2,5-Piperazinedione, 3-methyl-6-(1-methylethyl)-, (3R,6S)-

• 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: 2,5-Piperazinedione, 3-methyl-6-(1-methylethyl)-, (3R,6S)-
• 英文别名: (3R,6S)-3-methyl-6-propan-2-ylpiperazine-2,5-dione
• 化学式: C₈H₁₄N₂O₂
• 分子量: 170.211
• InChiKey: ORLDMMKUTCCBSM-RITPCOANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,5-Piperazinedione, 3-methyl-6-(1-methylethyl)-, (3R,6S)- 在 盐酸 、 水 作用下， 反应 24.0h， 生成 D-丙氨酸 、 L-缬氨酸
  参考文献：
  名称：

  A chiral relay auxiliary for the synthesis of homochiral α-amino acids

  摘要：

  我们开发了一种新的手性辅助剂 (3S)-N,Nâ²-双（对甲氧基苄基）-3-异丙基哌嗪-2,5-二酮 7，用于δ-氨基酸的不对称合成。辅助剂 7 采用了一种基于非固有 N-苄基保护基团的新型手性中继网络，从而提高了其 C6 对映体 25 烷基化过程中观察到的非对映选择性。

  DOI：

  10.1039/a803124j
• 作为产物：
  描述：

  (3S,6R)-N,N'-bis-(p-methoxybenzyl)-3-isopropyl-6-methyl-piperazine-2,5-dione 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 4.0h， 以94%的产率得到2,5-Piperazinedione, 3-methyl-6-(1-methylethyl)-, (3R,6S)-
  参考文献：
  名称：

  A chiral relay auxiliary for the synthesis of homochiral α-amino acids

  摘要：

  我们开发了一种新的手性辅助剂 (3S)-N,Nâ²-双（对甲氧基苄基）-3-异丙基哌嗪-2,5-二酮 7，用于δ-氨基酸的不对称合成。辅助剂 7 采用了一种基于非固有 N-苄基保护基团的新型手性中继网络，从而提高了其 C6 对映体 25 烷基化过程中观察到的非对映选择性。

  DOI：

  10.1039/a803124j

文献信息

• Acetic acid-catalyzed diketopiperazine synthesis.
  作者：KENJI SUZUKI、YUSUKE SASAKI、NOBUYOSHI ENDO、YUICHI MIHARA

  DOI：10.1248/cpb.29.233

  日期：——

  Optically pure diketopiperazines were obtained in good yields when dipeptide esters were refluxed in 2-butanol containing 0.1 M acetic acid for 3 hours. When prolyl-amino acid ester was used as the starting material, 1 to 2 M acetic acid was the most effective concentration.

  当二肽酯在含有0.1 M醋酸的2-丁醇中回流3小时时，得到了光学纯的二酮哌嗪，产率良好。当使用脯氨酰氨基酸酯作为起始材料时，1至2 M醋酸是最有效的浓度。
• Chiral relay auxiliary for the synthesis of enantiomerically pure α-amino acids
  作者：Steven D. Bull、Stephen G. Davies、Simon W. Epstein、Jacqueline V. A. Ouzman

  DOI：10.1039/a800407b

  日期：——

  Chiral auxiliary (3S)-N,N′-bis(p-methoxybenzyl)-3-isopropylpiperazine-2,5-dione employs a chiral relay network based on non-stereogenic N-benzyl protecting groups to enhance diastereocontrol during enolate alkylation.

  手性辅助剂（3S）-N,N′-双（对甲氧基苄基）-3-异丙基哌嗪-2,5-二酮利用基于非立体中心的N-苄基保护基团的手性中继网络，以增强酮酸酯烷基化过程中的非对映选择性控制。
• 15N NMR spectroscopy. 19—spectroscopic characterization of cyclodipeptides (2,5-dioxopiperazines)
  作者：Hans R. Kricheldorf

  DOI：10.1002/mrc.1270130111

  日期：1980.1

  AbstractVarious cyclodipeptides containing glycine, alanine, leucine, valine, phenylalanine, phenylglycine and sarcosine units were synthesized by cyclization of dipeptide pentachlorophenyl esters. The 13C and natural abundance 15N NMR spectra of these heterocycles were measured in trifluoroacetic acid and compared with the spectra of the corresponding amino acids and polypeptides. The 13C NMR carbonyl signals of all cyclodipeptides show a 1.5–4.0 ppm upfield shift relative to the corresponding polypeptides. The 15N NMR signals show no such consistent relationship. The substituent effects and the neighbouring residue effects observed in the 15N NMR spectra of the cyclodipeptides are different from those of polypeptides, while the one bond NH coupling constant of cis and trans amide groups was almost identical. The nitrogen and the carbonyl signal of the Gly units in cyclo‐Gly‐Phe show an extraordinary downfield shift, reflecting the interaction of the phenyl group with the 2,5‐dioxopiperazine ring.
• A chiral relay auxiliary for the synthesis of homochiral α-amino acids
  作者：Steven D. Bull、Stephen G. Davies、Simon W. Epstein、Michael A. Leech、Jacqueline V. A. Ouzman

  DOI：10.1039/a803124j

  日期：——

  A new chiral auxiliary (3S)-N,N′-bis(p-methoxybenzyl)-3-isopropylpiperazine-2,5-dione 7 has been developed for the asymmetric synthesis of α-amino acids. The auxiliary 7 employs a novel chiral relay network based on non-stereogenic N-benzyl protecting groups which enhance the diastereoselectivity observed during alkylation of its C6 enolate 25.

  我们开发了一种新的手性辅助剂 (3S)-N,Nâ²-双（对甲氧基苄基）-3-异丙基哌嗪-2,5-二酮 7，用于δ-氨基酸的不对称合成。辅助剂 7 采用了一种基于非固有 N-苄基保护基团的新型手性中继网络，从而提高了其 C6 对映体 25 烷基化过程中观察到的非对映选择性。