(S)-3-[(Z)-benzylidene]hexahydropyrrolo[1,2-a]pyrazine-1,4-dione | 214849-88-4

• 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: (S)-3-[(Z)-benzylidene]hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
• 英文别名: (3Z,8aS)-3-benzylidene-6,7,8,8a-tetrahydropyrrolo[1,2-a]pyrazine-1,4-dione
• CAS: 214849-88-4
• 化学式: C₁₄H₁₄N₂O₂
• 分子量: 242.277
• InChiKey: QNHNSZPWSAZCLD-MMRAYRKESA-N

物化性质

• 沸点：
  574.207±50.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.303±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-3-[(Z)-benzylidene]hexahydropyrrolo[1,2-a]pyrazine-1,4-dione 在 palladium on activated charcoal 氢气 作用下， 生成 环(Phe-Pro)
  参考文献：
  名称：

  What is the structure of barettin? Novel synthesis of unsaturated diketopiperazines.

  摘要：

  DOI：

  10.1016/s0040-4039(00)96483-9
• 作为产物：
  描述：

  L-脯氨酸苄酯 在 ammonium acetate 、 溶剂黄146 、 N,N'-二异丙基碳二亚胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 (S)-3-[(Z)-benzylidene]hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
  参考文献：
  名称：

  Rational design and synthesis of unsaturated 2,5-dioxopiperazine derivatives as potential protein tyrosine kinase inhibitors

  摘要：

  The first general method for the synthesis of a library of trifunctionalized (Z)-3-alkylidene-2,5-piperazinediones as potential protein tyrosine kinase inhibitors from commercially available amino compounds, alpha-keto acids and aldehydes using a novel cyclization/cleavage strategy on solid support is described. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01599-8

文献信息

• Total Synthesis of Spirotryprostatins through Organomediated Intramolecular Umpolung Cyclization
  作者：Yong-Kai Xi、Hongbin Zhang、Rui-Xi Li、Shi-Yuan Kang、Jin Li、Yan Li

  DOI：10.1002/chem.201806411

  日期：2019.2.26

  reports a new method for the synthesis of biologically important DKP scaffolds based on an intramolecular nucleophilic α‐addition of general amides towards an alkynamide system. The utility of this umpolung cyclization mediated by trimethyl phosphine and l‐glutamic acid is highlighted by its application to the concise total syntheses of 6‐methoxyspirotryprostatin B (the first total synthesis), spirotryprostatin A

  环二肽2,5-二酮哌嗪（DKP）是药物和天然生物碱中的特权结构单元。这项工作报告了一种新的合成重要生物学DKP支架的方法，该方法基于一般酰胺的分子内亲核α加成到炔酰胺系统。由三甲基膦和l-谷氨酸介导的这种蛋白环环化的实用性通过将其应用于简明的6-甲氧基spirotryprostatin B（首次合成），spirotryprostatin A和spirotryprostatin B的简明总合成中而得到了应用。
• Intermolecular and Intramolecular Diels−Alder Cycloadditions of 3-Ylidenepiperazine-2,5-diones and 5-Acyloxy-2(1<i>H</i>)-pyrazinones
  作者：Shangde Jin、Pablo Wessig、Jürgen Liebscher

  DOI：10.1021/jo0100897

  日期：2001.6.1

  Diels-Alder reactions of alkenes and alkynes to the piperazine ring, under acidic conditions or in the presence of acetyl chloride, to afford tricyclic piperazine-2,5-diones 19, 20, 23-25, 27, 44, and 45. Intramolecular cycloadditions occur if 3-ylidenepiperazine-2,5-diones 30 and 32 are used as the starting materials. This procedure is a convenient path to bridged bicyclo[2.2.2]diazaoctane ring systems such

