1-(2,4-二甲氧基苄基)-1,5-二氢-2H-吡咯-2-酮 | 1009808-80-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(2,4-二甲氧基苄基)-1,5-二氢-2H-吡咯-2-酮
• 英文名称: 1-(2,4-dimethoxybenzyl)-1,5-dihydro-2H-pyrrol-2-one
• 英文别名: 1-[(2,4-dimethoxyphenyl)methyl]-2H-pyrrol-5-one
• CAS: 1009808-80-3
• 化学式: C₁₃H₁₅NO₃
• 分子量: 233.267
• InChiKey: YCISODDOBUGZCK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-(2,4-dimethoxybenzyl)-N-prop-2-en-1-ylprop-2-enamide 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以95%的产率得到1-(2,4-二甲氧基苄基)-1,5-二氢-2H-吡咯-2-酮
  参考文献：
  名称：

  Tandem RCM−Isomerization− Cyclopropanation Reactions

  摘要：

  A new triple tandem process has been discovered in which simple acyclic substrates can be transformed into bicyclic compounds via RCM-double bond isomerization-cyclopropanation. This process is catalyzed by second generation Grubb's catalyst without the requirement of other reactives or additives. In addition, a one-pot RCM-isomerization reaction followed by cyclopropanation with CHCl3/NaOH allows the synthesis of products related to NOS (nitric oxide synthase) inhibitors, which are currently under clinical evaluation.

  DOI：

  10.1021/ol702766h

文献信息

• Lactam Strategy Using Amide-Selective Nucleophilic Addition for Quick Access to Complex Amines: Unified Total Synthesis of Stemoamide-Type Alkaloids
  作者：Yasukazu Sugiyama、Yasuki Soda、Makoto Yoritate、Hayato Tajima、Yoshito Takahashi、Kana Shibuya、Chisato Ogihara、Takashi Yokoyama、Takeshi Oishi、Takaaki Sato、Noritaka Chida

  DOI：10.1246/bcsj.20210372

  日期：2022.2.15

  chemoselective nucleophilic addition of unsaturated lactone derivatives provides tetracyclic natural products. While stemonine is obtained by an Ir-catalyzed lactam-selective reductive Mannich reaction, saxorumamide and isosaxorumamide are produced through the lactone-selective nucleophilic addition of the lithiated 2-silyl-furan. The developed conditions for the lactam-selective nucleophilic reactions

  我们的研究小组一直在探索一种用于复杂生物碱的简明全合成的内酰胺策略。在本文中，我们报告了基于内酰胺策略的五元环化学选择性组装统一全合成茎酰胺类生物碱的全部细节。首先，通过不饱和γ-内酰胺与不饱和γ-内酯的插藤迈克尔加成-还原序列，实现了三环茎酰胺的简明和克级合成，然后是N-烷基化形成七元环。干酪酰胺作为一种常见的中间体，不饱和内酯衍生物的化学选择性亲核加成提供了四环天然产物。干草碱是通过 Ir 催化的内酰胺选择性还原曼尼希反应获得的，而 saxorumamide 和 isosaxorumamide 则是通过锂化的 2-甲硅烷基呋喃的内酯选择性亲核加成产生的。所开发的内酰胺选择性亲核反应条件非常通用，并且被发现适用于五环茎莨菪碱和异骨莴苣素的全合成。该策略使三环、四环和五环干酰胺类生物碱的简明和统一的全合成能够在 12 个步骤内从市售化合物中获得。
• Tandem RCM−Isomerization− Cyclopropanation Reactions
  作者：Álvaro Mallagaray、Gema Domínguez、Ana Gradillas、Javier Pérez-Castells

  DOI：10.1021/ol702766h

  日期：2008.2.1

  A new triple tandem process has been discovered in which simple acyclic substrates can be transformed into bicyclic compounds via RCM-double bond isomerization-cyclopropanation. This process is catalyzed by second generation Grubb's catalyst without the requirement of other reactives or additives. In addition, a one-pot RCM-isomerization reaction followed by cyclopropanation with CHCl3/NaOH allows the synthesis of products related to NOS (nitric oxide synthase) inhibitors, which are currently under clinical evaluation.