1-benzyloxy-5-formylpyrazole | 166820-31-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-benzyloxy-5-formylpyrazole
• 英文别名: 1-(benzyloxy)-1H-pyrazole-5-carbaldehyde；2-phenylmethoxypyrazole-3-carbaldehyde
• CAS: 166820-31-1
• 化学式: C₁₁H₁₀N₂O₂
• 分子量: 202.213
• InChiKey: FZTCOCOIYQPMRJ-UHFFFAOYSA-N

物化性质

• 沸点：
  366.7±44.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-benzyloxy-5-formylpyrazole 在 sodium tetrahydroborate 、 氯化亚砜 作用下， 以 甲醇 为溶剂， 反应 1.5h， 生成 1-benzyloxy-5-chloromethylpyrazole
  参考文献：
  名称：

  谷氨酸的新型1-羟基唑生物等排体。合成，蛋白水解性质和药理学。

  摘要：

  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）=

  DOI：

  10.1021/jm010303j
• 作为产物：
  描述：

  N,N-二甲基甲酰胺 、 1-(苄氧基)吡唑 在 四甲基乙二胺 盐酸 、 正丁基锂 作用下， 生成 1-benzyloxy-5-formylpyrazole
  参考文献：
  名称：

  Synthesis of 5-Substituted 1-Hydroxypyrazoles through Directed Lithiation of 1-(Benzyloxy)pyrazole

  摘要：

  1-Hydroxypyrazoles have been converted to 1-(benzyloxy), [(9-phenylfluorenyl)oxy], [(N,N-diethylcarbamoyl)oxy], and (-silyloxy)pyrazoles. 1-(Benzyloxy)pyrazole was lithiated selectively in the 5-position. Subsequent reaction with electrophiles gives rise to 1-(benzyloxy)pyrazole with carbon, halogen, silicon, sulfur, or tin substituents at the 5-position. 1-(Benzyloxy)pyrazoles could be debenzylated by hydrogen bromide or hydrogenolysis producing 5-substituted 1-hydroxypyrazoles in high overall yield.

  DOI：

  10.1021/jo00121a017

文献信息

• Porphyrins with four azole substituents in meso positions. Part 2. X-ray crystal structure of meso-tetrakis {1-[2-(trimethylsilyl)ethoxymethyl]pyrazol-5-yl}-porphyrin at 200 K
  作者：Ana Sánchez-Migallón、Antonio de la Hoz、Mikael Begtrup、Cristina Fernández-Castaño、Concepción Foces-Foces、José Elguero

  DOI：10.1016/0040-4020(96)00602-3

  日期：1996.8

  The crystal and molecular structure of meso-tetrakis 1-[2-(trimethylsilyl) ethoxymethyl]pyrazol-5-yl porphyrin 2 has been solved by X-ray analysis. The porphyrin core appears to be distorted from planarity and the conformation of the pyrazole rings is such that pyrazole N2 atoms are situated up, up, down, down with regard to the macrocyclic ring (ααββ atropisomer). A new porphyrin meso-tetrakis[1-

  通过X射线分析已经解决了内消旋-四[1- [2-（三甲基甲硅烷基）乙氧基甲基]吡唑-5-基卟啉2的晶体和分子结构。卟啉核似乎从平面度变形，并且吡唑环的构象使得吡唑N 2原子相对于大环（ααββ阻转异构体）位于上，上，下，下。一种新的卟啉的内消旋-四[1-苄氧基-3-甲基吡唑-5-基] -卟啉3已经从1-苄基-5-甲酰基吡唑获得。已经制备了内消旋-四-（1-苄基吡唑-4-基）卟啉1的Zn（II）和Co（III）配合物，并通过MS，NMR和UV进行了表征。
• Novel 5-substituted 1-pyrazolol analogues of ibotenic acid: Synthesis and pharmacology at glutamate receptors
  作者：Charlotte G. Jørgensen、Hans Bräuner-Osborne、Birgitte Nielsen、Jan Kehler、Rasmus P. Clausen、Povl Krogsgaard-Larsen、Ulf Madsen

  DOI：10.1016/j.bmc.2007.02.047

  日期：2007.5

  5-Substituted 1-pyrazolol analogues of ibotenic acid have been synthesized and pharmacologically characterized on ionotropic and metabotropic glutamate receptors (iGluRs and mGluRs). The syntheses involved introduction of bromide, alkyls, phenyl and arylalkyls in the 5-position of 1-benzyloxypyrazole leading to 5-substituted (RS)-2-amino-(1-hydroxy-4-pyrazolyl)acetic acids (5a-1). The pharmacological activities of the synthesized analogues ranged from the 5-cyclopropylmethyl analogue (5f) with weak but selective affinity for NMDA receptors (IC50 = 35 mu M), over the 5-n-propyl analogue (5c), which was a selective mGluR2 agonist (EC50 = 72 mu M), to the 5-cyclohexylmethyl analogue (5g), which was a selective mGluR2 antagonist (K-i = 32 mu M), and the 5-phenylethyl analogue (5j), which was a weak but apparently selective mGluR1 antagonist (K-i = 230 mu M). This series of compounds afforded GluR ligands with a broad spectrum of pharmacological profiles, and showing potential for development of new compounds with subtype-selective activities at various GluRs. (c) 2007 Elsevier Ltd. All rights reserved.
• 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 5-Substituted 1-Hydroxypyrazoles through Directed Lithiation of 1-(Benzyloxy)pyrazole
  作者：Per Vedso、Mikael Begtrup

  DOI：10.1021/jo00121a017

  日期：1995.8

  1-Hydroxypyrazoles have been converted to 1-(benzyloxy), [(9-phenylfluorenyl)oxy], [(N,N-diethylcarbamoyl)oxy], and (-silyloxy)pyrazoles. 1-(Benzyloxy)pyrazole was lithiated selectively in the 5-position. Subsequent reaction with electrophiles gives rise to 1-(benzyloxy)pyrazole with carbon, halogen, silicon, sulfur, or tin substituents at the 5-position. 1-(Benzyloxy)pyrazoles could be debenzylated by hydrogen bromide or hydrogenolysis producing 5-substituted 1-hydroxypyrazoles in high overall yield.