ethyl 1,3-diphenyl-1H-pyrazole-4-carboxylate | 7189-03-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 1,3-diphenyl-1H-pyrazole-4-carboxylate
• 英文别名: ethyl1,3-diphenyl-1H-pyrazole-4-carboxylate；1,3-diphenyl-1H-pyrazole-4-carboxylic acid ethyl ester；1,3-Diphenyl-pyrazolcarbonsaeure-(4)-ethylester；ethyl 1,3-diphenylpyrazole-4-carboxylate
• CAS: 7189-03-9
• 化学式: C₁₈H₁₆N₂O₂
• 分子量: 292.337
• InChiKey: UWEPGNDDAIRWGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  在 盐酸 作用下， 以 乙醇 为溶剂， 生成 ethyl 1,3-diphenyl-1H-pyrazole-4-carboxylate
  参考文献：
  名称：

  [EN] PROCESS FOR THE REGIOSELECTIVE SYNTHESIS OF PYRAZOLES
  [FR] PROCÉDÉ DE SYNTHÈSE RÉGIOSÉLECTIVE DES PYRAZOLES

  摘要：

  描述了一种合成具有通式(I)的吡唑的过程，包括以下步骤：混合具有通式(II)的化合物和具有通式(III)的1,2-二取代肼，形成具有通式(IV)的反应中间体，以及在酸性环境中，步骤i)得到的反应混合物环化生成具有通式(I)的吡唑，反应方案1如下。

  公开号：

  WO2015097658A1

文献信息

• Application of Photoclick Chemistry for the Synthesis of Pyrazoles via 1,3-Dipolar Cycloaddition between Alkynes and Nitrilimines Generated In Situ
  作者：Richard Remy、Christian G. Bochet

  DOI：10.1002/ejoc.201701225

  日期：2018.1.23

  The photolysis of tetrazoles leads to the extrusion of dinitrogen and forms a reactive nitrile imine intermediate. The latter can then react in situ with alkynes in a [3+2] cycloaddition providing pyrazoles. Some reactivity trends were identified, such as a preference for electron‐poor alkynes. On the tetrazole part, there is a clear preference for either aromatic or conjugated substituents.

  四唑的光解导致二氮的挤出并形成反应性腈亚胺中间体。然后后者可以在[3 + 2]环加成反应中与炔烃原位反应，提供吡唑。确定了一些反应性趋势，例如偏爱电子贫乏的炔烃。在四唑部分，显然优选芳族或共轭取代基。
• Diastereoselective Synthesis of Pyrazolines using a Bifunctional Brønsted Acidic Ionic Liquid under Solvent-Free Conditions
  作者：Shirin Safaei、Iraj Mohammadpoor-Baltork、Ahmad R. Khosropour、Majid Moghadam、Shahram Tangestaninejad、Valiollah Mirkhani

  DOI：10.1002/adsc.201200191

  日期：2012.11.12

  An efficient protocol for the excellent diastereoselective synthesis of pyrazolines via a three-component reaction of aldehydes, hydrazines and dimethyl acetylenedicarboxylate (DMAD) in the presence of a bifunctional Brønsted acidic ionic liquid as a reusable catalyst under solvent-free conditions is reported. Easy work-up, short reaction times, high yields of the products and an environmentally benign

  为吡唑啉的非对映选择性优良的合成高效的协议经由报道醛类，肼类的在双官能性布朗斯台德酸性离子液体的存在，作为无溶剂的条件下，可重复使用的催化剂的三组分反应和乙炔二（DMAD）。该方法的其他显着特点是易于后处理，反应时间短，产物的产率高以及避免有毒有机溶剂的环境友好程序。
• One-Pot Synthesis of Functionalized 3-Aryl-1-phenyl-1<i>H</i>-pyrazoles from Hydrazonoyl Chlorides and Acetylenic Esters in the Presence of Ph₃P
  作者：Issa Yavari、Gholamhossein Khalili、Anvar Mirzaei

  DOI：10.1002/hlca.200900246

  日期：2010.2

  The zwitterionic 1 : 1 intermediates generated by addition of Ph3P to acetylenic esters is trapped by 1‐[(aryl)chloromethylene]‐2‐phenylhydrazines (=N‐phenylarenecarbohydrazonoyl chlorides) to yield functionalized 3‐aryl‐1‐phenyl‐1H‐pyrazoles in good yields.

  将Ph 3 P加到炔属酯中生成的两性离子1：1中间体被1-[（（芳基）氯亚甲基] -2-苯基肼（= N-苯基芳基碳酰肼基氯）捕获）生成官能化的3-芳基-1-苯基-1 H-吡唑类化合物的收率很高。
• Copper-Promoted Aerobic Oxidative [3+2] Cycloaddition Reactions of N,N-Disubstituted Hydrazines with Alkynoates: Access to Substituted Pyrazoles
  作者：Xiaoying Zou、Lvyin Zheng、Xiaoya Zhuo、Yumei Zhong、Yingying Wu、Beining Yang、Qifang He、Wei Guo

  DOI：10.1021/acs.joc.2c02610

  日期：2023.2.17

  A copper-promoted aerobic oxidative [3+2] cycloaddition reaction for the synthesis of various substituted pyrazoles from N,N-disubstituted hydrazines with alkynoates in the presence of bases is developed. This work involves a direct C(sp3)–H functionalization and the formation of new C–C/C–N bonds. In this strategy, inexpensive and easily available Cu2O serves as the promoter and air acts as the green

  开发了铜促进的有氧氧化 [3+2] 环加成反应，用于在碱存在下从 N,N-二取代肼与炔酸酯合成各种取代吡唑。这项工作涉及直接 C(sp 3 )–H 功能化和新 C–C/C–N 键的形成。在该策略中，廉价易得的Cu 2 O作为促进剂，空气作为绿色氧化剂。该反应具有原子和步骤经济性高、区域选择性高、操作简单等优点。
• Fluorescent compounds for imaging of blood vessels and blood flow, and an in vivo screen for pro- and anti-angiogenic agents
  申请人：Mendoza Jose

  公开号：US10744213B2

  公开（公告）日：2020-08-18

  The present invention discloses fluorescent compounds and a method for their use for selective imaging of blood vessels and blood flow. By applying these fluorescent compounds and the imaging process to a zebrafish model, the present invention further provides methods and procedures for the discovery, selection, and characterization of pro- and anti-angiogenic agents.

  本发明公开了荧光化合物及其用于血管和血流选择性成像的方法。 通过将这些荧光化合物和成像过程应用于斑马鱼模型，本发明进一步提供了发现、选择和表征促血管生成剂和抗血管生成剂的方法和程序。