1-(苄氧基)吡唑 | 100159-47-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(苄氧基)吡唑
• 英文名称: 1-(benzyloxy)pyrazole
• 英文别名: 1-Benzyloxypyrazole；1-benzyloxy-1H-pyrazole；1-benzyloxy-pyrazol；1H-Pyrazole, 1-(phenylmethoxy)-；1-phenylmethoxypyrazole
• CAS: 100159-47-5
• 化学式: C₁₀H₁₀N₂O
• mdl: MFCD12026321
• 分子量: 174.202
• InChiKey: XQEPQBYKPDAGIZ-UHFFFAOYSA-N

物化性质

• 沸点：
  295.3±33.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 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)吡唑 在 一氯化碘 作用下， 生成 4-碘-1-(苯基甲氧基)-1H-吡唑
  参考文献：
  名称：

  N-Hydroxypyrazolyl Glycine Derivatives as Selective N-Methyl-d-aspartic Acid Receptor Ligands

  摘要：

  A series of analogues based on N-hydroxypyrazole as a bioisostere for the distal carboxylate group of aspartate have been designed, synthesized, and pharmacologically characterized. Affinity studies on the major glutamate receptor subgroups show that these 4-substituted N-hydroxypyrazol-5-yl glycine (NHP5G) derivatives are selectively recognized by N-methyl-D-aspartic acid (NMDA) receptors and that the (R)enantiomers are preferred. Moreover, several of the compounds are able to discriminate between individual subtypes among the NMDA receptors, providing new pharmacological tools. For example, 4-propyl NHP5G is an antagonist at the NR1/NR2A subtype but an agonist at the NR1/NR2D subtype. Molecular docking studies indicate that the substituent protrudes into a region that may be further exploited to improve subtype selectivity, thereby opening up a design strategy for ligands which can differentiate individual NMDA receptor subtypes.

  DOI：

  10.1021/jm800025e
• 作为产物：
  描述：

  1-benzyloxy-5-(tert-butyldiphenylsilyl)pyrazole 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 1-(苄氧基)吡唑
  参考文献：
  名称：

  Regioselective Introduction of Electrophiles in the 4-Position of 1-Hydroxypyrazole via Bromine−Lithium Exchange

  摘要：

  Two protocols for introduction of electrophiles at the 4-position of 1-hydroxypyrazoles have been developed. The first is deprotonation of 4-bromo-1-[(tert-butyldiphenylsilyl)oxy]pyrazole (6) with LDA to produce the 5-lithio derivative in which the silyl group migrates spontaneously from oxygen to C-5 affording 4-bromo-5-(tert-butyldiphenylsilyl)-1-lithoxypyrazole (8). Subsequent treatment with t-BuLi causes bromine-lithium exchange to give 5-tert-butyldiphenylsilyl-4-lithio-1-lithoxypyrazole which is trapped with electrophiles affording 4-substituted 5-(tert-butyldiphenylsilyl)-1-hydroxypyrazoles 9a-e in a one-pot sequence. The second is treatment of 4-bromo-1-hydroxypyrazole (5) with excess LDA and trimethylsilyl chloride to produce 3,5-bis(trimethylsilyl)-4-bromo-1-hydropyrazole (12), which upon sequential metalation with n-BuLi and reaction with electrophiles affords 4-substituted 3,5-bis(trimethylsilyl)-1-hydroxypyrazol 13a-e. The tert-butyldiphenylsilyl group of 9a and the trimethylsilyl groups of 12 can be removed selectively by treatment with tetrabutylammonium fluoride in THF in the presence of trifluoroacetic acid.

  DOI：

  10.1021/jo981970w

文献信息

• [EN] GLUCAGON RECEPTOR ANTAGONISTS, COMPOSITIONS, AND METHODS FOR THEIR USE<br/>[FR] ANTAGONISTES DU RÉCEPTEUR DE GLUCAGON, COMPOSTIONS ET PROCÉDÉ D'UTILISATION DE CES COMPOSÉS
  申请人：SCHERING CORP

  公开号：WO2009140342A1

  公开（公告）日：2009-11-19

  The present invention relates to compounds of general formula (I), wherein ring A, ring B, R1, R2, R3, Z, and L1 are selected independently of each other and are as defined herein, to compositions comprising the compounds, and methods of using the compounds as glucagon receptor antagonists and for the treatment or prevention of type 2 diabetes and conditions related thereto.

