1-对甲苯基-4,5-二氢-1H-吡唑 | 34946-99-1

• 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-对甲苯基-4,5-二氢-1H-吡唑
• 英文名称: 1-(p-tolyl)-4,5-dihydro-1H-pyrazole
• 英文别名: 1-P-Tolyl-4,5-dihydro-1H-pyrazole；2-(4-methylphenyl)-3,4-dihydropyrazole
• CAS: 34946-99-1
• 化学式: C₁₀H₁₂N₂
• mdl: MFCD09032133
• 分子量: 160.219
• InChiKey: ORDKRLFWJUCKCT-UHFFFAOYSA-N

物化性质

• 沸点：
  277.6±33.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  15.6
• 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-对甲苯基-4,5-二氢-1H-吡唑 、 乙醇 、 alkaline earth salt of/the/ methylsulfuric acid 生成 N-(3-aminopropyl)-p-toluidine
  参考文献：
  名称：

  Balbiano, Gazzetta Chimica Italiana, 1888, vol. 18, p. 358

  摘要：

  DOI：
• 作为产物：
  描述：

  N-3-Brompropyl-p-toluidin 在 iron(III) chloride 、 sodium azide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 80.0~100.0 ℃ 、101.33 kPa 条件下， 反应 13.0h， 生成 1-对甲苯基-4,5-二氢-1H-吡唑
  参考文献：
  名称：

  Fe(III)-Catalyzed Aerobic Intramolecular N–N Coupling of Aliphatic Azides with Amines

  摘要：

  An Fe(III)-catalyzed intramolecular N-N coupling of aliphatic azidoamines that forms diverse five-and six-membered semisaturated diazoheterocycles using air as an oxidant is reported, providing an alternative to hydrazine-based methods. Mechanistic studies suggest that a N-radical induced intramolecular homolytic substitution (S(H)2) is involved in ring closure. The power of this N-N bond-forming method is also demonstrated by using it as the final step in a total synthesis of (-)-newbouldine.

  DOI：

  10.1021/acs.orglett.9b01396

文献信息

• Microwave-assisted cyclocondensation of hydrazine derivatives with alkyl dihalides or ditosylates in aqueous media: syntheses of pyrazole, pyrazolidine and phthalazine derivatives
  作者：Yuhong Ju、Rajender S. Varma

  DOI：10.1016/j.tetlet.2005.07.018

  日期：2005.9

  Direct syntheses of 4,5-dihydro-pyrazole, pyrazolidine, and 1,2-dihydro-phthalazine derivatives via double-alkylation of hydrazines by alkyl dihalides or ditosylates were accomplished in aqueous media under microwave irradiation conditions; the environmentally friendlier chemical transformation occurred in a single step and eliminated the use of expensive metal catalysts in building two C–N bonds.

  在微波辐射条件下，在含水介质中，通过烷基二卤化物或二甲苯磺酸盐对肼的双烷基化反应，直接合成4，5-二氢吡唑，吡唑烷和1，2-二氢邻苯二甲酰肼衍生物。有利于环境的化学转化过程一步完成，消除了使用昂贵的金属催化剂来构建两个C–N键的过程。
• Ruthenium-Catalyzed Divergent Acceptorless Dehydrogenative Coupling of 1,3-Diols with Arylhydrazines: Synthesis of Pyrazoles and 2-Pyrazolines
  作者：Yanling Zheng、Yang Long、Huihua Gong、Jiaqi Xu、Chunchun Zhang、Haiyan Fu、Xueli Zheng、Hua Chen、Ruixiang Li

  DOI：10.1021/acs.orglett.2c01497

  日期：2022.6.3

  1,3-diols with arylhydrazines via acceptorless dehydrogenative coupling reactions to selectively synthesize pyrazoles and 2-pyrazolines were reported, which were based on Ru3(CO)12/NHC-phosphine-phosphine catalytic systems. The reactions featured low catalyst loading, high selectivity, wide substrate scope, and good yields, with only water and hydrogen gas (H2) as the byproducts.

  本文报道了基于Ru 3 (CO) 12 /NHC-膦-膦催化体系的1,3-二醇与芳基肼通过无受体脱氢偶联反应选择性合成吡唑和2-吡唑啉的不同转化。该反应具有催化剂负载量低、选择性高、底物范围广、收率高的特点，仅副产物水和氢气（H 2 ）。
• Aqueous N-Heterocyclization of Primary Amines and Hydrazines with Dihalides:  Microwave-Assisted Syntheses of <i>N</i>-Azacycloalkanes, Isoindole, Pyrazole, Pyrazolidine, and Phthalazine Derivatives
  作者：Yuhong Ju、Rajender S. Varma

  DOI：10.1021/jo051878h

  日期：2006.1.1

  The synthesis of nitrogen-containing heterocycles from alkyl dihalides (ditosylates) and primary amines and hydrazines via a simple and efficient cyclocondensation in an alkaline aqueous medium that occurs under microwave irradiation is described. This improved greener synthetic methodology provides a simple C C and straightforward one-pot approach to the synthesis of a variety of heterocycles, such as substituted azetidines, pyrrolidines, piperidines, azepanes, N-substituted 2,3-diliydro-1H-isoindoles. 4,5-dihydropyrazoles, pyrazolidines, and 1,2-dihydrophthalazines.
• Facile Synthesis of 1-Arylpyrazoles
  作者：Yiwen Yang、Chunxiang Kuang

  DOI：10.1055/s-0034-1380658

  日期：——

  A convenient and transition-metal-free synthesis of 1-arylpyrazoles that involves the cycloaddition of 3-arylsydnones and acrylic acid is presented. The process proceeds smoothly to obtain the target products with moderate to high yields.
• US9611230B2
  申请人：——

  公开号：US9611230B2

  公开（公告）日：2017-04-04