(3S)-1,3-二甲基-2,5-哌嗪二酮 | 62246-37-1

• 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
• 中文名称: (3S)-1,3-二甲基-2,5-哌嗪二酮
• 英文名称: (3S)-1,3-dimethylpiperazine-2,5-dione
• 英文别名: (3S)-1,3-dimethyl-2,5-piperazinedione；cyclo(sarcosine-L-alanine)
• CAS: 62246-37-1
• 化学式: C₆H₁₀N₂O₂
• 分子量: 142.158
• InChiKey: DKJXHTTVLDGGFA-BYPYZUCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933599090

反应信息

• 作为反应物：
  描述：

  (3S)-1,3-二甲基-2,5-哌嗪二酮 在 三丁基膦 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 19.25h， 生成 (4S)-2,4-dimethyl-2,4-dihydro-(1H)-pyrazino<2,1-b>quinazoline-3,6-dione
  参考文献：
  名称：

  Cledera, Pilar; Villacampa, Mercedes; Avendano, Carmen, ARKIVOC, 2011, vol. 2011, # 3, p. 72 - 98

  摘要：

  DOI：
• 作为产物：
  描述：

  [((S)-2-tert-Butoxycarbonylamino-propionyl)-methyl-amino]-acetic acid pentachlorophenyl ester 在 三氟乙酸 、 N,N-二乙基苯胺 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 2.0h， 生成 (3S)-1,3-二甲基-2,5-哌嗪二酮
  参考文献：
  名称：

  15N NMR spectroscopy. 19—spectroscopic characterization of cyclodipeptides (2,5-dioxopiperazines)

  摘要：

  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.

  DOI：

  10.1002/mrc.1270130111

文献信息

• Microwave-Assisted, Solvent-Free Synthesis of Several Quinazoline Alkaloid Frameworks
  作者：J. Menéndez、Pilar Cledera、Juan Sánchez、Esmeralda Caballero、Tamara Yates、Elena Ramírez、Carmen Avendaño、M. Ramos

  DOI：10.1055/s-2007-990818

  日期：2007.11

  Microwave irradiation leads to a considerable improvement of the cyclocondensation between anthranilic acid and lactim ethers derived from piperazine-2,5-diones in terms of reaction times, yields, and stereocenter integrity. This reaction has been used to prepare some derivatives of the pyrazino[2,1-b]quinazoline-3,6-dione system present in many quinazoline alkaloids. It could also be applied to the synthesis of compounds containing the complete hexacyclic ring system of the anti-MDR natural product N-acetyl­ardeemin, and other comprising the pentacyclic framework of circumdatin E. The microwave-assisted reaction was also much better than the thermal one when applied to a bis-lactim ether, leading to the corresponding pentacyclic pyrazino[2,1-b:5,4-b′]diquinazoline-8,16-dione in excellent yield.

  微波辐照显著改善了邻氨基苯甲酸与来自哌嗪-2,5-二酮的乳酰亚胺醚之间的环加成反应，在反应时间、产率和立体中心完整性方面均有显著提升。该反应已被用于制备多种喹唑啉生物碱中存在的吡嗪并[2,1-b]喹唑啉-3,6-二酮系统的衍生物。它还可以应用于合成含有抗多药耐药天然产物N-乙酰基阿德米宁的完整六环体系化合物，以及其他包含circumdatin E的五环框架的化合物。微波辅助反应在应用于双乳酰亚胺醚时也比热反应更为高效，得到了对应的五环吡嗪并[2,1-b:5,4-b′]双喹唑啉-8,16-二酮，产率极佳。
• [EN] 1-((S)-1-(3-CHLORO-5-FLUORO-2-((4-(1H-PYRAZOL-1-YL)-2-METHYLQUINOLIN-8-YLOXY)METHYL)PHENYL)ETHYL)-IMIDAZOLIDINE-2,4-DIONE DERIVATIVES AND RELATED COMPOUNDS AS BRADYKININ (BK) B2 RECEPTOR ANTAGONIST FOR TREATING SKIN DISEASES<br/>[FR] DÉRIVÉS DE 1-((S)-1-(3-CHLORO-5-FLUORO-2-((4-(1H-PYRAZOL-1-YL)-2-MÉTHYLQUINOLIN-8-YLOXY)MÉTHYL)PHÉNYL)ÉTHYL)-IMIDAZOLIDINE-2,4-DIONE ET COMPOSÉS APPARENTÉS SERVANT D'ANTAGONISTE DU RÉCEPTEUR B2 DE LA BRADYKININE (BK) POUR LE TRAITEMENT DE MALADIES DE LA PEAU
  申请人：PHARVARIS GMBH

  公开号：WO2020234479A1

  公开（公告）日：2020-11-26

  The invention relates to a compound according to general formula (I), which acts as a bradykinin (BK) B2 receptor antagonist; to a pharmaceutical composition containing one or more of the compound(s) of the invention; to a combination preparation containing at least one compound of the invention and at least one further active pharmaceutical ingredient; and to said compound(s) for use as in a method of treating a skin disorder; eye disease; ear disease; mouth, throat and respiratory disease; gastrointestinal disease; liver, gallbladder and pancreatic disease; urinary tract and kidney disease; disease of male genitale organs and female genitale organs; disease of the hormone system; metabolic disease; cardiovascular disease; blood disease; lymphatic disease; disorder of the central nervous system; brain disorder; musculoskeletal system disease; allergy disorder; pain; infectious disease; inflammatory disorder; injury; immunology disorder; cancer; hereditary disease; or edema. (I)

  该发明涉及一种符合一般式(I)的化合物，该化合物作为一种激肽酶B2（BK）受体拮抗剂；一种含有该发明化合物中的一个或多个化合物的药物组合物；一种含有至少一种该发明化合物和至少一种其他活性药物成分的联合制剂；以及用于治疗皮肤疾病、眼疾、耳疾、口腔、喉咙和呼吸道疾病、胃肠道疾病、肝脏、胆囊和胰腺疾病、泌尿道和肾脏疾病、男性生殖器官和女性生殖器官疾病、激素系统疾病、代谢性疾病、心血管疾病、血液疾病、淋巴疾病、中枢神经系统紊乱、脑部疾病、肌肉骨骼系统疾病、过敏疾病、疼痛、传染病、炎症性疾病、损伤、免疫学紊乱、癌症、遗传性疾病或水肿的方法中使用的该化合物。 (I)
• Cledera, Pilar; Villacampa, Mercedes; Avendano, Carmen, ARKIVOC, 2011, vol. 2011, # 3, p. 72 - 98
  作者：Cledera, Pilar、Villacampa, Mercedes、Avendano, Carmen、Menendez, J. Carlos

  DOI：——

  日期：——
• 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.