3-nitro-N-phenylbenzohydrazonoyl chloride | 63614-84-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-nitro-N-phenylbenzohydrazonoyl chloride
• 英文别名: 3-nitro-N'-phenyl-benzohydrazonoyl chloride；3-nitro-N-phenylbenzenecarbohydrazonoyl chloride
• CAS: 63614-84-6
• 化学式: C₁₃H₁₀ClN₃O₂
• 分子量: 275.694
• InChiKey: MJGJTLYYHKYFIX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  70.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-nitro-N-phenylbenzohydrazonoyl chloride 、 ethyl 2-azido-3-phenylacrylate 在 caesium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以36%的产率得到3-(3-nitrophenyl)-1,4-diphenyl-1H-pyrazole-5-carboxylic acid ethyl ester
  参考文献：
  名称：

  A facile approach to polysubstituted pyrazoles from hydrazonyl chlorides and vinyl azides

  摘要：

  A novel and facile approach to polysubstituted pyrazoles from readily synthesized hydrazonyl chlorides and vinyl azides was developed. The reaction was regiospecific and proceeded under mild conditions in the presence of base. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.04.103
• 作为产物：
  描述：

  1-(3-nitrobenzylidene)-2-phenylhydrazine 在 N-氯代丁二酰亚胺 、 二甲基硫 作用下， 以 二氯甲烷 为溶剂， 以52%的产率得到3-nitro-N-phenylbenzohydrazonoyl chloride
  参考文献：
  名称：

  A novel synthesis of 1,3,5-trisubstituted pyrazoles through a spiro-pyrazoline intermediate via a tandem 1,3-dipolar cycloaddition/elimination

  摘要：

  The syntheses of an important class of hitherto unreported 1,3,5-pyrazoles, inspired by all unanticipated eliminatory ring opening are described, The reported pyrazole compounds were constructed through the Huisgen cyclization of 2-methylene-1,3,3-trimethylindoline and an in situ generated nitrile imine. The newly formed spiro-pyrazoline intermediate presumably then undergoes a ring opening/elimination process to afford a pyrazole, as evidenced by single X-ray crystal data. The Current report constitutes the first formal observation of this kind of ring opening involving a spiro-pyrazoline intermediate. Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2008.10.145

文献信息

• Stereoconvergent and stepwise 1,3-dipolar cycloadditions of nitrile oxides and nitrile imines
  作者：Zhenni Zhao、Zhi Ou、Subarna Jyoti Kalita、Feng Cheng、Qian Huang、Yangyi Gu、Yuhao Wang、Yan Zhao、Yiyong Huang

  DOI：10.1016/j.cclet.2021.12.006

  日期：2022.6

  stereoconvergent 1,3-dipolar cycloaddition of nitrile oxides and nitrile imines with E/Z isomeric mixture of electron-deficient olefins is reported, delivering isoxazolines and pyrazolines bearing two vicinal stereogenic tertiary and trifluoromethylated quaternary carbon centers with perfect regio- and diastereoselectivities. The possibility of concerted cycloaddition/epimerization sequence under basic

  报道了腈氧化物和腈亚胺与缺电子烯烃的E / Z异构体混合物的立体收敛 1,3-偶极环加成的第一个例子，提供了带有两个邻位立体叔和三氟甲基化季碳中心的异恶唑啉和吡唑啉，具有完美的区域和非对映选择性。通过一些对照实验和DFT计算，排除了在碱性条件下协同环加成/差向异构序列形成热力学稳定的非对映异构体的可能性，并提出了逐步机理。
• 1,3-Dipolar [3 + 3] cycloaddition of α-halohydroxamate-based azaoxyallyl cations with hydrazonoyl chloride-derived nitrile imines
  作者：Hong-Wu Zhao、Yu-Di Zhao、Yue-Yang Liu、Li-Jiao Zhao、Xiu-Qing Song、Xiao-Qin Chen、Hai-Liang Pang、Juan Du、Ning-Ning Feng

  DOI：10.1039/c7ra09766b

  日期：——

  Promoted by Et3N, the 1,3-dipolar [3 + 3] cycloaddition of α-halohydroxamate-based azaoxyallylcations with hydrazonoyl chloride-derived nitrile imines occurred efficiently, and furnished desired products in acceptable chemical yields. The chemical structure of the title compounds was firmly confirmed by an X-ray single crystal structure analysis.

