2-(dimethylamino)-3-methyleneisoindolin-1-one | 55740-93-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-(dimethylamino)-3-methyleneisoindolin-1-one
• 英文别名: 2-(Dimethylamino)-3-methylideneisoindol-1-one
• CAS: 55740-93-7
• 化学式: C₁₁H₁₂N₂O
• 分子量: 188.229
• InChiKey: DUTZBQABSNUCRB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  联硼酸频那醇酯 、 2-(dimethylamino)-3-methyleneisoindolin-1-one 在 chloro[1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene]copper(I) 、 caesium carbonate 作用下， 以 甲醇 为溶剂， 以40 %的产率得到2-(dimethylamino)-3-((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)isoindolin-1-one
  参考文献：
  名称：

  Copper-Catalyzed Hydroboration of Enamides with Bis(pinacolato)diboron: Promising Agents with Antimicrobial Activities

  摘要：

  We reported in this study the hydroboration of enamides in methanol at room temperature catalyzed by copper complexes. Under such conditions, a Gram-scale reaction with a high yield was also completed. Hydroboration of 3-methylene, 2-(alkyl and phenylisoindolin-1-one 5 with bis(pinacolato)diboron yields the respective compounds 6 in good yields with high-to-moderate enantioselectivity (58% ee). Furthermore, the antimicrobial properties of the synthesized compounds were tested against four indicator microorganisms: the two Gram-positive bacteria L. monocytogenes ATCC 1911 and S. aureus ATCC 6538, the Gram-negative bacterium S. typhimurium ATCC 14028, and the fungus C. albicans (ATCC 90028). The MIC values of compounds 5-6 range from 0.312 to 2.5 (μg/mL) against L. monocytogenes, from 2.1 to 0.136 (μg/mL) against S. aureus, and from 0.126 to 0.923 (μg/mL) against S. typhimurium.

  DOI：

  10.1155/2022/6577185
• 作为产物：
  描述：

  N',N'-dimethyl-2-bromobenzohydrazide 在 正丁基锂 、 双(三甲基硅烷基)氨基钾 、 对甲苯磺酸 、 苯基锂 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 0.25h， 生成 2-(dimethylamino)-3-methyleneisoindolin-1-one
  参考文献：
  名称：

  一种新的通用合成路线，可合成2-二甲基氨基-3-烷基和芳基亚甲基-2,3-二氢-1 H-异吲哚-1-酮

  摘要：

  已经通过合适的3-苯并三唑基取代的母体模型通过涉及去质子化的三步顺序有效地制备了各种2-二甲基氨基-3-烷基和芳基亚甲基-2,3-二氢-1H-异吲哚-1-酮，随后酸处理引起的烷基化和最终消除反应。

  DOI：

  10.1016/s0040-4039(02)01972-x

文献信息

• Base‐ and Visible‐Light‐Promoted Formation of 3‐Benzyl‐3‐Methoxyisoindolin‐1‐one
  作者：Nathan Martin、Aurélien Moncomble、Lydie Pélinski、Eric Deniau、Till Bousquet

  DOI：10.1002/ejoc.202400025

  日期：2024.5.13

  Aryl diazonium salts are versatile compounds known for their reactivity in various transformations. In this study, we explored the arylation of 3‐methylene isoindolinones using aryl diazonium salts. The objective was to develop a method for accessing 3‐benzyl‐3‐methoxyisoindolin‐1‐ones, a class of compounds with diverse biological activities and synthetic importance. Optimization of the reaction conditions revealed the significance of light irradiation for improved yields. The substrate scope investigation demonstrated the compatibility of various diazonium salts and N‐substituents on the 3‐methylene isoindolinone scaffold, yielding the corresponding methoxy lactams with high yields. Mechanistic insights were obtained by observing the effect of base and light irradiation. Two initiation mechanisms were proposed: in the presence of a base, the reaction could proceed even without light irradiation, while light irradiation was necessary in the absence of a base. DFT calculations were performed to elucidate the mechanism of the reaction and provide energetic considerations