(Z)-1-acetyl-3-(3-methoxy-benzylidene)-piperazine-2,5-dione | 151692-02-3

• 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: (Z)-1-acetyl-3-(3-methoxy-benzylidene)-piperazine-2,5-dione
• 英文别名: 1-acetyl-3-(3-methoxybenzylidene)piperazine-2,5-dione；(3Z)-1-acetyl-3-[(3-methoxyphenyl)methylidene]piperazine-2,5-dione
• CAS: 151692-02-3
• 化学式: C₁₄H₁₄N₂O₄
• 分子量: 274.276
• InChiKey: NFWYGOOFSWOKGU-GHXNOFRVSA-N

物化性质

• 熔点：
  199-200 °C
• 沸点：
  580.7±50.0 °C(Predicted)
• 密度：
  1.308±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  75.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-1-acetyl-3-(3-methoxy-benzylidene)-piperazine-2,5-dione 在 盐酸 、 水 作用下， 反应 4.0h， 以80%的产率得到3-(3-Methoxyphenyl)-2-oxopropansaeure
  参考文献：
  名称：

  Novel approach to the synthesis of aliphatic and aromatic α-keto acids

  摘要：

  A new practical and efficient synthesis of alpha-keto acids was accomplished starting from the synthon 1,4-diacetylpiperazine-2,5-dione. The synthesis encompasses both aromatic and aliphatic substrates proving to be versatile and innovative with excellent carbon economy and recycling of the glycine by-product. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.06.078
• 作为产物：
  描述：

  1,4-二乙酰基哌嗪-2,5-二酮 、 3-甲氧基苯甲醛 在 potassium tert-butylate 作用下， 以 二氯甲烷 、 叔丁醇 为溶剂， 反应 3.0h， 以92%的产率得到(Z)-1-acetyl-3-(3-methoxy-benzylidene)-piperazine-2,5-dione
  参考文献：
  名称：

  Novel approach to the synthesis of aliphatic and aromatic α-keto acids

  摘要：

  A new practical and efficient synthesis of alpha-keto acids was accomplished starting from the synthon 1,4-diacetylpiperazine-2,5-dione. The synthesis encompasses both aromatic and aliphatic substrates proving to be versatile and innovative with excellent carbon economy and recycling of the glycine by-product. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.06.078

文献信息

• AROYL-PIPERAZINE DERIVATIVES, THEIR PREPARATION AND THEIR USE AS TACHYKININ ANTAGONISTS
  申请人：——

  公开号：US20030114668A1

  公开（公告）日：2003-06-19

  This invention relates to piperazine derivatives of formula (I), wherein Y is bond or lower alkylene, R1 is aryl which may have substituent(s), R2 is aryl or indolyl, each of which may have substituent(s), R3 is hydrogen or lower alkyl, and R4 is as defined in the description, and its pharmaceutically acceptable salt, to processes for preparation thereof, to pharmaceutical composition comprising the same, and to a use of the same for treating or preventing Tachykinin-mediated diseases in human beings or animals. 1

  本发明涉及式(I)的哌嗪衍生物，其中Y是键或低级烷基，R1是可能含有取代基的芳基，R2是芳基或吲哚基，其中每个都可能含有取代基，R3是氢或低级烷基，R4如描述中定义，以及其药用可接受的盐，其制备过程，包含该化合物的药物组合物，以及用于治疗或预防人类或动物中速激肽介导的疾病的用途。
• Aroyl-piperazine derivatives, their preparation and their use as tachykinin antagonists
  申请人：Miyake Hiroshi

  公开号：US20050027121A1

  公开（公告）日：2005-02-03

  This invention relates to piperazine derivatives of the formula: wherein each symbol is as defined in the description, and its pharmaceutically acceptable salt, to processes for preparation thereof, to pharmaceutical composition comprising the same, and to a use of the same for treating or preventing Tachykinin-mediated diseases in human being or animals.

  本发明涉及以下式子的哌嗪衍生物：其中每个符号如描述中定义的那样，并且其药学上可接受的盐，用于其制备的过程，包括相同的制药组合物，以及用于治疗或预防人类或动物的Tachykinin介导疾病的用途。
• Hemipiperazines as peptide-derived molecular photoswitches with low-nanomolar cytotoxicity
  作者：Susanne Kirchner、Anna-Lena Leistner、Peter Gödtel、Angelika Seliwjorstow、Sven Weber、Johannes Karcher、Martin Nieger、Zbigniew Pianowski

  DOI：10.1038/s41467-022-33750-7

  日期：——

  Molecular photoswitches transform light energy into reversible structural changes. Their combination with known pharmacophores often allows for photomodulation of the biological activity. The effort to apply such compounds in photopharmacology as light-activated pro-drugs is, however, hampered by serious activity reduction upon pharmacophore modifications, or limited biostability. Here we report that

  分子光电开关将光能转化为可逆的结构变化。它们与已知药效团的结合通常允许对生物活性进行光调制。然而，将此类化合物作为光激活前药应用于光药理学的努力受到药效团修饰后活性严重降低或生物稳定性有限的阻碍。在这里，我们报告一种有效的抗有丝分裂剂普那布林及其衍生物表现出高达 56 倍的可逆活性光调制。或者，用青光进行不可逆的光激活可以将细胞毒性提高三个数量级——所有这些都不会影响原来的活性水平，因为原来的药效团结构没有改变。这是由于普那布林支架内存在肽衍生的光开关基序半哌嗪所致。此外，我们系统地描述了这些热稳定和生物相容性半哌嗪的光致变色，以及来自普那布林的光可切换荧光团。后者可能进一步扩大半哌嗪光致变色对超分辨率显微镜的适用性。
• Improvements in Aldol Reactions with Diketopiperazines
  作者：Juan Francisco González、Elena de la Cuesta、Carmen Avendaño

  DOI：10.1081/scc-120030746

  日期：2004.12.31

  Precipitation of products by using dichloromethane as solvent permits an efficient aldol-type reaction between 1,4-diacetyl-2,5-piperazinedione and aromatic aldehydes catalyzed by K'BuO/'BuOH independently of the electrophilic character of the aryl ring. A simple method to obtain 3-methyl-2,4,5-trimethoxybenzaldehyde is also reported.
• Peters, David A.; Beddoes, Roy L.; Joule, John A., Journal of the Chemical Society. Perkin transactions I, 1993, # 11, p. 1217 - 1224
  作者：Peters, David A.、Beddoes, Roy L.、Joule, John A.

  DOI：——

  日期：——