(S)-N-methyl-N-(1-methyl-2-oxo-2-phenyl)benzamide | 171337-08-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-N-methyl-N-(1-methyl-2-oxo-2-phenyl)benzamide
• 英文别名: N-methyl-N-[(2S)-1-oxo-1-phenylpropan-2-yl]benzamide
• CAS: 171337-08-9
• 化学式: C₁₇H₁₇NO₂
• 分子量: 267.327
• InChiKey: ONMRTRSFSIYGHU-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-N-methyl-N-(1-methyl-2-oxo-2-phenyl)benzamide 在 甲基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 11.0h， 生成 (S)-N-methyl-3-phenyl-3-buten-2-amine
  参考文献：
  名称：

  Diastereoselective preparation of chiral lithiated allyl amines: Application in EPC-synthesis

  摘要：

  Lithiation of chiral allylamine (R)-1 with Bu(n)Li and Bu(t)Li leads to the formation of intermediate (R)-2, which by reaction with D2O, Me(2)CO or (CH2)(5)CO affords the expected chiral compounds (R)-3, (R)-4 and (R)-5, respectively. With Bu(1)CHO the corresponding aminoalcohols (R,R)6 and(R,S)-6 are separated in pure form by their transformation into the corresponding benzamides 6', which yield again the precursor aminoalcohols with MeLi. The carbonation of (R)-2 followed by esterification affords the unexpected ester trans- (R)-7. The same set of reactions is carried out with (S)-1 yielding the corresponding series of(S) derivatives. X-Ray analysis of(S,S)-6' allows the assignement of the stereochemistry for all aminoalcohols 6. The same processes are applied to more substituted chiralamines (R)- and (S)-11 obtaining the corresponding chiral products (R)- and (S)-13 and (S)-14.

  DOI：

  10.1016/0957-4166(95)00271-p
• 作为产物：
  描述：

  (-)-N-benzoyl-ephedrine 在 Celite 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 (S)-N-methyl-N-(1-methyl-2-oxo-2-phenyl)benzamide
  参考文献：
  名称：

  Diastereoselective preparation of chiral lithiated allyl amines: Application in EPC-synthesis

  摘要：

  Lithiation of chiral allylamine (R)-1 with Bu(n)Li and Bu(t)Li leads to the formation of intermediate (R)-2, which by reaction with D2O, Me(2)CO or (CH2)(5)CO affords the expected chiral compounds (R)-3, (R)-4 and (R)-5, respectively. With Bu(1)CHO the corresponding aminoalcohols (R,R)6 and(R,S)-6 are separated in pure form by their transformation into the corresponding benzamides 6', which yield again the precursor aminoalcohols with MeLi. The carbonation of (R)-2 followed by esterification affords the unexpected ester trans- (R)-7. The same set of reactions is carried out with (S)-1 yielding the corresponding series of(S) derivatives. X-Ray analysis of(S,S)-6' allows the assignement of the stereochemistry for all aminoalcohols 6. The same processes are applied to more substituted chiralamines (R)- and (S)-11 obtaining the corresponding chiral products (R)- and (S)-13 and (S)-14.

  DOI：

  10.1016/0957-4166(95)00271-p

文献信息

• Diastereoselective preparation of chiral lithiated allyl amines: Application in EPC-synthesis
  作者：Miguel Yus、Francisco Foubelo、Larry R. Falvello

  DOI：10.1016/0957-4166(95)00271-p

  日期：1995.8

  Lithiation of chiral allylamine (R)-1 with Bu(n)Li and Bu(t)Li leads to the formation of intermediate (R)-2, which by reaction with D2O, Me(2)CO or (CH2)(5)CO affords the expected chiral compounds (R)-3, (R)-4 and (R)-5, respectively. With Bu(1)CHO the corresponding aminoalcohols (R,R)6 and(R,S)-6 are separated in pure form by their transformation into the corresponding benzamides 6', which yield again the precursor aminoalcohols with MeLi. The carbonation of (R)-2 followed by esterification affords the unexpected ester trans- (R)-7. The same set of reactions is carried out with (S)-1 yielding the corresponding series of(S) derivatives. X-Ray analysis of(S,S)-6' allows the assignement of the stereochemistry for all aminoalcohols 6. The same processes are applied to more substituted chiralamines (R)- and (S)-11 obtaining the corresponding chiral products (R)- and (S)-13 and (S)-14.