(3R)-<3-methyl-1,4-bis(S)-1-phenylethyl>-piperazine-2,5-dione | 143837-99-4

• 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: (3R)-<3-methyl-1,4-bis(S)-1-phenylethyl>-piperazine-2,5-dione
• 英文别名: (3R)-3-methyl-1,4-di-<(S)-1-phenylethyl>piperazine-2,5-dione；(3R)-1,4-N,N-((S)-1-phenyleth-1-yl)-3-methylpiperazine-2,5-dione；(3R)-3-methyl-1,4-bis[(1S)-1-phenylethyl]piperazine-2,5-dione
• CAS: 143837-99-4
• 化学式: C₂₁H₂₄N₂O₂
• 分子量: 336.434
• InChiKey: XJUSIFMMTZBKOV-YESZJQIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3R)-<3-methyl-1,4-bis(S)-1-phenylethyl>-piperazine-2,5-dione 在 sodium tetrahydroborate 、 lithium hexamethyldisilazane 作用下， 以 异丙醇 为溶剂， 反应 31.0h， 生成 (3R,6R)-<6-<(R)-1-hydroxyethyl>-3-methyl-1,4-bis(S)-1-phenylethyl>piperazine-2,5-dione
  参考文献：
  名称：

  D'Arriego, M. Cristina; Porzi, Gianni; Rossetti, Monica, Journal of Chemical Research, Miniprint, 1995, # 5, p. 1038 - 1050

  摘要：

  DOI：
• 作为产物：
  描述：

  (4S)-N-((S)-1-phenyleth-1-yl)-4-phenyl-3-azapentanamide 在 正丁基锂 、 sodium carbonate 作用下， 以 四氢呋喃 、 正己烷 、 水 、 丙酮 为溶剂， 反应 13.0h， 生成 (3R)-<3-methyl-1,4-bis(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

文献信息

• Orena, Mario; Porzi, Gianni; Sandri, Sergio, Journal of Chemical Research, Miniprint, 1993, # 8, p. 2125 - 2152
  作者：Orena, Mario、Porzi, Gianni、Sandri, Sergio

  DOI：——

  日期：——
• 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.
• D'Arriego, M. Cristina; Porzi, Gianni; Rossetti, Monica, Journal of Chemical Research, Miniprint, 1995, # 5, p. 1038 - 1050
  作者：D'Arriego, M. Cristina、Porzi, Gianni、Rossetti, Monica、Sandri, Sergio

  DOI：——

  日期：——