(+)-5-(1-(2-methoxynaphthalen-1-yl)naphthalen-2-yloxy)-1H-tetrazole

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+)-5-(1-(2-methoxynaphthalen-1-yl)naphthalen-2-yloxy)-1H-tetrazole
• 英文别名: (R)-(+)-5-(1-(2-methoxynaphthalen-1-yl)naphthalene-2-yloxy)-1H-tetrazole；(+)-5-(2'-methoxy-1,1'-binaphthalen-2-yloxy)-1H-tetrazole；5-[1-(2-methoxynaphthalen-1-yl)naphthalen-2-yl]oxy-2H-tetrazole
• 化学式: C₂₂H₁₆N₄O₂
• 分子量: 368.395
• InChiKey: LKVYGUVIGKBIRG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  72.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  对甲苯磺酰氯 、 (+)-5-(1-(2-methoxynaphthalen-1-yl)naphthalen-2-yloxy)-1H-tetrazole 在 三乙胺 作用下， 以 丙酮 为溶剂， 反应 2.0h， 以75%的产率得到2'-methoxy-1,1'-binaphthalen-2-yl (4-methylphenylsulfonyl)azidimidocarbonate
  参考文献：
  名称：

  Asymmetric syntheses with BINOL-based imidoyl azide

  摘要：

  Thermal decomposition of 2,4,6-trimethylphenyl and (+)-2'-methoxy-1,1'-binaphthalen-2-yl (4-methylphenylsulfonyl)azidimidocarbonates in the presence of norbornene, methyl acrylate, and camphene was studied. (+)-2'-Methoxy-1,1'-binaphthalen-2-yl (4-methylphenylsulfonyl)azidimidocarbonate reacted with norbornene to give (+)-exo-2'-methoxy-1,1'-binaphthalen-2-yl N-(4-methylphenylsulfonyl)-3-azatricyclo-[3.2.1.02,4]octane-3-carboximidoate, while in the reaction with methyl acrylate a mixture of stereoisomeric methyl 1-[(2'-methoxy-1,1'-binaphthalen-2-yloxy)(4-methylphenylsulfonylimino)methyl]aziridine-2-carboxylates was obtained. The reaction of 2,4,6-trimethylphenyl (4-methylphenylsulfonyl)azidimidocarbonate with (-)-camphene involved insertion of intermediate nitrene into the exocyclic double bond with formation of 2,4,6-trimethylphenyl N-(3,3-dimethylbicyclo[2.2.1]heptan-2-ylidenemethyl)-N'-(4-methylphenylsulfonyl)-imidocarbamate as a 3: 1 mixture of E,E and E,Z diastereoisomers in good yield.

  DOI：

  10.1134/s1070428008100114
• 作为产物：
  描述：

  (R)-2-羟基-2’-甲氧基-1,1’-联萘 在 sodium azide 、 三乙胺 作用下， 以 水 、 丙酮 为溶剂， 反应 3.0h， 生成 (+)-5-(1-(2-methoxynaphthalen-1-yl)naphthalen-2-yloxy)-1H-tetrazole
  参考文献：
  名称：

  具有轴向手性的芳氧基四唑：5-（1-（2-甲氧基萘-1-基）萘-2-基氧基）-1H-四唑的合成和部分拆分

  摘要：

  5-(1-(2-Methoxynaphthalen-1-yl)naphthalen-2-yloxy)-1H-四唑作为第一个具有轴手性的芳氧基四唑被合成。使用 (S)-脯氨酸和甲基苄胺作为拆分剂实现了部分拆分。使用含 75-85% ee 的甲基苄胺可获得最佳结果。© 2006 Wiley Periodicals, Inc. 杂原子化学 17:416–419, 2006; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20241

  DOI：

  10.1002/hc.20241

文献信息

• Aryloxy tetrazoles with axial chirality: Synthesis and partial resolution of 5-(1-(2-methoxynaphthalen-1-yl)naphthalen-2-yloxy)-1H-tetrazole
  作者：Hossein A. Dabbagh、Alireza Najafi Chermahini、Abbas Teimouri

  DOI：10.1002/hc.20241

  日期：——

  5-(1-(2-Methoxynaphthalen-1-yl)naph- thalen-2-yloxy)-1H-tetrazole as the first aryloxy tetrazole with axial chirality was synthesized. Partial resolution was achieved using (S)-proline and methylbenzylamine as the resolving agents. Best results were obtained using methylbenzylamine with 75–85% ee. © 2006 Wiley Periodicals, Inc. Heteroatom Chem 17:416–419, 2006; Published online in Wiley InterScience

  5-(1-(2-Methoxynaphthalen-1-yl)naphthalen-2-yloxy)-1H-四唑作为第一个具有轴手性的芳氧基四唑被合成。使用 (S)-脯氨酸和甲基苄胺作为拆分剂实现了部分拆分。使用含 75-85% ee 的甲基苄胺可获得最佳结果。© 2006 Wiley Periodicals, Inc. 杂原子化学 17:416–419, 2006; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20241
• A new family of bis-tetrazole (BIZOL) BINOL-type ligands
  作者：Hossein A. Dabbagh、Alireza Najafi-Chermahini、Soodabeh Banibairami

  DOI：10.1016/j.tetlet.2006.03.160

  日期：2006.6

  The synthesis and characterization of 5-(1-(2-(1H-tetrazole-5-yloxy)naphthalen-1-yl)naphthalen-2-yloxy)-1H-tetrazole (BIZOL) as the first bis-tetrazole BINOL-type ligands is described. (c) 2006 Elsevier Ltd. All rights reserved.
• Asymmetric syntheses with BINOL-based imidoyl azide
  作者：H. A. Dabbagh、A. Najafi Chermahini

  DOI：10.1134/s1070428008100114

  日期：2008.10

  Thermal decomposition of 2,4,6-trimethylphenyl and (+)-2'-methoxy-1,1'-binaphthalen-2-yl (4-methylphenylsulfonyl)azidimidocarbonates in the presence of norbornene, methyl acrylate, and camphene was studied. (+)-2'-Methoxy-1,1'-binaphthalen-2-yl (4-methylphenylsulfonyl)azidimidocarbonate reacted with norbornene to give (+)-exo-2'-methoxy-1,1'-binaphthalen-2-yl N-(4-methylphenylsulfonyl)-3-azatricyclo-[3.2.1.02,4]octane-3-carboximidoate, while in the reaction with methyl acrylate a mixture of stereoisomeric methyl 1-[(2'-methoxy-1,1'-binaphthalen-2-yloxy)(4-methylphenylsulfonylimino)methyl]aziridine-2-carboxylates was obtained. The reaction of 2,4,6-trimethylphenyl (4-methylphenylsulfonyl)azidimidocarbonate with (-)-camphene involved insertion of intermediate nitrene into the exocyclic double bond with formation of 2,4,6-trimethylphenyl N-(3,3-dimethylbicyclo[2.2.1]heptan-2-ylidenemethyl)-N'-(4-methylphenylsulfonyl)-imidocarbamate as a 3: 1 mixture of E,E and E,Z diastereoisomers in good yield.