1-(苄氧基)-1H-咪唑 | 121779-19-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1-(苄氧基)-1H-咪唑
• 英文名称: 1-(benzyloxy)imidazole
• 英文别名: 1-(benzyloxy)-1H-imidazole；1-phenylmethoxyimidazole
• CAS: 121779-19-9
• 化学式: C₁₀H₁₀N₂O
• mdl: MFCD01814553
• 分子量: 174.202
• InChiKey: AGJCQEWHSOFIOP-UHFFFAOYSA-N

物化性质

• 熔点：
  31-33 °C
• 沸点：
  150 °C(Press: 0.05 Torr)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(苄氧基)-1H-咪唑 在 正丁基锂 、 六氯乙烷 作用下， 生成 1-(benzyloxy)-2-chloroimidazole
  参考文献：
  名称：

  Synthesis of 2-Substituted 1-Hydroxyimidazoles through Directed Lithiation

  摘要：

  Benzylation of 3-hydroxyimidazole 1-oxide gave 3-(benzyloxy)imidazole 1-oxide, which was deoxygenated with phosphorous trichloride to produce 1-(benzyloxy)imidazole. 1-(Benzyloxy)imidazole was deprotonated selectively at C-2 by n-butyllithium. The anion formed was reacted with electrophiles to give 1-(benzyloxy)imidazoles with carbon; halogen, silicon, or sulfur substituents at the 2-position, Subsequent debenzylation afforded 2-substituted 1-hydroxaimidazoles which in turn could be deoxygenated to give 2-substituted imidazoles.

  DOI：

  10.1021/jo970355+
• 作为产物：
  描述：

  1-苄氧基咪唑3-氧化物 在 三氯化磷 作用下， 以 氯仿 为溶剂， 生成 1-(苄氧基)-1H-咪唑
  参考文献：
  名称：

  Pinto, Luis F. V.; Justino, Goncalo C.; Vieira, Abel J. S. C., ARKIVOC, 2010, vol. 2010, # 5, p. 17 - 23

  摘要：

  DOI：

文献信息

• Novel 1-Hydroxyazole Bioisosteres of Glutamic Acid. Synthesis, Protolytic Properties, and Pharmacology
  作者：Tine B. Stensbøl、Peter Uhlmann、Sandrine Morel、Birgitte L. Eriksen、Jakob Felding、Hasse Kromann、Mette B. Hermit、Jeremy R. Greenwood、Hans Braüner-Osborne、Ulf Madsen、Finn Junager、Povl Krogsgaard-Larsen、Mikael Begtrup、Per Vedsø

  DOI：10.1021/jm010303j

  日期：2002.1.1

  synaptosomal [3H]D-aspartic acid uptake (IC(50) = 93 +/- 25 microM), as well as excitatory amino acid transporters (EAATs) EAAT1 (IC(50) = 100 +/- 30 microM) and EAAT2 (IC(50) = 300 +/- 80 microM). By contrast, compound 8b showed no appreciable affinity for Glu uptake sites, neither synaptosomal nor cloned. Compounds 9a-c and 10a,b, possessing 1-hydroxyimidazole as the terminal acidic function, were devoid

  合成了多种1-羟基唑衍生物，作为（S）-谷氨酸（Glu）的生物等排体和AMPA受体激动剂（R，S）-2-氨基-3-（3-羟基-5-甲基- 4-异恶唑基）丙酸（AMPA，3b）。所有化合物均进行了体外药理研究，包括一系列Glu受体结合测定，天然和克隆Glu摄取系统的摄取研究以及电生理大鼠皮层切片模型。化合物7a，b（带有1-羟基-5-吡唑基部分作为远端羧基官能团的AMPA类似物）仅对[3H] AMPA受体结合位点具有中等亲和力（IC（50）= 2.7 +/- 0.4 microM和IC （50）分别为2.6 +/- 0.6 microM），与大鼠皮质楔形模型的电生理数据相关（EC（50）= 280 +/- 48 microM，EC（50）= 586 +/- 41 microM，分别）。化合物8a，b的AMPA的1-羟基-1,2,3-三唑-5-基类似物对[3H] AMPA受体结合位点表现出高亲和力（IC（50）=
• Synthesis of 4- and 5-Substituted 1-Hydroxyimidazoles through Directed Lithiation and Metal−Halogen Exchange
  作者：Birgitte Langer Eriksen、Per Vedsø、Mikael Begtrup

  DOI：10.1021/jo001554n

  日期：2001.12.1

  regioselectively at the 4-position of 1-(benzyloxy)imidazole by bromine-lithium exchange of 4-bromo-2-chloro-1-(benzyloxy)imidazoles, protected at C-5 with chloro or trimethylsilyl groups, followed by reaction with an electrophile. The 5-(trimethylsilyl) group was removed via base-catalyzed desilylation. Chlorine at C-2 and O-benzyl groups were removed by palladium-catalyzed hydrogenolysis.

