cyclo-L-N-methylphenylalanyl-D-N-methylphenylalanyl | 61139-44-4

• 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: cyclo-L-N-methylphenylalanyl-D-N-methylphenylalanyl
• 英文别名: trans-3,6-dibenzyl-1,4-dimethylpiperazine-2,5-dione；(3R,6S)-3,6-dibenzyl-1,4-dimethylpiperazine-2,5-dione
• CAS: 61139-44-4；374674-79-0
• 化学式: C₂₀H₂₂N₂O₂
• 分子量: 322.407
• InChiKey: KNKXKVUFAHAVOL-HDICACEKSA-N

物化性质

• 熔点：
  188-189 °C
• 沸点：
  534.6±43.0 °C(Predicted)
• 密度：
  1.159±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  cyclo-L-N-methylphenylalanyl-D-N-methylphenylalanyl 在 二苯甲酮 作用下， 以 乙酸乙酯 为溶剂， 反应 672.0h， 以80%的产率得到1,4-dimethyl-2-benzylpiperazine-3,5,6-trione
  参考文献：
  名称：

  Marcuccio, Sebastian M.; Elix, John A., Australian Journal of Chemistry, 1985, vol. 38, # 2, p. 343 - 346

  摘要：

  DOI：
• 作为产物：
  描述：

  (S,Z)-3-benzyl-6-benzylidene-1,4-dimethylpiperazine-2,5-dione 以3%的产率得到
  参考文献：
  名称：

  TAKEUCHI, SEIJI;OHGO, YOSHIAKI;MIYOSHI, NORIKAZU;SHIN, CHUNG-GI;YONEZAWA,+, HETEROCYCLES, 31,(1990) N1, C. 2073-2078

  摘要：

  DOI：

文献信息

• Pyrazine chemistry. III. Synthesis and stereochemistry of 1,4-Dimethyl and 1,4-Diacetyl derivatives of 3,6-Dibenzylpiperazine-2,5-dione
  作者：SM Marcuccio、JA Elix

  DOI：10.1071/ch9842397

  日期：——

  The trans- and (�) cis-isomers of 1,4-dimethyl-and 1,4-diacetyl-3,6-dibenzylpiperazine-2,5-dione were synthesized. The hydriodic acid reduction of 3,6-dibenzylidene-1,4-dimethylpiperazine-2,5-dione gave (�)-cis-3,6-dibenzyl-1,4-dimethylpiperazine-2,5-dione although this product has previously been assigned the trans-geometry. The unknown isolated from the permanganate oxidation of (�)-cis- 1,4-diacetyl-3,6-dibenzylpiperazine-2,5- has been identified as the corresponding trans-isomer.

  合成了 1,4-二甲基和 1,4-二乙酰基-3,6-二苄基哌嗪-2,5-二酮的反式和顺式异构体。 合成了 1,4-二甲基和 1,4-二乙酰基-3,6-二苄基哌嗪-2,5-二酮的反式和顺式异构体。通过氢碘酸还原 得到了(�)-顺式-3,6-二苄基-1,4-二甲基哌嗪-2,5-二酮。 尽管该产物之前被指定为反式。从高锰酸盐 从(�)-顺式-1,4-二乙酰基-3,6-二苄基哌嗪-2,5-二酮的高锰酸盐氧化反应中分离出的未知物已被确定为相应的反式异构体。 反式异构体。
• Synthesis of a reported calpain inhibitor isolated from Streptomyces griseus
  作者：I.O Donkor、M.Lee Sanders

  DOI：10.1016/s0960-894x(01)00524-8

  日期：2001.10

  The reported diketopiperazine calpain inhibitor, cis-L-L-3.6-bis-(4-hydroxybenzyl)-1,4-dimethylpiperazine-2,5-dione 1, and its analogues 3 and 4 were synthesized from the corresponding amino acids. The previously assigned structure of 1 is confirmed but neither synthetic 1 nor its N-methylphenylalanine analogues 3 and 4 inhibit porcine erythrocyte calpain I. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Catalytic Hydrogenation of 2,5-Dialkylpyrazines and 3,6-Dialkyl-2-hydroxypyrazines
  作者：Akihiro Ohta、Yukari Okuwaki、Tsuyoshi Komaru、Mieko Hisatome、Yasushi Yoshida、Jun Aizawa、Yumi Nakano、Hiroko Shibata、Takuya Miyazaki、Tokuhiro Watanabe

  DOI：10.3987/r-1987-10-2691

  日期：——
• Asymmetric Synthesis of a Piperazine Alkaloid
  作者：Seiji Takeuchi、Yoshiaki Ohgo、Norikazu Miyoshi、Chung-gi Shin、Yasuchika Yonezawa

  DOI：10.3987/com-90-5573

  日期：——

  A piperazine alkaloid, (2S,5S)-2,5-dibenzyl-1,4-dimethylpiperazine, was synthesized by reduction of (3S,6S)-3,6-dibenzyl-1,4-dimethyl-2,5-piperazinedione which was prepared by a catalytic asymmetric hydrogenation of the corresponding 3,6-dibenzylidene derivative.
• Conformations of six N-methylated diketopiperazines in solution
  作者：W. Radding、B. Donzel、N. Ueyama、M. Goodman

  DOI：10.1021/ja00539a004

  日期：1980.9