应。在 2.5 mol% [Ir(COD)Cl](2) 和 5 mol% 双膦配体 (S)-p-Tol-比纳普。X 射线晶体学证实了 3f 的反式构型。
• Iridium-Catalyzed Asymmetric Ring-Opening Reactions of Oxabenzonorbornadienes with Amine Nucleophiles
  作者：Dingqiao Yang、Yuhua Long、Junfang Zhang、Heping Zeng、Sanyong Wang、Chunrong Li

  DOI：10.1021/om100384q

  日期：2010.8.23

  We have explored a new iridium-catalyzed ring-opening reaction of oxabenzonorbornadienes with a variety of primary aromatic amine or N-substituted piperazine nucleophiles, affording the corresponding products in excellent yields (up to 99%) with moderate enantioselectivity (25−81% ee). The trans configuration of product 2d was confirmed by X-ray crystallography.

  我们探索了氧杂苯并降冰片二烯与各种伯芳族胺或N-取代的哌嗪亲核试剂的铱催化开环反应，从而以中等收率（25-81％ee）以优异的收率（高达99％）提供了相应的产物）。通过X射线晶体学确认产物2d的反式构型。
• Iridium-Catalyzed Asymmetric Ring-Opening of Oxabenzonorbornadienes with N-Substituted Piperazine Nucleophiles
  作者：Wen Yang、Renshi Luo、Dingqiao Yang

  DOI：10.3390/molecules201219748

  日期：——

  Iridium-catalyzed asymmetric ring-opening of oxabenzonorbornadienes with N-substituted piperazines was described. The reaction afforded the corresponding ring-opening products in high yields and moderate enantioselectivities in the presence of 2.5 mol % [Ir(COD)Cl]2 and 5.0 mol % (S)-p-Tol-BINAP. The effects of various chiral bidentate ligands, catalyst loading, solvent, and temperature on the yield and enantioselectivity were also investigated. A plausible mechanism was proposed to account for the formation of the corresponding trans-ring opened products based on the X-ray structure of product 2i.

  报道了铱催化的氧杂苯并降冰片二烯与N-取代哌嗪的不对称开环反应。在2.5 mol% [Ir(COD)Cl]2和5.0 mol% (S)-对甲苯-BINAP的存在下，该反应以高产率和中等对映选择性提供了相应的开环产物。还研究了各种手性双齿配体、催化剂用量、溶剂和温度对产率和对映选择性的影响。基于产物2i的X射线结构，提出了一个合理的机理来解释相应反式开环产物的形成。