2,6-dichloro-N'-phenylbenzohydrazonoyl chloride | 39719-44-3

• 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: 2,6-dichloro-N'-phenylbenzohydrazonoyl chloride
• 英文别名: 2,6-Dichlorbenzoylchloridphenylhydrazon；2,6-dichlorobenzoyl chloride phenylhydrazone；2,6-dichloro-N-phenylbenzenecarbohydrazonoyl chloride
• CAS: 39719-44-3
• 化学式: C₁₃H₉Cl₃N₂
• 分子量: 299.587
• InChiKey: IWXWPUUEOMUWJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  18
• 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：
  24.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl 4-methylene-5-oxohexanoate 、 2,6-dichloro-N'-phenylbenzohydrazonoyl chloride 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以76%的产率得到ethyl 3-[3-acetyl-5-(2,6-dichlorophenyl)-2-phenyl-4H-pyrazol-3-yl]propanoate
  参考文献：
  名称：

  通过分子内环化/甲基化合成一锅螺吡唑啉

  摘要：

  在一个反应​​容器中，通过官能化 5,5-二取代吡唑啉的串联分子内环化/甲基化反应合成区域异构体螺吡唑啉。5,5-吡唑啉是通过含有腈亚胺的芳香环和双取代的孪生烯烃的1,3-偶极环加成反应构建的。对吡唑啉上亲核和亲电官能团的相对位置进行了评估，以确定用于分子内环化/甲基化反应的最佳吡唑啉系统。与具有直接键合的酯的吡唑啉相比，具有离吡唑啉更远的亲电酯的吡唑啉实现了更高的螺吡唑啉分离产率。

  DOI：

  10.1016/j.tetlet.2011.03.004
• 作为产物：
  描述：

  2,6-dichlorobenzaldehyde phenylhydrazone 在 N-氯代丁二酰亚胺 、 二甲基硫 作用下， 以 二氯甲烷 为溶剂， 生成 2,6-dichloro-N'-phenylbenzohydrazonoyl chloride
  参考文献：
  名称：

  新型螺-萘-1.2'- [1,3,4]恶二唑-4-ones 的结构评估在分批和流动化学下制备，具有简明的抗真菌和抗（真菌）细菌活性

  摘要：

  肼酰氯与 2,3-二氯-1,4-萘醌的反应在分批和流动合成方法下产生了药学上重要的螺-萘-1,2'-[1,3,4]恶二唑-4-酮。区域选择性环加成方案在温和条件下运行，可耐受多种结构部分，并高效提供多功能螺恶二唑基序。所得产物经IR、1 H NMR、13 C NMR、HRMS和化合物6h鉴定采用单晶 X 射线衍射技术对其进行了表征。合成的分子在 DFT/B3LYP/def2-TVZP 水平上通过量子化学计算进行了理论分析，为实验结果提供了支持数据。此外，还报道了一些选定的新型螺环分子的简明生物学评价。

  DOI：

  10.1016/j.tet.2022.133231

文献信息

• Asymmetric Catalytic 1,3-Dipolar Cycloaddition Reaction of Nitrile Imines for the Synthesis of Chiral Spiro-Pyrazoline-Oxindoles
  作者：Gang Wang、Xiaohua Liu、Tianyu Huang、Yulong Kuang、Lili Lin、Xiaoming Feng

  DOI：10.1021/ol303097j

  日期：2013.1.4

  cycloaddition of nitrile imines with 3-alkenyl-oxindoles was catalyzed by a new chiral Mg(ClO4)2 complex of an N,N′-dioxide ligand. The reaction is so far the sole catalytic synthesis of spiro-pyrazoline-oxindole derivatives. A wide variety of substrates were explored to obtain good yields (up to 98%) and excellent enantioselectivities (up to 99%). This cycloaddition expands the scope of propargyl anion type 1

  新型的N，N'-二氧化物配体的手性Mg（ClO 4）2配合物催化了腈亚胺与3-烯基-氧吲哚的新的1,3-偶极环加成反应。到目前为止，该反应是螺-吡唑啉-羟吲哚衍生物的唯一催化合成。探索了多种底物以获得良好的产率（高达98％）和优异的对映选择性（高达99％）。这种环加成反应扩大了2-吡唑啉亚基结构中1，3-偶极炔丙基阴离子的范围。
• Anthelmintic methods employing benzoyl chloride phenylhydrazones
  申请人：The Upjohn Company

  公开号：US03932661A1

  公开（公告）日：1976-01-13

  Certain benzoyl chloride phenylhydrazones have been found to be active against insects and mites, and they have also been found to be effective, broad-spectrum anthelmintics for suppressing parasitic worms in animals, particularly sheep. The benzoyl ring and the phenylhydrazone ring can be substituted with a halogen atom, a nitro group, or an alkyl group of from 1 to 6 carbon atoms, inclusive. A new class of pentahalobenzoyl chloride phenylhydrazones is described, particularly pentafluorobenzoyl chloride phenylhydrazones. The compounds are prepared by reacting a benzoic acid phenylhydrazide with phosphorus pentachloride to obtain a benzoyl chloride (dichlorophosphinyl)phenylhydrazone that is reacted with phenol to produce the desired benzoyl chloride phenylhydrazones. Certain of the compounds can be prepared by direct chlorination of a benzaldehyde phenylhydrazone. Methods of using the new compounds and new anthelmintic formulations are described. The new compound p-toluoyl chloride phenylhydrazone is effective against worms at rates at least as low as 100 mg./kg. of body weight in sheep.

