1-(3,5-二苯基吡唑-1-基)乙酮 | 1154-63-8

• 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-(3,5-二苯基吡唑-1-基)乙酮
• 英文名称: 1-Acetyl-3,5-diphenylpyrazol
• 英文别名: 1-acetyl-3,5-diphenylpyrazole；1-acetyl-3,5-diphenyl-1H-pyrazole；1-(3,5-diphenyl-1H-pyrazol-1-yl)ethanone；1-(3,5-diphenylpyrazol-1-yl)ethanone
• CAS: 1154-63-8
• 化学式: C₁₇H₁₄N₂O
• 分子量: 262.311
• InChiKey: LEZLHOKJTQXBOW-UHFFFAOYSA-N

物化性质

• 溶解度：
  0.5 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933199090

反应信息

• 作为反应物：
  描述：

  1-(3,5-二苯基吡唑-1-基)乙酮 以37%的产率得到
  参考文献：
  名称：

  NITTA, MAKOTO;HAMAMATSU, TATSUO;MIYANO, HIROYUKI, BULL. CHEM. SOC. JAP., 61,(1988) N2, C. 4473-4475

  摘要：

  DOI：
• 作为产物：
  描述：

  苯甲醛 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 1-(3,5-二苯基吡唑-1-基)乙酮
  参考文献：
  名称：

  3,5-二芳基取代的2-吡唑啉的合成，表征和荧光研究

  摘要：

  在乙醇/ DMSO中，由α，β不饱和酮和水合肼与乙酸/甲酸合成了一系列2-吡唑啉。2-吡唑啉的结构已通过光谱技术确定，即UV，IR，1 H NMR，13 C NMR和微量元素分析。以固定的浓度和相同的激发波长在290 nm记录溶液中的荧光光谱。所有化合物的吸收带位置大致在280至336 nm之间，荧光带位置在300至370 nm（近紫外区域）之间。

  DOI：

  10.1016/j.saa.2010.12.053

文献信息

• Application of Fe3O4@SiO2@sulfamic acid magnetic nanoparticles as recyclable heterogeneous catalyst for the synthesis of imine and pyrazole derivatives in aqueous medium
  作者：B. Zakerinasab、M. A. Nasseri、H. Hassani、M. M. Samieadel

  DOI：10.1007/s11164-015-2204-1

  日期：2016.4

  Sulfamic acid supported on Fe3O4@SiO2 superpara magnetic nanoparticles was successfully applied as a recyclable solid acid catalyst with a large density of sulfamic acid groups for the synthesis of pyrazole derivatives, an important class of potentially bioactive compounds. The products are obtained in high yield from the one-pot reaction procedure involving dicarbonyl compounds and hydrazines/hydrazides. This new method totally avoids the use of toxic or expensive solvents and organic acids in this reaction.

  负载于Fe3O4@SiO2超顺磁性纳米颗粒上的氨基磺酸作为具有大量氨基磺酸基团的固态可回收酸性催化剂，成功应用于吡唑类衍生物的合成，这是一类潜在的生物活性化合物。通过活性双羰基化合物与肼/酰肼的一锅法反应，获得了高产率的目标产物。这种新方法完全避免了在该反应中使用有毒或昂贵的溶剂和有机酸。
• PEG–SO3H as a mild, efficient and green catalytic system for the synthesis of pyrazole derivatives in aqueous medium
  作者：M. A. Nasseri、S. A. Alavi、B. Zakeri Nasab

  DOI：10.1007/s13738-012-0143-y

  日期：2013.4

  A versatile, alternative and environmentally benign strategy for the synthesis of a series of pyrazoles has been successfully performed in water using PEG–SO3H as an acidic catalyst. The products are obtained in high yield from the one-pot reaction procedure involving dicarbonyl compounds and hydrazines/hydrazides. This new method totally avoids the use of organic acids and toxic or expensive solvents in this reaction. The catalyst is waste-free, easily prepared, and efficiently re-used.

