2-(2,4-dimethoxybenzylamino)-N-methylethanamide | 1095558-23-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(2,4-dimethoxybenzylamino)-N-methylethanamide
• 英文别名: 2-[(2,4-dimethoxyphenyl)methylamino]-N-methylacetamide
• CAS: 1095558-23-8
• 化学式: C₁₂H₁₈N₂O₃
• mdl: MFCD11637330
• 分子量: 238.287
• InChiKey: BTYPGGOXCHGZJT-UHFFFAOYSA-N

物化性质

• 沸点：
  421.2±40.0 °C(Predicted)
• 密度：
  1.092±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  59.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2,4-dimethoxybenzylamino)-N-methylethanamide 、 草酰基二咪唑 以 乙二醇二甲醚 为溶剂， 反应 12.0h， 以65%的产率得到1-(2,4-dimethoxybenzyl)-4-methylpiperazine-2,3,5-trione
  参考文献：
  名称：

  Enantioselective Total Synthesis of (+)-Gliocladine C: Convergent Construction of Cyclotryptamine-Fused Polyoxopiperazines and a General Approach for Preparing Epidithiodioxopiperazines from Trioxopiperazine Precursors

  摘要：

  A concise second-generation total synthesis of the fungal-derived alkaloid (+)-gliocladin C (11) in 10 steps and 1196 overall yield from isatin is reported. In addition, the epipolythiodioxopiperazine (ETP) natural product (+)-gliocladine C (6) has been prepared in six steps and 2996 yield from the di-(tert-butoxycarbonyl) precursor of 11. The total synthesis of 6 constitutes the first total synthesis of an ETP natural product containing a hydroxyl substituent adjacent to a quaternary carbon stereocenter in the pyrrolidine ring.

  DOI：

  10.1021/ja201789v
• 作为产物：
  描述：

  H-甘氨酸-NHME盐酸盐 、 2,4-二甲氧基苯甲醛 在 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 3.25h， 以70%的产率得到2-(2,4-dimethoxybenzylamino)-N-methylethanamide
  参考文献：
  名称：

  Enantioselective Total Synthesis of (+)-Gliocladine C: Convergent Construction of Cyclotryptamine-Fused Polyoxopiperazines and a General Approach for Preparing Epidithiodioxopiperazines from Trioxopiperazine Precursors

  摘要：

  A concise second-generation total synthesis of the fungal-derived alkaloid (+)-gliocladin C (11) in 10 steps and 1196 overall yield from isatin is reported. In addition, the epipolythiodioxopiperazine (ETP) natural product (+)-gliocladine C (6) has been prepared in six steps and 2996 yield from the di-(tert-butoxycarbonyl) precursor of 11. The total synthesis of 6 constitutes the first total synthesis of an ETP natural product containing a hydroxyl substituent adjacent to a quaternary carbon stereocenter in the pyrrolidine ring.

  DOI：

  10.1021/ja201789v

文献信息

• Enantioselective Total Synthesis of (+)-Gliocladine C: Convergent Construction of Cyclotryptamine-Fused Polyoxopiperazines and a General Approach for Preparing Epidithiodioxopiperazines from Trioxopiperazine Precursors
  作者：John E. DeLorbe、Salman Y. Jabri、Steven M. Mennen、Larry E. Overman、Fang-Li Zhang

  DOI：10.1021/ja201789v

  日期：2011.5.4

  A concise second-generation total synthesis of the fungal-derived alkaloid (+)-gliocladin C (11) in 10 steps and 1196 overall yield from isatin is reported. In addition, the epipolythiodioxopiperazine (ETP) natural product (+)-gliocladine C (6) has been prepared in six steps and 2996 yield from the di-(tert-butoxycarbonyl) precursor of 11. The total synthesis of 6 constitutes the first total synthesis of an ETP natural product containing a hydroxyl substituent adjacent to a quaternary carbon stereocenter in the pyrrolidine ring.