(2,6-dimethylpyridine-3,5-diyl)bis(phenylmethanone) | 24234-60-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2,6-dimethylpyridine-3,5-diyl)bis(phenylmethanone)
• 英文别名: 3,5-dibenzoyl-2,6-dimethyl pyridine；3,5-dibenzoyl-2,6-dimethylpyridine；3,5-dibenzoyl-2,6-dimethyl-pyridine；2,6-Dimethyl-3,5-dibenzoyl-pyridin；(5-benzoyl-2,6-dimethylpyridin-3-yl)-phenylmethanone
• CAS: 24234-60-4
• 化学式: C₂₁H₁₇NO₂
• 分子量: 315.371
• InChiKey: ADHDLDUKQXDATR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  47
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2,6-dimethylpyridine-3,5-diyl)bis(phenylmethanone) 在 sodium hydroxide 作用下， 以 乙醇 、 水 、 1,2-二氯乙烷 为溶剂， 生成 3,4-dibenzoyl-N,5-dimethylaniline
  参考文献：
  名称：

  Synthesis of Substituted 1H-Indazoles by Pyrazole Annelation to an Arene

  摘要：

  Substituted 1H-indazoles have been synthesized by reductive intramolecular heterocyclization of 2,4-di-aroyl-N-nitrosomethylanilines and 2,4-diacetyl-N-nitrosomethylaniline. The N-nitrosoanilines were obtained by nitrosation of N-methyl-2,4-diaroyl- and 2,4-diacetylanilines, the products of quaternary 3,5-diaroyl- and 3,5-diacetylpyridinium salt recyclization.

  DOI：

  10.1007/s10593-013-1244-y
• 作为产物：
  描述：

  3,5-dibenzoyl-2,6-dimethyl-1,4-dihydropyridine 在 四氯苯醌 作用下， 以 苯 为溶剂， 反应 2.0h， 以87%的产率得到(2,6-dimethylpyridine-3,5-diyl)bis(phenylmethanone)
  参考文献：
  名称：

  Synthesis of 3,5-diaroylpyridines

  摘要：

  Previously unknown 3,5-diaroylpyridines have been synthesized by the condensation of 1,3-diketones according to the Hantzsch reaction.

  DOI：

  10.1007/s10593-011-0784-2

文献信息

• One-Pot Synthesis of Hantzsch Pyridines<i>via</i>NH₄I Promoted Condensation of 1,3-Dicarbonyl Compounds with DMSO and NH₄OAc
  作者：Liming Chang、Junyi Lai、Gaoqing Yuan

  DOI：10.1002/cjoc.201600255

  日期：2016.9

  A one‐pot synthesis of Hantzsch pyridines was achieved through NH4I‐promoted condensation of 1,3‐dicarbonyl compounds with DMSO and NH4OAc, in which the C4 of the pyridine rings was derived from DMSO and the nitrogen atom resulted from NH4OAc and NH4I. The target product could be obtained in moderate to excellent yields.

  通过NH 4 I促进1,3-二羰基化合物与DMSO和NH 4 OAc的缩合反应实现Hantzsch吡啶的一锅合成，其中吡啶环的C4来自DMSO，氮原子来自NH 4 OAC和NH 4 I的目标产物可在温和获得到优异的产率。
• A metal-free strategy for the cross-dehydrogenative coupling of 1,3-dicarbonyl compounds with 2-methoxyethanol
  作者：Vishal Suresh Kudale、Sheng Zheng、Sheng-Hua Huang、Yu-Lun Chang、Jeh-Jeng Wang

  DOI：10.1039/d1ob02290c

  日期：——

  we report a metal-free approach for the construction of methylene-bridged bis-1,3-dicarbonyl compounds via cross-dehydrogenative coupling of 1,3-dicarbonyl compounds with 2-methoxyethanol. In addition, we have extended this methodology to synthesize tetra-substituted pyridine derivatives using 1,3-dicarbonyl, 2-methoxyethanol and NH4OAc in one step. The key advantages include accepting a wide range

  在这里，我们报告了一种通过1,3-二羰基化合物与 2-甲氧基乙醇的交叉脱氢偶联来构建亚甲基桥连双 1,3-二羰基化合物的无金属方法。此外，我们扩展了这一方法，以一步合成四取代吡啶衍生物，使用 1,3-二羰基、2-甲氧基乙醇和 NH 4 OAc。主要优势包括接受广泛的底物，利用 O 2作为唯一氧化剂，以及合成生物活性化合物，如 1,4-二氢吡啶和吡唑。
• Benzannulation and <i>N</i> ‐Annulation of β‐Ketoenamines for Synthesizing Aniline and Pyridine Derivatives Using DMSO as a Methine Source
  作者：Pallaba Ganjan Dalai、Niranjan Panda

  DOI：10.1002/adsc.202200886

  日期：2022.11.8

  N-annulation of β-ketoenamines by the in-situ generated methyl(methylene)sulfonium ion from the reaction of dimethyl sulfoxide (DMSO) and 1,2-dibromoethane (DBE) was achieved. The β-ketoenamines underwent N-annulation to pyridine derivatives, while the N-alkylated enamines were benzannulated to afford substituted anilines. The utility of the intermediate methyl(methylene)sulfonium ion was further extended for

  通过二甲基亚砜（DMSO）和1,2-二溴乙烷（DBE）的反应原位产生的甲基（亚甲基）锍离子实现了β-酮烯胺的苯环化和N-环化。β-酮烯胺经 N-环化生成吡啶衍生物，而N-烷基化烯胺经苯环化生成取代的苯胺。中间体甲基（亚甲基）锍离子的用途进一步扩展用于合成亚甲基桥联双-1,3-二羰基化合物。
• Rongalite as C1 Synthon in the Synthesis of Divergent Pyridines and Quinolines
  作者：Huan Gao、Liyun Zhou、Jie-Ping Wan、Yunyun Liu

  DOI：10.1021/acs.joc.3c00428

  日期：2023.6.2

  Rongalite has been used as a cheap and efficient carbon synthon for the synthesis of divergent N-heteroaromatics, including different pyridines and quinolines. The selective synthesis of different products can be achieved by employing enaminones or enaminones/anilines as reaction partners. In addition, compared with the reaction using conventional aldehyde synthons, rongalite displays an evident advantage

  Rongalite 已被用作一种廉价且高效的碳合成子，用于合成不同的 N-杂芳烃，包括不同的吡啶和喹啉。不同产物的选择性合成可以通过使用烯胺酮或烯胺酮/苯胺作为反应伙伴来实现。此外，与使用传统醛合成子的反应相比，雕白粉在更温和的条件下提供具有更高产率的产品方面显示出明显的优势。已经对反应过程进行了 GC-MS 分析，以探讨可能的反应机理。
• Recyclization of polysubstituted pyridinium salts
  作者：Galina P. Shkil、Viesturs Lusis、Dzintra Muceniece、Reva S. Sagitullin

  DOI：10.1016/0040-4020(95)00474-m

  日期：1995.7

  3,5-Diacetyl- and 3,5-dicyano-1,2,6-trimethylpyridinium perchlorates are converted by recyclization into N,5-dimethylanilines and 2-methylaminopyridines, respectively.