methyl 1-benzyl-6-oxo-1,6-dihydropyridine-3-carboxylate | 77837-11-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: methyl 1-benzyl-6-oxo-1,6-dihydropyridine-3-carboxylate
• 英文别名: methyl N-benzylpyridone-5-carboxylate；methyl 1-benzyl-6-keto-1,6-dihydronicotinate；Methyl 1-benzyl-1,6-dihydro-6-oxopyridine-3-carboxylate；methyl 1-benzyl-6-oxopyridine-3-carboxylate
• CAS: 77837-11-7
• 化学式: C₁₄H₁₃NO₃
• mdl: MFCD00139921
• 分子量: 243.262
• InChiKey: XMGPGDWNOKZWRN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 1-benzyl-6-oxo-1,6-dihydropyridine-3-carboxylate 在 5%-palladium/activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 40.0 ℃ 、100.0 kPa 条件下， 反应 24.0h， 以29%的产率得到1-苄基-6-氧代哌啶-3-甲酸甲酯
  参考文献：
  名称：

  Synthesis and reduction reactions of pyridones and 5-acyl-2-methoxypyridines

  摘要：

  The synthesis of a series of pyridones, from their 2-hydroxypyridine or 2-methoxypyridine precursors, is described, along with studies into their reductions to saturated heterocycles. A number of 5-acylpyridones were prepared and were evaluated as substrates for asymmetric transfer hydrogenation prior to conversion to saturated heterocycles. The enantioselective reduction of 5-acetyl-1-benzylpyrimidine-2,4(1H,3H)-dione is also described. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.06.046
• 作为产物：
  描述：

  6-甲氧基烟酸 在 硫酸 、 potassium carbonate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 64.0h， 生成 methyl 1-benzyl-6-oxo-1,6-dihydropyridine-3-carboxylate
  参考文献：
  名称：

  Synthesis and reduction reactions of pyridones and 5-acyl-2-methoxypyridines

  摘要：

  The synthesis of a series of pyridones, from their 2-hydroxypyridine or 2-methoxypyridine precursors, is described, along with studies into their reductions to saturated heterocycles. A number of 5-acylpyridones were prepared and were evaluated as substrates for asymmetric transfer hydrogenation prior to conversion to saturated heterocycles. The enantioselective reduction of 5-acetyl-1-benzylpyrimidine-2,4(1H,3H)-dione is also described. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.06.046

文献信息

• 一种C3-烯基化的2-吡啶酮类衍生物的制备方法
  申请人：五邑大学

  公开号：CN113024604B

  公开（公告）日：2022-05-03

  本发明公开了一种C3‑烯基化的2‑吡啶酮类衍生物的制备方法，该制备方法包括以下步骤：将原料在催化体系下反应制得C3‑烯基化的2‑吡啶酮类衍生物。本发明的制备方法是原子经济性的，符合绿色化学的要求，在大规模生产过程中也不会产生其它副产物，达到了简化工艺、降低成本和减少环境污染的目的。
• Method for generating mature β-like cells
  申请人：The University of Western Australia

  公开号：US10568913B2

  公开（公告）日：2020-02-25

  The present invention relates to methods for generating mature insulin-producing β-like cells comprising the steps: (a) isolating, purifying and/or enriching β-cell progenitor cells from a population of cells; (b) differentiation of the β-cell progenitor cells into immature insulin-producing β-like cells; and (c) maturation of the immature insulin-producing β-like cells into mature insulin-producing β-like cells, comprising exposing the immature insulin-producing β-like cells to calcitriol or an analogue thereof. More particularly, the present invention relates to methods for generating mature insulin-producing β-like cells for use in treating diabetes.

  本发明涉及产生成熟的胰岛素分泌β样细胞的方法，包括以下步骤： (a)从细胞群中分离、纯化和/或富集β细胞祖细胞；(b)将β细胞祖细胞分化为未成熟的胰岛素分泌β样细胞；(c)将未成熟的胰岛素分泌β样细胞成熟为成熟的胰岛素分泌β样细胞，包括将未成熟的胰岛素分泌β样细胞暴露于钙三醇或其类似物。 更具体地说，本发明涉及产生用于治疗糖尿病的成熟胰岛素分泌β样细胞的方法。
• Copper-Catalyzed Regioselective Imidation of 2-Pyridones
  作者：Tamilarasu Murugesan、Shanawas Hussain Moulana Mahal、Kalyanakrishnan Arayil Vennoli、Dharsan Karthikeyan、Alagiri Kaliyamoorthy

  DOI：10.1021/acs.orglett.4c00681

  日期：2024.4.19

  We demonstrate a ligand- and glovebox-free regioselective direct C(3)–H imidation of 2-pyridones and also benzylic-type imidation of 2-pyridones bearing a methyl substituent employing Cu(OAc)2·H2O as the catalyst and N-fluorobenzenesulfonimide (NFSI) as an imidating reagent. A broad range of imidated 2-pyridone derivatives is made up to excellent yields. The present strategy operates well on a gram

  我们展示了2-吡啶酮的无配体和手套箱的区域选择性直接C(3)–H酰亚胺化以及使用Cu(OAc) 2 ·H 2 O作为催化剂对带有甲基取代基的2-吡啶酮的苄型酰亚胺化，并且N-氟苯磺酰亚胺 (NFSI) 作为酰亚胺化试剂。多种酰亚胺化 2-吡啶酮衍生物均具有优异的产率。本策略在克规模上运行良好，并且所得产物可以容易地进行单和双脱磺酰化反应。
• An annulation method for the synthesis of alkyl-substituted 6-carbomethoxy-2-pyridones
  作者：Yu Zhang、Brad M. Loertscher、Steven L. Castle

  DOI：10.1016/j.tet.2009.06.006

  日期：2009.8

  A protocol for the synthesis of 5-alkyl and 3,5-dialkyl-6-carbomethoxy-2-pyridones was devised. Key steps include a Mannich reaction, acylation of a tosylamine, and a PPh3/TiCl4-promoted intramolecular Reformatsky-type reaction with a thioester as the electrophile. The latter process typically afforded a vinylogous thiocarbamate via elimination of water rather than the Dieckmann-type product which would have resulted from elimination of the thiol. However, the Dieckmann-type ketone product was obtained in one instance. Subsequent elimination of the tosyl group and desulfurization completed the pyridone synthesis. (C) 2009 Elsevier Ltd. All rights reserved.
• Ligand-Controlled Ni(0)–Al(III) Bimetal-Catalyzed C3–H Alkenylation of 2-Pyridones by Reversing Conventional Selectivity
  作者：Ge Yin、Yue Li、Rong-Hua Wang、Jiang-Fei Li、Xue-Tao Xu、Yu-Xin Luan、Mengchun Ye

  DOI：10.1021/acscatal.1c00750

  日期：2021.4.16