  某些苯甲酰氯苯基肼已被发现对昆虫和螨具有活性，它们还被发现对动物，特别是羊体内的寄生虫蠕虫有抑制作用，是有效的广谱驱虫剂。苯甲酰环和苯基肼环可以被卤素原子、硝基团或含有1至6个碳原子的烷基取代。描述了一类新的五卤苯甲酰氯苯基肼，特别是五氟苯甲酰氯苯基肼。通过将苯甲酸苯基肼与五氯化磷反应以获得苯甲酰氯（二氯磷基）苯基肼，然后将其与酚反应以产生所需的苯甲酰氯苯基肼来制备这些化合物。其中的一些化合物可以通过对苯甲醛苯基肼进行直接氯化制备。描述了使用新化合物和新驱虫剂配方的方法。新化合物对羊体重至少为100毫克/千克的剂量具有对抗蠕虫的有效性。
• Synthesis of fully substituted pyrazoles from pyridinium 1,4-zwitterionic thiolates and hydrazonoyl chlorides <i>via</i> a [[3 + 3] − 1] pathway
  作者：Bin Cheng、Bian Bao、Wei Xu、Yuntong Li、Hui Li、Xinping Zhang、Yun Li、Taimin Wang、Hongbin Zhai

  DOI：10.1039/d0ob00224k

  日期：——

  practical protocol for the synthesis of fully substituted pyrazoles from pyridinium 1,4-zwitterionic thiolates and hydrazonoyl chlorides in excellent yields under mild conditions is described. The transformation proceeds via an unusual [[3 + 3] - 1] pathway, which involves a formal [3 + 3] cascade cyclization followed by a spontaneous ring-contraction/sulfur extrusion reaction from 4H-1,3,4-thiadiazine intermediates

  描述了一种新颖实用的方案，可在温和的条件下以极佳的收率由吡啶鎓1,4-两性离子硫醇盐和酰氯合成全取代的吡唑。转化是通过不寻常的[[3 + 3]-1]途径进行的，该途径涉及正式的[3 + 3]级联环化，然后由4H-1,3,4-噻二嗪中间体进行自发的环收缩/硫磺挤出反应。
• Method of use, composition, and compounds
  申请人：The Upjohn Company

  公开号：US04017540A1

  公开（公告）日：1977-04-12

  Certain benzoyl chloride phenylhydrazones have been found to be active against insects and mites. The benzoyl ring and the phenylhydrazone ring can be substituted with a halogen atom, a nitro group, or an alkyl group of from 1 to 6 carbon atoms, inclusive. A new class of pentahalobenzoyl chloride phenylhydrazones is described, particularly pentafluorobenzoyl chloride phenylhydrazones. A further new class of alkylbenzoyl chloride phenylhydrazones, particularly p-toluoyl chloride phenylhydrazones are also described. The compounds are prepared by reacting a benzoic acid phenylhydrazide with phosphorus pentachloride to obtain a benzoyl chloride (dichlorophosphinyl)phenylhydrazone that is reacted with phenol to produce the desired benzoyl chloride phenylhydrazones. Certain of the compounds can be prepared by direct chlorination of a benzaldehyde phenylhydrazone. Methods of use and compositions are described.

  某些苯甲酰氯苯肼已被发现对昆虫和螨类具有活性。苯甲酰环和苯肼酮环可被卤素原子、硝基团或含有1至6个碳原子的烷基取代。描述了一种新类五卤苯甲酰氯苯肼，特别是五氟苯甲酰氯苯肼。还描述了一种新类烷基苯甲酰氯苯肼，特别是对甲酰氯苯肼。这些化合物通过将苯甲酸苯肼与五氯化磷反应制备苯甲酰氯（二氯磷基）苯肼，然后与酚反应制备所需的苯甲酰氯苯肼。其中一些化合物可通过对苯甲醛苯肼直接进行氯化制备。描述了使用方法和组成物。
• A novel synthesis of 1,3,5-trisubstituted pyrazoles through a spiro-pyrazoline intermediate via a tandem 1,3-dipolar cycloaddition/elimination
  作者：Sureshbabu Dadiboyena、Edward J. Valente、Ashton T. Hamme

  DOI：10.1016/j.tetlet.2008.10.145

  日期：2009.1

  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.