(4S)-N-((S)-1-phenyleth-1-yl)-4-phenyl-3-((2R)-2-chloropropion-1-yl)-3-azapentanamide | 143746-59-2

• 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: (4S)-N-((S)-1-phenyleth-1-yl)-4-phenyl-3-((2R)-2-chloropropion-1-yl)-3-azapentanamide
• 英文别名: (2R)-2-chloro-N-[2-oxo-2-[[(1S)-1-phenylethyl]amino]ethyl]-N-[(1S)-1-phenylethyl]propanamide
• CAS: 143746-59-2
• 化学式: C₂₁H₂₅ClN₂O₂
• 分子量: 372.895
• InChiKey: PFFHYWMMHXQTIH-IKGGRYGDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4S)-N-((S)-1-phenyleth-1-yl)-4-phenyl-3-((2R)-2-chloropropion-1-yl)-3-azapentanamide 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 以92%的产率得到3(S)-3-methyl-1,4-di-<<(S)-1-phenylethyl>piperazine>-2,5-dione
  参考文献：
  名称：

  Diastereoselective alkylation of (3S)- and (3R)-3-methylpiperazine-2,5-dione derivatives. A convenient approach to both (S)- and (R)-alanine

  摘要：

  Treatment of (3S)-3-methylpiperazine-2,5-dione 6a with LHDMS followed by alkylation of the corresponding enolate with methyl iodide affords (3S,6S)-3,6-dimethyl derivative 7 in 98% de. The same reaction sequence carried out on (3R)-derivative 6b leads to a 93:7 diastereomeric mixture of (3R,6R)-8a and (3R,6S)-8b. Cleavage of the heterocyclic ring of 7 and ga with 57% HI leads to (S)- and (R)-alanine, respectively. The configuration at C-3 (of 6a and 6b) and at C-6 (of 7 and 8a) can be assigned on the basis of H-1 NMR spectroscopy and conformational analysis performed by MMPMI.

  DOI：

  10.1021/jo00050a030
• 作为产物：
  描述：

  2-chloro-N-((1S)-1-phenylethyl)acetamide 在 sodium carbonate 、 potassium carbonate 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 反应 19.0h， 生成 (4S)-N-((S)-1-phenyleth-1-yl)-4-phenyl-3-((2R)-2-chloropropion-1-yl)-3-azapentanamide
  参考文献：
  名称：

  Diastereoselective alkylation of (3S)- and (3R)-3-methylpiperazine-2,5-dione derivatives. A convenient approach to both (S)- and (R)-alanine

  摘要：

  Treatment of (3S)-3-methylpiperazine-2,5-dione 6a with LHDMS followed by alkylation of the corresponding enolate with methyl iodide affords (3S,6S)-3,6-dimethyl derivative 7 in 98% de. The same reaction sequence carried out on (3R)-derivative 6b leads to a 93:7 diastereomeric mixture of (3R,6R)-8a and (3R,6S)-8b. Cleavage of the heterocyclic ring of 7 and ga with 57% HI leads to (S)- and (R)-alanine, respectively. The configuration at C-3 (of 6a and 6b) and at C-6 (of 7 and 8a) can be assigned on the basis of H-1 NMR spectroscopy and conformational analysis performed by MMPMI.

  DOI：

  10.1021/jo00050a030

文献信息

• Diastereoselective alkylation of (3S)- and (3R)-3-methylpiperazine-2,5-dione derivatives. A convenient approach to both (S)- and (R)-alanine
  作者：Mario Orena、Gianni Porzi、Sergio Sandri

  DOI：10.1021/jo00050a030

  日期：1992.11

  Treatment of (3S)-3-methylpiperazine-2,5-dione 6a with LHDMS followed by alkylation of the corresponding enolate with methyl iodide affords (3S,6S)-3,6-dimethyl derivative 7 in 98% de. The same reaction sequence carried out on (3R)-derivative 6b leads to a 93:7 diastereomeric mixture of (3R,6R)-8a and (3R,6S)-8b. Cleavage of the heterocyclic ring of 7 and ga with 57% HI leads to (S)- and (R)-alanine, respectively. The configuration at C-3 (of 6a and 6b) and at C-6 (of 7 and 8a) can be assigned on the basis of H-1 NMR spectroscopy and conformational analysis performed by MMPMI.