2-methyl-2-(4-nitrophenyl)-2,3-dihydro-1H-perimidine

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-methyl-2-(4-nitrophenyl)-2,3-dihydro-1H-perimidine
• 英文别名: 2-Methyl-2-(4-nitrophenyl)-1,3-dihydroperimidine
• 化学式: C₁₈H₁₅N₃O₂
• 分子量: 305.336
• InChiKey: YFHACZKGFLTUPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  69.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-methyl-2-(4-nitrophenyl)-2,3-dihydro-1H-perimidine 、 碘甲烷 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以83%的产率得到1,2-dimethyl-2-(4-nitrophenyl)-2,3-dihydro-1H-perimidine
  参考文献：
  名称：

  Visible light-sensitive properties of 1,2-dimethyl-2-(2-nitrophenyl)-2,3-dihydro-1H-perimidine

  摘要：

  Four o- and p-nitro substituted 2-methyl-2-phenyl-2,3-dihydro-1H-perimidine derivatives were synthesized via a condensation cyclization of naphthalene-1,8-diamine with nitro substituted acetophenones to study their photochemical properties. Only the o-nitrophenyl substituted perimidine 1 was found to be sensitive to light. When exposed to visible light under either aerobic conditions or argon atmosphere, it undergoes pyrimidine ring-opening/deoxygenation and pyrimidine oxidation to give the 2H-indazole 10 and perimidinone 11, respectively. A new visible light-sensitive o-nitrobenzylamino scaffold is introduced. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.01.079
• 作为产物：
  描述：

  对硝基苯乙酮 、 1,8-二氨基萘 在 chitosan hydrochloride 作用下， 以 水 为溶剂， 反应 0.6h， 以95%的产率得到2-methyl-2-(4-nitrophenyl)-2,3-dihydro-1H-perimidine
  参考文献：
  名称：

  壳聚糖盐酸盐介导的高效，绿色催化方法，用于合成perimidine衍生物

  摘要：

  壳聚糖盐酸盐是一种基于生物聚合物，可再生和可循环使用的异质催化剂，可用于高效一锅合成perimidine衍生物。这种新开发的绿色方法论为短时间内以优异的产率合成perimidines提供了一种非常简单且绿色的途径。

  DOI：

  10.1002/jhet.3700

文献信息

• Efficient Synthesis of 2,3-Dihydro-1H-Perimidine Derivatives Using HBOB as a Novel Solid Acid Catalyst
  作者：Sunanda B. Phadtare、R. Vijayraghavan、Ganapati S. Shankarling、Douglas R. MacFarlane

  DOI：10.1071/ch11381

  日期：——

  An efficient method for the synthesis of substituted 2,3-dihydro-1H-perimidine derivatives is described using bis(oxalato)boric acid (HBOB) as catalyst. The methodology provides an easily handled and recyclable catalyst for this type of reaction as an alternative platform to the conventional acid-catalyzed thermal processes. The time required to complete the reaction using HBOB was found to be shorter than conventional methods. Recycling of the catalyst has been efficiently achieved using a simple procedure.

  介绍了一种使用双（草酸）硼酸 (HBOB) 作为催化剂合成取代的 2,3- 二氢-1H-哌啶衍生物的高效方法。该方法为此类反应提供了一种易于处理且可回收的催化剂，可作为传统酸催化热工艺的替代平台。与传统方法相比，使用 HBOB 完成反应所需的时间更短。催化剂的回收利用也通过简单的程序有效实现。
• Squaric acid: an impressive organocatalyst for the synthesis of biologically relevant 2,3-dihydro-1H-perimidines in water
  作者：Sushil Khopkar、Ganapati Shankarling

  DOI：10.1007/s12039-019-1735-1

  日期：2020.12

  Abstract Squaric acid, a green, metal-free and eco-friendly organocatalyst, has been exploited for the synthesis of biologically interesting 2,3-dihydro-1H-perimidines. The reaction was performed using water as a green reaction medium and the organocatalyst can be easily recovered and reused up to four consecutive cycles without much decrease in catalytic activity. Several advantages of the present

  摘要 方酸是一种绿色，无金属，环境友好的有机催化剂，已被用于合成具有生物意义的2,3-二氢-1H-亚氨基吡啶。使用水作为绿色反应介质进行反应，并且有机催化剂可以容易地回收并重复使用多达四个连续循环，而催化活性没有很大降低。本方法的几个优点是催化剂用量低，催化剂性能优异，催化剂易于处理，反应条件温和，操作简便，产物易于分离，避免了色谱分离，在较短的反应时间内所需产物的收率高，原子经济性和基于二苯甲酮的perimidine的合成。 图形摘要 开发了一种无金属的方酸催化方法，用于在水中合成生物学上相关的2，3-二氢-1H-亚氨基吡啶。
• Chitosan hydrochloride mediated efficient, green catalysis for the synthesis of perimidine derivatives
  作者：Premchand B. Shelke、Suraj N. Mali、Hemchandra K. Chaudhari、Amit P. Pratap

  DOI：10.1002/jhet.3700

  日期：2019.11

  Chitosan hydrochloride as biopolymer‐based, renewable, and recyclable heterogeneous catalyst was used for efficient one‐pot synthesis of perimidine derivatives. This newly developed greener methodology provides a very simple and greener route for the synthesis of perimidines in short time with excellent yield.

  壳聚糖盐酸盐是一种基于生物聚合物，可再生和可循环使用的异质催化剂，可用于高效一锅合成perimidine衍生物。这种新开发的绿色方法论为短时间内以优异的产率合成perimidines提供了一种非常简单且绿色的途径。
• A metal free, eco-friendly protocol for the synthesis of 2,3-dihydro-1H-perimidines using commercially available Amberlyst 15 as a catalyst
  作者：Vilas Venunath Patil、Ganapati Subray Shankarling

  DOI：10.1016/j.catcom.2014.08.024

  日期：2014.12

  An efficient protocol has been developed to synthesize various dihydro-1H-perimidine derivatives using commercially available Amberlyst-15 as a catalyst. Dihydro-1H-perimidine derivatives are potential candidates for pharmaceutical and high tech applications. The conspicuous features of this protocol are short reaction time, compared to higher product yield, easy recovery, reusability and regeneration of catalyst. The reaction was successfully scaled up to gram level, which reflects the practicability of the present protocol. (C) 2014 Elsevier B.V. All rights reserved.
• Bismuth(III) Chloride–Promoted Efficient Synthesis of Perimidine Derivatives under Ambient Conditions
  作者：Junmin Zhang、Songlin Zhang

  DOI：10.1080/00397910701463011

  日期：2007.8