(+/-)-trans-3,6-dibenzylpiperazine-2,5-dione | 374674-82-5

• 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: (+/-)-trans-3,6-dibenzylpiperazine-2,5-dione
• 英文别名: (3R,6S)-3,6-dibenzylpiperazine-2,5-dione；trans-3,6-Dibenzyl-2,5-piperazindion
• CAS: 374674-82-5
• 化学式: C₁₈H₁₈N₂O₂
• 分子量: 294.353
• InChiKey: JUAPMRSLDANLAS-IYBDPMFKSA-N

物化性质

• 沸点：
  594.2±43.0 °C(Predicted)
• 密度：
  1.186±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  (+/-)-trans-3,6-dibenzylpiperazine-2,5-dione 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 (2S,5R)-2,5-dibenzylpiperazine
  参考文献：
  名称：

  Novel chiral N,N′-dimethyl-1,4-piperazines with metal binding abilities

  摘要：

  With the objective of developing novel chiral ligands, we report an efficient strategy to prepare chiral N,N-dimethyl-1,4-piperazines, six-member heterocyclic molecules that possess metal binding features. We prepared and characterized 18 piperazines, and evaluated their ability to complex different mono- and divalent metals, using a rapid picrate extraction technique. Some newly prepared diamine ligands were used in diethylzinc alkylation of aryl aldehydes. Yields increased significantly in the presence of the diamine ligands, though enantioselectivity was low. The results demonstrate the validity of the approach for preparing and identifying useful chiral diamine ligands. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.08.051
• 作为产物：
  描述：

  Boc-D-苯丙氨酸 在 甲酸 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (+/-)-trans-3,6-dibenzylpiperazine-2,5-dione
  参考文献：
  名称：

  Synthesis of a reported calpain inhibitor isolated from Streptomyces griseus

  摘要：

  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.

  DOI：

  10.1016/s0960-894x(01)00524-8

文献信息

• Heterogeneous Catalytic Hydrogenation of Chiral Amino Acid Methyl Esters to Amino Alcohols with Retention of Configuration Over Mg-Modified Cu/ZnO/Al2O3 Catalyst
  作者：Bing Zhan、Shuangshuang Zhang、Jun Yu、Xiuzheng Xiao、Xiaoming Guo、Dongsen Mao、Guanzhong Lu

  DOI：10.1007/s10562-017-2116-3

  日期：2017.8

  hydrogenation of amino acid methyl esters to chiral amino alcohols is an important and fascinating process. The CuZn0.3Mg0.1AlOx catalyst for the synthesis of chiral amino alcohols was prepared by the fractional co-precipitation method in the 50–100 g scale. The effect of the reduction gas on the catalytic activity, and the effects of the reaction conditions (R-p-m/Cat, temperature, reaction time, H2 pressure

  将氨基酸甲酯选择性氢化为手性氨基醇是一个重要且引人入胜的过程。用于合成手性氨基醇的 CuZn0.3Mg0.1AlOx 催化剂是通过分级共沉淀法以 50-100 g 的规模制备的。考察了还原气体对催化活性的影响，以及反应条件（Rpm/Cat、温度、反应时间、H2压力和溶剂）对R-苯基甘氨酸甲酯催化加氢反应（记为Rpm）的影响. 当 Rpm 在乙醇溶剂中在 5 MPa 的 H2 和 80°C 下在该被 H2 还原的催化剂上加氢 10 小时时，获得了 87.7% 的产率，具有~100% ee 值的 R-苯基甘氨醇，其反应活化能（Ea ) 为 36.7 kJ/mol。重复使用16次后，其催化活性几乎没有变化。
• Engineered transaminopeptidase, aminolysin-S for catalysis of peptide bond formation to give linear and cyclic dipeptides by one-pot reaction
  作者：Hirokazu Usuki、Yoshiko Uesugi、Jiro Arima、Yukihiro Yamamoto、Masaki Iwabuchi、Tadashi Hatanaka

  DOI：10.1039/b914320c

  日期：——

  Aminopeptidase from Streptomyces thermocyaneoviolaceus NBRC14271 was engineered into transaminopeptidase and used to catalyze an aminolysis reaction to give linear and cyclic dipeptides from cost-effective substrates such as the ester derivatives of amino acids.

  将来自热链霉菌NBRC14271的氨肽酶工程化为转氨肽酶，并用于催化氨解反应，以从成本有效的底物（例如氨基酸的酯衍生物）得到线性和环状的二肽。
• Pyrazine chemistry. II. Reduction of 3,6-Dibenzylidenepiperazine-2,5-diones
  作者：SM Marcuccio、JA Elix

  DOI：10.1071/ch9841791

  日期：——

  A reinvestigation of the reduction of 3,6-dibenzylidenepiperazine-2,5-dione (1) with zinc and acetic acid established that this reaction gave (Z)-6-benzyl-3-benzylidenepiperazine-2,5-dione (10). When a mixture of acetic acid and hydrochloric acid was used in the reduction, a mixture of trans- (12) and cis-3,6-dibenzylpiperazine-2,5-dione (5) was obtained. Direct catalytic reduction of 3,6-di(2-chloro- benzy1idene)piperazine-2,5-dione (2) to (�)-cis-3,6-di(2-chlorobenzyl)piperazine-2,5-dione (6) was also accomplished.

  对锌和乙酸还原 3,6-二苄基亚哌嗪-2,5-二酮 锌和乙酸还原 3,6-二苄基亚哌嗪-2,5-二酮 (1) 确定该反应生成了 (Z)-6-苄基-3-亚苄基哌嗪-2,5-二酮 (10)。当使用乙酸和盐酸的混合物 酸和盐酸的混合物进行还原时，可得到反式 (12) 和顺式-3,6-二苄基哌嗪-2,5-二酮 (5) 的混合物。直接 催化还原 3,6-二(2-氯亚苄基)哌嗪-2,5-二酮(2)至(......)。 (�)-顺式-3,6-二(2-氯苄基)哌嗪-2,5-二酮(6)。 (6)。
• 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。
• Solid‐state synthesis of cyclo LD‐diphenylalanine: A chiral phase built from achiral subunits
  作者：Ariel Pérez‐Mellor、Katia Le Barbu‐Debus、Anne Zehnacker

  DOI：10.1002/chir.23195

  日期：2020.5

  The solid‐state structure of LL/DD or LD/DL diphenylalanine diluted in KBr pellets is studied by infrared (IR) absorption and vibrational circular dichroism (VCD) spectroscopy. The structure depends on the absolute configuration of the residues. The natural LL diphenylalanine exists as a mixture of neutral and zwitterionic structures, depending on the humidity of the sample, while mostly the zwitterion

  通过红外（IR）吸收和振动圆二色性（VCD）光谱研究了稀释在KBr颗粒中的LL / DD或LD / DL二苯丙氨酸的固态结构。结构取决于残基的绝对构型。天然LL二苯丙氨酸以中性和两性离子结构的混合物形式存在，具体取决于样品的湿度，而无论实验条件如何，LD二苯丙氨酸的两性离子大部分都被观察到。该体系在125°C加热时会自发环化，从而形成唯一的产物二酮哌嗪（DKP）二肽。LD的反应比LL的二苯丙氨酸更快。如所期望的，LL和DD二苯丙氨酸反应形成环二苯丙氨酸的LL和DD对映异构体。有趣的是 由LD或DL二苯丙氨酸形成的DKP二肽显示出意外的光学活性，由LD和DL试剂形成的产物具有相反的VCD光谱。用晶体内单体之间的手性同步来解释，这保持了试剂的对称性，导致形成了由瞬时手性分子制成的新手性相。