1-Benzyloxy-5-iodopyrazole | 166820-35-5

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 1-Benzyloxy-5-iodopyrazole
• 英文别名: 5-Iodo-1-phenylmethoxypyrazole
• CAS: 166820-35-5
• 化学式: C₁₀H₉IN₂O
• 分子量: 300.099
• InChiKey: NHNOPVOTYWPBLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 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-Benzyloxy-5-iodopyrazole 在 盐酸 作用下， 反应 1.0h， 以89%的产率得到1-hydroxy-5-iodopyrazole
  参考文献：
  名称：

  N-Alkoxypyrazoles as biomimetics for the alkoxyphenyl group in tamoxifen

  摘要：

  The preparation of a series of novel analogues of the selective antiestrogen tamoxifen is reported. 1Z-alkoxyphenyl group in tamoxifen has been replaced by a N-alkoxypyrazole, while functionalised phenyl groups or heteroaromatics were introduced at the 2Z-position using sequential Suzuki cross coupling of 1,2-(bis)borylpinacol 1-phenylbutene with 4- or 5-iodo-1-N,N-dimethylaminoethyl or propyl-pyrazoles. Approximately 50 tamoxifen analogues were obtained and tested in an estrogen receptor (ERalpha) affinity assay. Several compounds exhibited binding affinities 2-5-fold lower than tamoxifen. Dose-response experiments with six selected compounds were carried out using two different human breast cancer cell lines, MCF-7 and the tamoxifen resistant cell line MCF-/TAM(R)-1. Both cell lines exhibited growth inhibition upon treatment with the tamoxifen analogues. Co-treatment of the cells, with estradiol and the individual compounds, were also performed. The results indicated that the observed growth inhibitory effect was mediated by the ERalpha. Analogues of the potent antiestrogen 4-hydroxytamoxifen (4-OHT) were synthesised where the 1E-4-hydroxyphenyl was replaced by a 1-hydroxypyrazol-4-yl group. However, modest growth inhibition of MCF-7 cells was observed upon treatment with these analogues. In contrast, 1Z-, 2Z-ringclosed tamoxifen analogue (59) was shown to possess antiproliferative effects on MCF-7 and MCF-/TAM(R)-1 cells in lower doses than tamoxifen. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00566-7
• 作为产物：
  描述：

  1-(苄氧基)吡唑 在 四甲基乙二胺 正丁基锂 、 碘 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以94%的产率得到1-Benzyloxy-5-iodopyrazole
  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

• 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。
• Preparation of 5-Acyl- and 5-Aryl-Substituted 1-(Benzyloxy)pyrazoles via Directed Ortho-Lithiation/Transmetalation and Palladium Catalyzed Cross-Coupling
  作者：Jesper Kristensen、Mikael Begtrup、Per Vedsø

  DOI：10.1055/s-1998-2201

  日期：1998.11
• Palladium-Catalyzed Arylation and Acylation of 1-Benzyloxy-1,2,3-triazole Through a Directed Ortho Lithiation-Transmetalation Strategy
  作者：Jakob Felding、Peter Uhlmann、Jesper Kristensen、Per Vedsø、Mikael Begtrup

  DOI：10.1055/s-1998-2131

  日期：1998.8