(3S,6S)-1,4-N,N-((S)-1-phenyleth-1-yl)-3,6-dimethylpiperazine-2,5-dione | 143746-60-5

• 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: (3S,6S)-1,4-N,N-((S)-1-phenyleth-1-yl)-3,6-dimethylpiperazine-2,5-dione
• 英文别名: (3S,6S)-3,6-dimethyl-1,4-bis[(1S)-1-phenylethyl]piperazine-2,5-dione
• CAS: 143746-60-5
• 化学式: C₂₂H₂₆N₂O₂
• 分子量: 350.461
• InChiKey: ANWSQVNRBMKJDE-XSLAGTTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  (3S,6S)-1,4-N,N-((S)-1-phenyleth-1-yl)-3,6-dimethylpiperazine-2,5-dione 在 氢碘酸 作用下， 反应 1.0h， 以90%的产率得到L-丙氨酸
  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：

  (S)-(-)- α-甲基苄胺 在 正丁基锂 、 sodium carbonate 、 potassium carbonate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 水 、 丙酮 为溶剂， 反应 25.0h， 生成 (3S,6S)-1,4-N,N-((S)-1-phenyleth-1-yl)-3,6-dimethylpiperazine-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

• (S)-α-methyl,α-amino acids: a new stereocontrolled synthesis
  作者：Daniele Balducci、Ilaria Lazzari、Magda Monari、Fabio Piccinelli、Gianni Porzi

  DOI：10.1007/s00726-009-0289-9

  日期：2010.3

  A new and convenient stereocontrolled synthesis of the optically pure (S)-α-methyl,α-amino acids 6(a–d) that exploits the chiral synthon 1,4-N,N-[(S)-1-phenylethyl]-piperazine-2,5-dione (1) is described. The (S)-1-phenylethyl group, bonded to each of the N-atoms of the 2,5-diketopiperazine, acts as a chiral inductor in the first alkylation, while the steric hindrance appears to be the determining factor

  利用手性合成子1,4- N，N -[（S）-1-苯乙基]的光学纯（S）-α-甲基，α-氨基酸6（a - d）的新型便捷立体合成方法描述了-哌嗪-2，5-二酮（1）。（S）-1-苯基乙基与2,5-二酮哌嗪的每个N-原子键合，在第一个烷基化反应中用作手性诱导剂，而空间位阻似乎是第三个烷基化立体控制的决定因素来回烷基化。
• 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.