syn,anti-N-isopropyl-N,2,4-trimethylnicotinamide | 129918-87-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: syn,anti-N-isopropyl-N,2,4-trimethylnicotinamide
• 英文别名: N,2,4-trimethyl-N-propan-2-ylpyridine-3-carboxamide
• CAS: 129918-87-2
• 化学式: C₁₂H₁₈N₂O
• 分子量: 206.288
• InChiKey: DANLAALXBYSQMR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  33.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-异丙基甲胺 、 2,4-dimethylnicotinoyl chloride hydrochloride 以 二氯甲烷 为溶剂， 反应 3.0h， 以71%的产率得到syn,anti-N-isopropyl-N,2,4-trimethylnicotinamide
  参考文献：
  名称：

  Conformational interlocking in axially chiral methyl N-(2',4'-dimethylnicotinoyl)-N-methylphenylalaninates

  摘要：

  Axially chiral 2,4-dimethylnicotinamides incorporating a protected N-methylphenylalanine moiety (1;2) have been prepared to serve as NAD+ model precursors. Starting from L- or D-methyl N-methylphenylalaninate hydrochloride ((S)- or (R)-4), the M-syn diastereomer 1a or its P-syn enantiomer 2a, were isolated in fair yield by a combination of rotamerization, helical isomerization, and crystallization. Evidence is presented for a strong conformational preference in solution not only at the amide bond but also at the chiral center (C-2) and at the benzylic carbon (C-3). The conformational interdependence compares well with the spatial arrangement in crystals of analogous axially chiral nicotinamide derivatives. Due to a preferred syn orientation of the amide carbonyl and C-2-H, the phenyl ring of the less polar syn diastereomers resides near the C-2' methyl group either at the alpha side of the pyridine ring in 1a or at the beta side in 2a. In these syn diastereomers in S chirality in the amino acid residue (i.e., in 1a) corresponds to a CO UP of M helicity, the R chirality (i.e., in 2a) to a CO DOWN or P orientation. Conversely, the phenyl ring of the more polar syn diastereomers 1b (P conformer) and 2b (M conformer) resides preferentially in the vicinity of the C-4' methyl group.

  DOI：

  10.1021/jo00001a005

文献信息

• VEKEMANS, JOZEF A. J. M.;BOOGERS, JEROEN A. F.;BUCK, HENK M., J. ORG. CHEM., 56,(1991) N, C. 10-16
  作者：VEKEMANS, JOZEF A. J. M.、BOOGERS, JEROEN A. F.、BUCK, HENK M.

  DOI：——

  日期：——
• Conformational interlocking in axially chiral methyl N-(2',4'-dimethylnicotinoyl)-N-methylphenylalaninates
  作者：Jozef A. J. M. Vekemans、Jeroen A. F. Boogers、Henk M. Buck

  DOI：10.1021/jo00001a005

  日期：1991.1

  Axially chiral 2,4-dimethylnicotinamides incorporating a protected N-methylphenylalanine moiety (1;2) have been prepared to serve as NAD+ model precursors. Starting from L- or D-methyl N-methylphenylalaninate hydrochloride ((S)- or (R)-4), the M-syn diastereomer 1a or its P-syn enantiomer 2a, were isolated in fair yield by a combination of rotamerization, helical isomerization, and crystallization. Evidence is presented for a strong conformational preference in solution not only at the amide bond but also at the chiral center (C-2) and at the benzylic carbon (C-3). The conformational interdependence compares well with the spatial arrangement in crystals of analogous axially chiral nicotinamide derivatives. Due to a preferred syn orientation of the amide carbonyl and C-2-H, the phenyl ring of the less polar syn diastereomers resides near the C-2' methyl group either at the alpha side of the pyridine ring in 1a or at the beta side in 2a. In these syn diastereomers in S chirality in the amino acid residue (i.e., in 1a) corresponds to a CO UP of M helicity, the R chirality (i.e., in 2a) to a CO DOWN or P orientation. Conversely, the phenyl ring of the more polar syn diastereomers 1b (P conformer) and 2b (M conformer) resides preferentially in the vicinity of the C-4' methyl group.