2-[(1R)-1-azidoethyl]naphthalene | 176315-15-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-[(1R)-1-azidoethyl]naphthalene
• CAS: 176315-15-4
• 化学式: C₁₂H₁₁N₃
• 分子量: 197.239
• InChiKey: OYDIIQABGXOBJL-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  14.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-[(1R)-1-azidoethyl]naphthalene 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以961 mg的产率得到(R)-(+)-1-(2-萘基)乙胺
  参考文献：
  名称：

  探测酶的立体特异性。手性胺和氨基醇衍生物对α-胰凝乳蛋白酶和枯草杆菌蛋白酶Carlsberg的抑制作用

  摘要：

  已经评估了各种对映体胺和氨基醇酰胺以及α-酮酰胺衍生物作为代表性丝氨酸蛋白酶α-胰凝乳蛋白酶（CT）和枯草杆菌蛋白酶Carlsberg（SC）的竞争性抑制剂。研究的每种化合物都是两种酶的有效竞争抑制剂。然而，仅对于最佳抑制剂，N-丙酮酰-1-（1-萘基）乙胺（对于CT的S-对映异构体，K 1 27μM）是值得注意的对映异构体区别，其中S-对映异构体明显更有效CT和SC的抑制剂比R-分别对应12.6和73倍的因子。通过分子模型分析揭示了负责这种强结合和对映异构的酶-抑制剂相互作用。

  DOI：

  10.1016/0040-4020(96)00078-6
• 作为产物：
  描述：

  (S)-(-)-1-(2-萘基)乙醇 在 叠氮基三甲基硅烷 、 二苯基亚磷酸苯酚酯 、 三甲基硅基甲基叠氮化物 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以85%的产率得到2-[(1R)-1-azidoethyl]naphthalene
  参考文献：
  名称：

  Stereospecific Synthesis ofsec- andtert-Alkyl Azides from Alcohols and Trimethylsilyl Azide by a New Type of Oxidation–Reduction Condensation Using Phenyl Diphenylphosphinite and Trimethylsilylmethyl Azide

  摘要：

  描述了一种利用苯基二苯基亚次膦酸酯和三甲基甲硅烷基叠氮化物通过新型氧化还原缩合从醇和三甲基甲硅烷基叠氮化物制备烷基叠氮化物的新方法。手性仲醇和叔醇在温和和中性条件下转化为相应的手性叠氮化物，构型几乎完全反转。

  DOI：

  10.1246/cl.2008.1072

文献信息

• Nicotinoyl Azide (NCA)-Mediated Mitsunobu Reaction: An Expedient One-Pot Transformation of Alcohols into Azides
  作者：Gianluca Papeo、Helena Posteri、Paola Vianello、Mario Varasi

  DOI：10.1055/s-2004-831254

  日期：——

  A practical and simple method that allows preparation of azides from alcohols is described. The process involves oxyphosphonium-type activation and it is based upon the use of nicotinoyl azide (NCA), a cheap and easily accessible azide ion source.

  描述了一种实用而简便的方法，允许从醇类制备叠氮化合物。该过程涉及氧膦型活化，并基于使用烟酰叠氮（NCA），这是一种廉价且易于获得的叠氮离子源。
• Stereospecific Synthesis of<i>sec</i>- and<i>tert</i>-Alkyl Azides from Alcohols and Trimethylsilyl Azide by a New Type of Oxidation–Reduction Condensation Using Phenyl Diphenylphosphinite and Trimethylsilylmethyl Azide
  作者：Teruaki Mukaiyama、Kiichi Kuroda、Yuji Maruyama、Yujiro Hayashi

  DOI：10.1246/cl.2008.1072

  日期：2008.10.5

  A novel method for the preparation of alkyl azides from alcohols and trimethylsilyl azide by a new type of oxidation–reduction condensation using phenyl diphenylphosphinite and trimethylsilylmethyl azide is described. Chiral secondary and tertiary alcohols are converted into the corresponding chiral azides with almost complete inversion of configuration under mild and neutral conditions.

  描述了一种利用苯基二苯基亚次膦酸酯和三甲基甲硅烷基叠氮化物通过新型氧化还原缩合从醇和三甲基甲硅烷基叠氮化物制备烷基叠氮化物的新方法。手性仲醇和叔醇在温和和中性条件下转化为相应的手性叠氮化物，构型几乎完全反转。
• Chiroptical Probing of Lanthanide-Directed Self-Assembly Formation Using btp Ligands Formed in One-Pot Diazo-Transfer/Deprotection Click Reaction from Chiral Amines
  作者：Joseph P. Byrne、Miguel Martínez-Calvo、Robert D. Peacock、Thorfinnur Gunnlaugsson

  DOI：10.1002/chem.201504257

  日期：2016.1.11

  A series of enantiomeric 2,6‐bis(1,2,3‐triazol‐4‐yl)pyridines (btp)‐containing ligands was synthesized by a one‐pot two‐step copper‐catalyzed amine/alkyne click reaction. The EuIII‐ and TbIII‐directed self‐assembly formation of these ligands was studied in CH3CN by monitoring their various photophysical properties, including their emerging circular dichroism and circularly polarized luminescence. The

  通过一锅两步铜催化的胺/炔点击反应合成了一系列对映体2,6-双（1,2,3-三唑-4-基）吡啶（btp）配体。通过监测CH 3 CN的各种光物理性质，包括新兴的圆二色性和圆偏振发光，研究了这些配体的Eu III和Tb III定向自组装形成。对前者的整体分析使得能够确定溶液中各种手性超分子物种的化学计量和稳定性常数。
• Kinetic resolution by copper-catalyzed azide–alkyne cycloaddition
  作者：Jun-cai Meng、Valery V. Fokin、M.G. Finn

  DOI：10.1016/j.tetlet.2005.05.019

  日期：2005.7

  The use of chiral pybox ligands imparts enantioselectivity to the Cu-I-catalyzed azide-alkyne cycloaddition reaction, in the form of kinetic resolution of alpha-chiral azides and desymmetrization of gem-diazides. While levels of selectivity are modest, the results show unequivocally that the process benefits from ligand-accelerated catalysis. (c) 2005 Elsevier Ltd. All rights reserved.
• A New Type of Oxidation-Reduction Condensation by the Combined Use of Phenyl Diphenylphosphinite and Oxidant
  作者：Teruaki Mukaiyama、Kiichi Kuroda、Yuji Maruyama

  DOI：10.3987/rev-09-sr(s)1

  日期：——

  A new type of oxidation-reduction condensation of alcohols with sulfur, nitrogen, and oxygen nucleophiles by the combined use of phenyl diphenylphosphinite (PhOPPh2) and oxidants such as azides or diethyl azodicarboxylate (DEAD) are described. In these reactions, chiral secondary and tertiary alcohols are converted into the corresponding chiral sulfides, azides, esters and ethers under mild and neutral conditions with almost complete inversion of stereochemical configuration.