  在Et 3 N的促进下，α-卤代异羟肟酸酯基的氮杂烯丙基烯丙基化反应与酰肼基氯衍生的腈亚胺的1,3-偶极[3 + 3]环加成反应得以有效地进行，并以可接受的化学产率提供了所需的产物。通过X射线单晶结构分析牢固地确认了标题化合物的化学结构。
• Construction of multi-substituted pyrazoles <i>via</i> potassium carbonate-mediated [3 + 2] cycloaddition of <i>in situ</i> generated nitrile imines with cinnamic aldehydes
  作者：Mei-Mei Li、Hui Huang、Wanrong Tian、Yiru Pu、Chaozheng Zhang、Jirui Yang、Qing Ren、Feiyan Tao、Yun Deng、Jun Lu

  DOI：10.1039/d2ra00331g

  日期：——

  A highly efficient potassium carbonate-mediated [3 + 2] cycloaddition reaction of hydrazonoyl chlorides with cinnamic aldehydes to furnish multi-substituted pyrazoles under nontoxic and mild conditions has been developed.

  一种高效的无毒和温和条件下，利用碳酸钾介导的氮酰氯与肉桂醛[3 + 2]环加成反应，生成多取代的吡唑烷化合物的方法已经被开发出来。
• Synthesis of novel isoxazole-containing pyrazolines and pyrazoles via cycloaddition and elimination/aromatization process
  作者：Hui Huang、Yiru Pu、Dikai Zhu、Chaozheng Zhang、Jirui Yang、Changqun Liu、Xin Zhang、Feiyan Tao、Mei-Mei Li、Jun Lu

  DOI：10.1016/j.tet.2022.133203

  日期：2023.1

  approach for synthesizing isoxazole-containing pyrazolines and pyrazoles. The protocol involved [3 + 2] cycloaddition of the in situ generated nitrile imines with 3-methyl-4-nitro-5-alkenyl isoxazoles furnishing a sequence of trans-configured isoxazole-substituted pyrazolines in a fully regioselective manner. Elimination/aromatization of the prepared cycloadducts with the catalysis of MnO2 or SnCl2 provided

  我们提出了合成含异恶唑的吡唑啉和吡唑的一般方法。该方案涉及原位生成的腈亚胺与 3-甲基-4-硝基-5-烯基异恶唑的 [3 + 2] 环加成，以完全区域选择性的方式提供一系列反式配置的异恶唑取代的吡唑啉。在 MnO 2或 SnCl 2的催化作用下，制备的环加合物的消除/芳构化提供了获得多取代吡唑的简便途径。通过控制催化剂，芳构化过程产生异恶唑取代的吡唑 (MnO 2 ) 或 1,3,4-三芳基吡唑 (SnCl 2) 具有优异的选择性。此外，该方法允许通过一锅法合成异恶唑取代的吡唑。
• 一种多取代吡唑啉类化合物及其合成方法
  申请人：四川普康药业有限公司

  公开号：CN115536649A

  公开（公告）日：2022-12-30

  本发明提供一种多取代吡唑啉类化合物及其合成方法，主要涉及吡唑啉类化合物技术领域，在有机溶剂中，室温下加入底物腙、乙烯基异恶唑和碱反应完全后，经过分离提纯，得到一种稠环1,3,4,5‑四取代吡唑啉类化合物。发明设计科学，构思巧妙，方法简单，操作简便，采用本发明方法能特异得合成一种全新的多种取代基的吡唑啉类化合物，且较之传统方法副产物少，易于纯化，产率极高。解决了已知生产方法中合成此类吡唑啉类化合物的限制，证了此方法的实用性。