N-benzyl-3,4-dimethyl-5-methoxy-3-pyrrolin-2-one | 244124-73-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-benzyl-3,4-dimethyl-5-methoxy-3-pyrrolin-2-one
• 英文别名: 1-benzyl-5-methoxy-3,4-dimethyl-1,5-dihydro-2H-pyrrol-2-one；1-benzyl-2-methoxy-3,4-dimethyl-2H-pyrrol-5-one
• CAS: 244124-73-0
• 化学式: C₁₄H₁₇NO₂
• 分子量: 231.294
• InChiKey: BDTMQUOWMAHRJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-benzyl-3,4-dimethyl-5-methoxy-3-pyrrolin-2-one 在 五氯化磷 作用下， 以 正己烷 、 乙腈 为溶剂， 反应 3.0h， 生成 1-benzyl-5-[(2-chloroethyl)amino]-3,4-dimethyl-1,5-dihydro-2H-pyrrol-2-one
  参考文献：
  名称：

  5-氯取代 1,5-Dihydro-2H-pyrrol-2-ones 作为中间体用于高效合成 5-烷基氨基、5-叠氮基、5-烷氧基氨基和 5-烷氧基衍生物

  摘要：

  5-羟基-1,5-二氢-2H-吡咯-2-酮被转化为 5-氯-1,5-二氢-2H-吡咯-2-酮 1a-d。这些化合物被证明是制备各种 5-烷氧基、5-烷基氨基、5-烷氧基氨基和 5-叠氮衍生物的有用中间体，产量很高。

  DOI：

  10.1055/s-2001-9757
• 作为产物：
  描述：

  lithium methanolate 、 1-Benzyl-3-chloro-4-(chloromethyl)-3-methylpyrrolidin-2-one 以 甲醇 、 乙醚 为溶剂， 反应 24.0h， 以78%的产率得到N-benzyl-3,4-dimethyl-5-methoxy-3-pyrrolin-2-one
  参考文献：
  名称：

  Unusual access to 5-methoxy or 5,5-dimethoxy-4-methyl-3-pyrrolin-2-ones from chlorinated 4-methyl-pyrrolidin-2-ones

  摘要：

  The reaction of N-substituted 4-methyl-2-pyrrolidinones, carrying not less than two chlorine atoms on the C(3) and C(6) carbons afforded with alkaline methoxide in methanol, under mild conditions, the corresponding 5-methoxy or 5,5-dimethoxy-4-methyl-3-pyrrolin-2-ones in satisfactory yields. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00792-4

文献信息

• Synthesis of 5-alkyl- and 5-aryl-1,5-dihydro-2<i>H</i>-pyrrol-2-ones via coupling of <i>5</i>-chloro-1,5-dihydro-2<i>H</i>-pyrrol-2-ones with organometallic compounds
  作者：Kirill V Nikitin、Nonna P Andryukhova

  DOI：10.1139/v00-127

  日期：2000.10.1

  5-Chloro-1,5-dihydro-2H-pyrrol-2-ones are easily alkylated at the 5-position by organomagnesium or organozinc compounds and diethyl sodiomalonate leading to corresponding 5-alkyl-1,5-dihydro-2H-pyrrol-2-ones in high yields.Key words: organometallic compounds, alkylation, 1,5-dihydro-2H-pyrrol-2-one.

  5-氯-1,5-二氢-2H-吡咯-2-酮在5位易受有机镁或有机锌化合物和乙酰丙二酸二乙酯钠的烷基化作用，从而产生对应的5-烷基-1,5-二氢-2H-吡咯-2-酮，收率高。关键词：有机金属化合物，烷基化，1,5-二氢-2H-吡咯-2-酮。
• Synthesis of 5-methoxylated 3-pyrrolin-2-ones via the rearrangement of chlorinated pyrrolidin-2-ones
  作者：Franco Ghelfi、Christian V Stevens、Inge Laureyn、Ellen Van Meenen、Tina M Rogge、Laurent De Buyck、Kirill V Nikitin、Romano Grandi、Emanuela Libertini、Ugo M Pagnoni、Luisa Schenetti

  DOI：10.1016/s0040-4020(03)00044-9

  日期：2003.2

  The reaction of N-substituted 4-methyl-2-pyrrolidinones or 4-diethoxyphosphoryl analogues, carrying at least two chlorine atoms between the C(3) and C(6) carbons, with alkaline methoxide in methanol afforded the corresponding 5-methoxylated 3-pyrrolin-2-ones, useful adducts for the preparation of agrochemicals or medicinal compounds. (C) 2003 Elsevier Science Ltd. All rights reserved.
• 5-Chloro Substituted 1,5-Dihydro-2H-pyrrol-2-ones as Intermediates for the Efficient Synthesis of 5-Alkylamino, 5-Azido, 5-Alkoxyamino, and 5-Alkoxy Derivatives
  作者：Kirill V. Nikitin、Nonna P. Andryukhova

  DOI：10.1055/s-2001-9757

  日期：——

  5-Hydroxy-1,5-dihydro-2H-pyrrol-2-ones were converted to 5-chloro-1,5-dihydro-2H-pyrrol-2-ones 1a-d. These compounds are shown to be useful intermediates for the preparation of various 5-alkoxy, 5-alkylamino, 5-alkoxyamino, and 5-azido derivatives in high yields.

  5-羟基-1,5-二氢-2H-吡咯-2-酮被转化为 5-氯-1,5-二氢-2H-吡咯-2-酮 1a-d。这些化合物被证明是制备各种 5-烷氧基、5-烷基氨基、5-烷氧基氨基和 5-叠氮衍生物的有用中间体，产量很高。
• Unusual access to 5-methoxy or 5,5-dimethoxy-4-methyl-3-pyrrolin-2-ones from chlorinated 4-methyl-pyrrolidin-2-ones
  作者：Franco Bellesia、Laurent De Buyck、Maria V. Colucci、Franco Ghelfi、Inge Laureyn、Emanuela Libertini、Adele Mucci、Ugo M. Pagnoni、Adriano Pinetti、Tina M. Rogge、Christian V. Stevens

  DOI：10.1016/s0040-4039(01)00792-4

  日期：2001.7

  The reaction of N-substituted 4-methyl-2-pyrrolidinones, carrying not less than two chlorine atoms on the C(3) and C(6) carbons afforded with alkaline methoxide in methanol, under mild conditions, the corresponding 5-methoxy or 5,5-dimethoxy-4-methyl-3-pyrrolin-2-ones in satisfactory yields. (C) 2001 Elsevier Science Ltd. All rights reserved.