  在用氯或三甲基甲硅烷基保护C-2之后，通过在C-5锂化，将亲电试剂选择性地引入1-（苄氧基）咪唑的5-位。随后用亲电试剂处理，得到5-取代的1-（苄氧基）-2-氯咪唑8-13和5-取代的1-（苄氧基）咪唑3-5，在处理过程中失去了2-（三甲基甲硅烷基）基团。通过4-溴-2-氯-1-（苄氧基）咪唑的溴-锂交换将亲电试剂选择性引入1-（苄氧基）咪唑的4-位，然后在C-5处用氯或三甲基甲硅烷基保护，然后与亲电试剂反应。通过碱催化的甲硅烷基化除去5-（三甲基甲硅烷基）基团。通过钯催化的氢解除去C-2和O-苄基上的氯。
• 1-Hydroxyimidazole Derivatives III.^1,2Synthesis of 1-Alkyloxy-, 1-Arylalkyloxy-, and 1-Phenoxy-1<i>H</i>-imidazoles
  作者：Gerhard Laus、Josef Stadlwieser、Wilhelm Klötzer

  DOI：10.1055/s-1989-27392

  日期：——

  1-Hydroxy-1H-imidazole and 2-alkyl-1-hydroxy-1H-imidazoles are prepared by selective hydrogenation of the corresponding 1-hydroxy-1H-imidazole 3-oxides and subsequently transformed to the 1-alkoxy, 1-arylalkyloxy and 1-phenoxy derivatives.

  通过选择性氢化相应的 1-hydroxy-1H-imidazole 3-oxides 制备 1-羟基-1H-咪唑和 2-烷基-1-羟基-1H-咪唑，然后转化为 1-烷氧基、1-芳基烷氧基和 1-苯氧基衍生物。
• Novel Tyrosinase inhibitors and pharmaceutical/cosmetic applications thereof
  申请人：Suzuki Itaru

  公开号：US20100010049A1

  公开（公告）日：2010-01-14

  Compounds corresponding to the following general formula (I): are formulated into pharmaceutical compositions useful in human or veterinary medicine or else into cosmetic compositions; novel compounds of formula (II) are also thus useful:

  符合以下通式（I）的化合物可制成人类或兽医药物或化妆品；通式（II）的新化合物也可如此使用。
• THIENO [2, 3-B] PYRIDINE DERIVATIVES AS VIRAL REPLICATION INHIBITORS
  申请人：Bardiot Dorothée

  公开号：US20120059028A1

  公开（公告）日：2012-03-08

  The present invention relates to a series of compounds having antiviral activity, more specifically HIV (Human Immunodeficiency Virus) replication inhibiting properties. The invention also relates to methods for the preparation of such compounds, as well as to novel intermediates useful in one or more steps of such syntheses. The invention also relates to pharmaceutical compositions comprising an effective amount of such compounds as active ingredients. This invention further relates to the use of such compounds as medicines or in the manufacture of a medicament useful for the treatment of animals suffering from viral infections, in particular HIV infection. This invention further relates to methods for the treatment of viral infections in animals by the administration of a therapeutic amount of such compounds, optionally combined with one or more other drugs having anti-viral activity.

  本发明涉及一系列具有抗病毒活性的化合物，更具体地说是具有抑制人类免疫缺陷病毒（HIV）复制的特性。本发明还涉及制备这种化合物的方法，以及在这些合成步骤中有用的新型中间体。本发明还涉及含有这种化合物作为活性成分的有效剂量的制药组合物。此外，本发明还涉及将这种化合物用作药物或用于制造对治疗患有病毒感染，特别是HIV感染的动物有用的药物。此外，本发明还涉及通过给予治疗量的这种化合物的管理，可选地与一个或多个具有抗病毒活性的其他药物结合，用于治疗动物的病毒感染的方法。

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