  3-亚烷基哌嗪-2,5-二酮16和39和5-酰氧基-2（1H）-吡嗪酮17可以用作烯烃和炔烃在酸性条件下或在酸性条件下Diels-Alder反应的原料。存在乙酰氯，得到三环哌嗪-2,5-二酮19、20、23-25、27、44和45。如果使用3-亚苯基哌嗪-2,5-二酮30和32作为分子，则发生分子内环加成。起始材料。此程序是连接双环[2.2.2]二氮辛烷环系统（例如31和33）的便捷途径，前者存在于具有生物活性的二次霉菌代谢产物中，例如VM55599（1）或brevianamide A（5）。从各种真菌中分离出来。吲哚化合物31的合成为拟议的以Diels-Alder反应为关键步骤的生化途径提供了证据。
• Unusual CC Bond Migration in 3-Ylidene-2,5-piperazinediones
  作者：Shangde Jin、Pablo Wessig、Jürgen Liebscher

  DOI：10.1002/(sici)1099-0690(200005)2000:10<1993::aid-ejoc1993>3.0.co;2-i

  日期：2000.5

  Treatment of 3-alkylidene or 3-benzylidene-2,5-piperazinediones 6 with catalytic amounts of acid gives rise to the formation of isomers 7 by migration of the CC bond into the alkyl substituent at position 6, or results in mixtures of racemic 7 and E isomers 8. The existence of tautomeric equilibria is discussed.

  用催化量的酸处理 3-亚烷基或 3-亚苄基-2,5-哌嗪二酮 6，通过 CC 键迁移到 6 位的烷基取代基中形成异构体 7，或导致外消旋体 7 的混合物和 E 异构体 8. 讨论了互变异构平衡的存在。
• Stereoselective Epoxidation and Bromoalkoxylation with 3-Ylidenepyrazine-2,5-diones
  作者：Jürgen Liebscher、Annett Bartels、Peter G. Jones

  DOI：10.1055/s-2003-36259

  日期：——

  were stereoselectively epoxidsed by dimethyldioxirane giving access to spirooxiranes 2 and diols 3. Bromohydroxylation and bromoalkoxylation of 3-ylidenepyrazine-2,5-diones 1 produced high yields of optically active 3-(1-bromoalkyl)pyrazine-2,5-diones 4 with a 3-hydroxy or 3-alkoxy function, respectively. Whereas direct hydrogenation of epoxides 2 afforded epimeric mixtures of 3-( 1-hydroxyalkyl)pyrazine-2

  3-Ylidenepyrazine-2,5-diones 1 被二甲基二环氧乙烷立体选择性环氧化，得到螺环氧乙烷 2 和二醇 3。 3-ylidenepyrazine-2,5-diones 1 的溴羟基化和溴烷氧基化产生高产率的光学活性 3-(1-bromoalkyl) )pyrazine-2,5-diones 4 分别具有 3-羟基或 3-烷氧基官能团。虽然环氧化物 2 的直接氢化提供了 3-(1-羟基烷基)吡嗪-2,5-二酮 5 和 6 的差向异构体混合物，但通过环氧乙烷环的伯酸裂解随后氢化所得的氢化可高度立体选择性地转化为 5酮-烯醇混合物 7/8。
• [FR] ADJUVANTS AGROCHIMIQUES<br/>[EN] AGROCHEMICAL ADJUVANTS
  申请人：[en]CRODA INTERNATIONAL PLC

  公开号：WO2022040038A2

  公开（公告）日：2022-02-24

  A novel agrochemical formulation comprising adjuvants selected from diketopiperazines and an agrochemical active. A concentrate is also provided suitable for forming the formulation. The diketopiperazine provide adjuvancy in the concentrate and agrochemical formulations. There is also provided a method of making the formulation, and use of said diketopiperazines as adjuvants in agrochemical formulations is also provided. A method of obtaining the diketopiperazines from culturing ofMetarhizium carneum, strain RKD0578 is also described. The extracted diketopiperazines may be used in a formulation for treating vegetation to control pests, or seed coating. Alternatively the strain RKD0578 itself may be used in a seed coating or in a formulation for treating vegetation to control pests.