  本发明涉及一般式(I)的化合物，其中环A、环B、R1、R2、R3、Z和L1彼此独立选择，并如本文所定义，涉及包含该化合物的组合物，以及将该化合物用作胰高血糖素受体拮抗剂并用于治疗或预防2型糖尿病及相关疾病的方法。
• Heterocyclic sulfonamide inhibtors of beta amyloid production containing an azole
  申请人：Resnick Lynn

  公开号：US20050171180A1

  公开（公告）日：2005-08-04

  Compounds useful for lowering beta amyloid levels are provided. The compounds have the structure of formula Ia: wherein, R 1 is lower alkyl, substituted lower alkyl, phenyl, substituted phenyl, benzyl, substituted benzyl, benzyloxy, substituted benzyloxy, or SO 2 R 5 ; R 5 is phenyl, substituted phenyl, heterocycle, substituted heterocycle, alkyl, or substituted alkyl; R 2 is lower alkyl, substituted lower alkyl, CF 3 , alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, phenyl, substituted phenyl, or cycloalkyl; R 3 is hydrogen, lower alkyl, or substituted lower alkyl; R 4 is phenyl, substituted phenyl, heterocycle, substituted heterocycle, thiophene, or substituted thiophene; R 6 is hydrogen, lower alkyl, substituted lower alkyl, CF 3 , alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, phenyl, substituted phenyl, cycloalkyl, or substituted cycloalkyl; W, X and Y are independently CR 7 or N; and R 7 is hydrogen, halogen, lower alkyl, or substituted lower alkyl.

  提供了降低β淀粉样蛋白水平的化合物。这些化合物具有如下式Ia的结构：其中，R1是较低的烷基，取代的较低烷基，苯基，取代的苯基，苄基，取代的苄基，苄氧基，取代的苄氧基，或SO2R5；R5是苯基，取代的苯基，杂环，取代的杂环，烷基，或取代的烷基；R2是较低的烷基，取代的较低烷基，CF3，烯基，取代的烯基，炔基，取代的炔基，苯基，取代的苯基，或环烷基；R3是氢，较低的烷基，或取代的较低烷基；R4是苯基，取代的苯基，杂环，取代的杂环，噻吩，或取代的噻吩；R6是氢，较低的烷基，取代的较低烷基，CF3，烯基，取代的烯基，炔基，取代的炔基，苯基，取代的苯基，环烷基，或取代的环烷基；W、X和Y独立地是CR7或N；而R7是氢，卤素，较低的烷基，或取代的较低烷基。
• Pyrazolyl benzyl ethers
  申请人：——

  公开号：US20030109702A1

  公开（公告）日：2003-06-12

  The invention relates to novel pyrazolyl benzyl ethers, to a process for their preparation and to their use for controlling harmful organisms.

  这项发明涉及新型吡唑基苄醚，以及用于其制备的方法和用于控制有害生物的用途。
• Synthesis of a new analogue of BINOL based on a homodimer of substituted 1-hydroxypyrazole
  作者：Øystein Rist、Mikael Begtrup

  DOI：10.1039/b010126p

  日期：——

  A new potential ligand for asymmetric synthesis, based on a homodimer of 1-hydroxypyrazole, has been synthesized. The chemistry involved lithiation, iodine–magnesium exchange, magnesium–zinc exchange, and cross-coupling reactions. In a preliminary study, the chemical activity of the ligand as a titanium(IV) complex was investigated in the addition of diethyl zinc to benzaldehyde. Its activity was comparable to the corresponding BINOL–Ti(IV) complex.

  一种基于1-羟基吡唑的同源二聚体的新型潜在配体已被合成。该化学反应涉及锂化、碘-镁交换、镁-锌交换和交叉耦合反应。在初步研究中，探讨了该配体作为钛(IV)络合物在二乙基锌与苯甲醛加成反应中的化学活性。其活性与相应的BINOL-Ti(IV)络合物相当。
• Regioselective acylation of 1-hydroxypyrazoles via metalated intermediates
  作者：Niels Østergaard、Niels Skjærbæk、Mikael Begtrup、Per Vedsø

  DOI：10.1039/b107850j

  日期：2002.1.23

  A range of C-4 and C-5 acylated 1-benzyloxypyrazoles (7a–e) and (4) have been prepared via Pd(0) catalysed cross-coupling between acid chlorides and 1-benzyloxy-4-(tributylstannyl)pyrazole (8) or 1-benzyloxypyrazol-5-ylzinc chloride. 3-Acylated 2-(4-methoxybenzyl)-2H-pyrazole 1-oxides (15a–f) were formed by reaction between the 3-magnesiated 2H-pyrazole 1-oxide (14) and acid chlorides. The benzyl group of 4 and 7a and the 4-methoxybenzyl (PMB) group of 15a were removed by treatment with conc. HCl or TFA in the presence of water, furnishing the corresponding C-acylated 1-hydroxypyrazoles.

  通过钯（0）催化酸氯化物与 1-苄氧基-4-(三丁基锡烷基)吡唑（8）或 1-苄氧基吡唑-5-基氯化锌之间的交叉偶联，制备了一系列 C-4 和 C-5 乙酰化 1-苄氧基吡唑（7a-e）和（4）。通过 3-镁化 2H-吡唑 1-氧化物（14）与酸氯化物反应，生成 3-酰化 2-（4-甲氧基苄基）-2H-吡唑 1-氧化物（15a-f）。4 和 7a 的苄基以及 15a 的 4-甲氧基苄基（PMB）通过在有水的情况下用浓盐酸或反式脂肪酸处理去除，得到相应的 C-酰化的 1-羟基吡唑。