  在水相中使用PEG-SO3H作为酸性催化剂，成功地实现了一种合成一系列吡唑类化合物的多功能、替代性及环境友好型策略。通过涉及二羰基化合物与酰肼/酰肼化合物的单锅反应程序，产物以高收率获得。该新方法完全避免了在此反应中使用有机酸和有毒或昂贵的溶剂。催化剂无废弃物产生，易于制备，并可高效重复使用。
• The Preparation of<i>N</i>-Acylpyrazoles and Their Behavior Toward Alcohols
  作者：Choji Kashima、Hajime Harada、Isanobu Kita、Iwao Fukuchi、Akira Hosomi

  DOI：10.1055/s-1994-25406

  日期：——

  According to four different methods, various types of N-acylpyrazoles were prepared from the corresponding pyrazoles and carboxylic acids or their acid chlorides. Although N-acylpyrazoles were inert to alcohols under neutral or weakly basic conditions, the alcoholysis was dramatically accelerated by the action of strong acid or base. On the basis of these chemical properties, the regioselective synthesis of methyl benzyl 2,2-dimethylglutarate was achieved by selective protection and functionalization of a carboxylic acid derivative using N-acylpyrazoles.

  根据四种不同的方法，从相应的吡唑和羧酸或其酰氯制备了多种类型的N-酰基吡唑。尽管在中性或弱碱性条件下，N-酰基吡唑对醇呈惰性，但强酸或碱的作用下，醇解反应显著加速。基于这些化学性质，通过选择性保护和功能化羧酸衍生物，成功实现了甲基苄基2,2-二甲基戊二酸酯的区域选择性合成。
• Synthesis of [3,3′(4<i>H</i>,4′<i>H</i>)-Bi-2<i>H</i>-1,3-oxazine]-4,4′-diones and Their Hydrolysis
  作者：Elif Korkusuz、İsmail Yıldırım

  DOI：10.1002/hlca.201200463

  日期：2013.7

  The [3,3′(4H,4′H)‐bi‐2H‐1,3‐oxazine]‐4,4′‐diones 3a–3i were obtained by [2+4] cycloaddition reactions of furan‐2,3‐diones 1a–1c with aromatic aldazines 2a–2d (Scheme 1). So, new derivatives of bi‐2H‐1,3‐oxazines and their hydrolysis products, 3,5‐diaryl‐1H‐pyrazoles 4a–4c (Scheme 3), which are potential biologically active compounds, were synthesized for the first time.

  的[3,3'（4 ħ，4' ħ）-bi-2 ħ -1,3-恶嗪] -4,4'-二酮3A - 3I是由[2 + 4]环加成的呋喃-2-反应获得，3-二酮1a - 1c与芳族醛嗪2a - 2d（方案1）。因此，首次合成了潜在的生物活性化合物bi-2 H -1,3-恶嗪的新衍生物及其水解产物3,5-二芳基-1 H-吡唑4a - 4c（方案3）。时间。
• Copper-catalyzed C–N cross-coupling of arylboronic acids with N-acylpyrazoles
  作者：Jin Zhang、Run-Ping Jia、Dong-Hui Wang

  DOI：10.1016/j.tetlet.2016.06.044

  日期：2016.8

  A copper-catalyzed C–N bond forming reaction of arylboronic acids and N-acylpyrazoles was developed. This procedure used N-acetyl protected pyrazoles as starting material instead of free pyrazoles (NH). The reaction worked under neutral conditions and did not require any base or ligand. The reaction showed good functional group tolerance.

  开发了一种铜催化的芳基硼酸与N-酰基吡唑的CN键形成反应。该方法使用N-乙酰基保护的吡唑代替游离吡唑（NH）作为起始原料。该反应在中性条件下进行，不需要任何碱或配体。反应显示出良好的官能团耐受性。