2-(4-chlorophenyl)-1H-perimidine | 28478-19-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类 - 二氮杂萘
• 英文名称: 2-(4-chlorophenyl)-1H-perimidine
• CAS: 28478-19-5
• 化学式: C₁₇H₁₁ClN₂
• mdl: MFCD01329957
• 分子量: 278.741
• InChiKey: PYNMVASVFWXKSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• 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：
  1

反应信息

• 作为反应物：
  描述：

  2-(4-chlorophenyl)-1H-perimidine 在 甲烷磺酸 作用下， 以 neat (no solvent) 为溶剂， 反应 0.08h， 生成 7-bromo-2-(4-chlorophenyl)benzo[gh]perimidine
  参考文献：
  名称：

  7-溴-1,3-二氮杂戊烯的合成

  摘要：

  以前无法获得的7-溴-1,3-二氮杂戊烯类可以通过容易获得的7-（5-溴-3,4-二氢嘧啶-4-基）-1H-嘧啶的熔体周环合成来合成。

  DOI：

  10.1002/ejoc.201800703
• 作为产物：
  描述：

  4-氯苯甲醛 、 1,8-二氨基萘 在 sodium metabisulfite 作用下， 以 乙醇 为溶剂， 反应 8.0h， 以90%的产率得到2-(4-chlorophenyl)-1H-perimidine
  参考文献：
  名称：

  An Improved One-Pot Method for the Preparation of 2-Substituted 1H-Perimidines

  摘要：

  2-substituted H-1-perimidines are readily prepared, in high yields, by refluxing a mixture of sodium pyrosulfite, an aldehyde, and 1,8-diaminonaphthalene in aqueous ethanol or N,N-dimethylformamide. The method is of wide applicability except from araldehydes bearing a strong electron-withdrawing group (-CN, -NO2).

  DOI：

  10.1080/00397919108055450

文献信息

• A Cobalt Catalyst Permits the Direct Hydrogenative Synthesis of 1 <i>H</i> ‐Perimidines from a Dinitroarene and an Aldehyde
  作者：Tobias Schwob、Mirco Ade、Rhett Kempe

  DOI：10.1002/cssc.201900498

  日期：2019.7.5

  A new sustainable catalytic reaction, the synthesis of 1H‐ perimidines from a dinitroarene and an aldehyde in the presence of H2, was achieved. An earth‐abundant metal catalyst was developed to permit the efficient, highly chemoselective, and consecutive hydrogenation of dinitroarenes. The catalyst was reusable and easy to handle. The use of a specific Co complex and its pyrolysis at a certain temperature

  实现了一种新的可持续催化反应，即在H 2存在下由二硝基芳烃和醛合成1 H-亚氨基吡啶。开发了一种富含地球的金属催化剂，可实现对二硝基芳烃的高效，高度化学选择性和连续氢化。该催化剂是可重复使用的并且易于处理。使用特定的Co配合物及其在一定温度下的热解对于实现有机物转化的高活性至关重要。苯甲醛和脂肪醛可能会发生加氢缩合反应，因此可以容忍许多官能团，包括对碘敏感的芳基，腈基，烯烃和炔基等加氢敏感的例子。
• Synthesis of 2-aryl-1<i>H</i>-Benzimidazoles and 2-aryl-1<i>H</i>-perimidines Using Arylidene Meldrum's Acid as a Source of the Aryl Group and Oxidant
  作者：Hossein Mehrabi、Faezeh Najafian-Ashrafi、Zeinab Esfandiarpour、Reza Ranjbar-Karimi

  DOI：10.3184/174751918x15199196317528

  日期：2018.3

  Arylidene Meldrum's acid is employed as a source of the aryl group and oxidant for the synthesis of 2-aryl-1H–benzimidazoles by a condensation reaction with 1,2-phenylenediamine in refluxing ethanol with good to high yields. Arylidene Meldrum's acids were also used as a source of the aryl group and oxidant for the synthesis of 2-aryl-1H-perimidines by a condensation reaction with 1,8-diaminonaphthalene

  亚芳基 Meldrum 酸被用作芳基的来源和氧化剂，用于通过与 1,2-苯二胺在回流乙醇中的缩合反应合成 2-芳基-1H-苯并咪唑，收率良好至高。亚芳基 Meldrum 的酸也被用作芳基的来源和氧化剂，用于通过与 1,8-二氨基萘在回流乙醇中的缩合反应以高产率合成 2-芳基-1H-脒。
• Rational design of an efficient one-pot synthesis of 6H-pyrrolo[2,3,4-gh]perimidines in polyphosphoric acid
  作者：Alexander V. Aksenov、Nicolai A. Aksenov、Dmitrii S. Ovcharov、Dmitrii A. Aksenov、Georgii Griaznov、Leonid G. Voskressensky、Michael Rubin

  DOI：10.1039/c6ra17269e

  日期：——

  Several highly efficient one-pot synthetic protocols were developed, enabling polyphosphoric acid-activated nitroalkanes to act as electrophiles in reactions with aminonapthalenes. The featured methods allow for the single step assembly of...

  开发了几种高效的一锅法合成方案，使多磷酸活化的硝基烷烃在与氨基萘的反应中充当亲电试剂。特色方法允许单步组装...
• Pyrimidines as Surrogates for 1,3-Dicarbonyl Compounds in<i>peri</i>Annulation of Perimidines en Route to 1,3-Diazapyrenes
  作者：Alexander V. Aksenov、Stanisvlav V. Shcherbakov、Irina V. Lobach、Inna V. Aksenova、Michael Rubin

  DOI：10.1002/ejoc.201601589

  日期：2017.3.27

  A highly efficient protocol for acid-mediated peri-annulation of perimidines with pyrimidines was developed. Pyrimidines, used as surrogates for 1,3-dicarbonyl compounds allow for furnishing benzo[gh]perimidines, including hardly available analogs, non-substituted, or mono-substituted at C-6, C-8. Limitations of reactions employing 5-bromopyrimidines are investigated.

  开发了一种用于酸介导的嘧啶环化环化的高效方案。用作 1,3-二羰基化合物替代物的嘧啶允许提供苯并[gh] 嘧啶，包括几乎无法获得的类似物、未取代的或在 C-6、C-8 处单取代的类似物。研究了使用 5-溴嘧啶的反应的局限性。
• Application of Bertagnini's Salts in a Mechanochemical Approach Toward Aza‐Heterocycles and Reductive Aminations via Imine Formation
  作者：Sourav Behera、Shyamal Kanti Bera、Francesco Basoccu、Federico Cuccu、Pietro Caboni、Lidia De Luca、Andrea Porcheddu

  DOI：10.1002/adsc.202301407

  日期：——

  with solid reagents. We have showcased the practicality of Bertagnini's salts, also called aldehyde-bisulfite adducts, which are crystalline, simplifying preparation and storage. These salts are stable substitutes for liquid aldehydes and ketones that have been effectively employed in reductive amination, synthesizing aza-heterocycles and hydrazones within mechanochemistry. The technique's effectiveness

  我们的研究表明，使用固体试剂进行机械化学活化更有效。我们展示了贝尔塔尼尼盐（也称为醛-亚硫酸氢盐加合物）的实用性，它们是结晶，简化了制备和储存。这些盐是液体醛和酮的稳定替代品，可有效用于机械化学中的还原胺化、氮杂杂环和腙的合成。该技术的有效性拓宽了底物范围，简化了纯化，减少了反应时间，并提供了良好的产物收率。此外，亚硫酸氢盐加合物的热稳定性已通过 TGA（热重分析）分析得到证实。