(2R)-2-Methoxy-N-((1'R)-phenylethyl)propanamide

• 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: (2R)-2-Methoxy-N-((1'R)-phenylethyl)propanamide
• 英文别名: (2R)-2-methoxy-N-[(1R)-1-phenylethyl]propanamide
• 化学式: C₁₂H₁₇NO₂
• 分子量: 207.272
• InChiKey: JABQQVRVONDPKW-NXEZZACHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  甲醇 、 (2S)-2-Bromo-N-((1'R)-phenylethyl)propanamide 在 银 作用下， 反应 28.0h， 生成 (2R)-2-Methoxy-N-((1'R)-phenylethyl)propanamide
  参考文献：
  名称：

  Stereoselective Substitution in 2-Bromo Amides in the Presence of Ag+ or Ag2O

  摘要：

  Bromine displacement by a primary, secondary, or tertiary amine, or methanol, in chiral nonracemic (S)-2-bromopropanamides 1 occurs with high yields and stereo selectivity. Soluble Ag+ promotes inversion, and solid Ag2O promotes retention of configuration. However, in the case of Et(3)N, Ag+ promotes retention. With the hindered 2-bromo-2-methylbutanamide 5, the displacement by a primary or secondary amine or methanol occurs only in the presence of Ag2O, possibly with retention of configuration.

  DOI：

  10.1021/jo00118a017

文献信息

• Mutual kinetic resolution of 3-methyl-3,4-dihydro-2H-1,4-benzoxazines and 2-alkoxyacyl chlorides
  作者：Sergey A. Vakarov、Dmitry А. Gruzdev、Liliya Sh. Sadretdinova、Mikhail I. Kodess、Andrey A. Tumashov、Evgeny B. Gorbunov、Galina L. Levit、Victor P. Krasnov

  DOI：10.1007/s10593-018-2286-y

  日期：2018.4

  Stereoselective acylation of racemic 3-methyl-3,4-dihydro-2Н-1,4-benzoxazine and its 7,8-difluoro-substituted analog with racemic 2-alkoxyacyl chlorides was stidied. The reactions of 3-methyl-3,4-dihydro-2H-1,4-benzoxazines with 2-methoxyisopentanoyl chloride were found to be more selective (selectivity factor s 31–32) compared to the acylation with other studied propanoyl chlorides (s 18–21). This

  的立体选择性酰化外消旋3-甲基-3,4-二氢-2- Н -1,4-苯并恶嗪及其与外消旋2-烷氧基酰基氯化物-7,8-二氟取代的类似物，stidied。发现3-甲基-3,4-二氢-2 H -1,4-苯并恶嗪与2-甲氧基异戊酰氯的反应比与其他已研究丙酰氯的酰化反应具有更高的选择性（选择性系数s 31–32）（š 18-21）。该事实可能是由于与衍生自丙酸的试剂中的甲基相比，酰氯中的异丙基取代基引起了明显的位阻。
• Stereoselective Substitution in 2-Bromo Amides in the Presence of Ag+ or Ag2O
  作者：Ferruccio D'Angeli、Paolo Marchetti、Valerio Bertolasi

  DOI：10.1021/jo00118a017

  日期：1995.6

  Bromine displacement by a primary, secondary, or tertiary amine, or methanol, in chiral nonracemic (S)-2-bromopropanamides 1 occurs with high yields and stereo selectivity. Soluble Ag+ promotes inversion, and solid Ag2O promotes retention of configuration. However, in the case of Et(3)N, Ag+ promotes retention. With the hindered 2-bromo-2-methylbutanamide 5, the displacement by a primary or secondary amine or methanol occurs only in the presence of Ag2O, possibly with retention of configuration.