(S)-1-乙酰基-2-吡咯烷酮-5-羧酸 | 56805-18-6

• 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: (S)-1-乙酰基-2-吡咯烷酮-5-羧酸
• 英文名称: N-acetyl-L-pyroglutamic acid
• 英文别名: N-acetyl-(S)-pyroglutamic acid；S-1-acetylpyroglutamic acid；(S)-1-acetyl-2-pyrrolidone-5-carboxylic acid；(S)-1-acetyl-5-oxopyrrolidine-2-carboxylic acid；1-acetyl-5-oxo-L-proline；1-Acetyl-5-oxo-L-prolin；L-1-Acetyl-5-oxoproline；(2S)-1-acetyl-5-oxopyrrolidine-2-carboxylic acid
• CAS: 56805-18-6
• 化学式: C₇H₉NO₄
• 分子量: 171.153
• InChiKey: AYNBBSMJRSAAHP-YFKPBYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  74.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-1-乙酰基-2-吡咯烷酮-5-羧酸 在 ammonium hydroxide 、 氯化亚砜 、 silver(l) oxide 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 2.92h， 生成 methyl (S)-5-oxo-2-pyrrolidineacetate
  参考文献：
  名称：

  Synthesis of 2-Oxa and 2-Aza Analogs of Pyrrolizidine-3,5-diones (Lukes-Sorm Dilactam)

  摘要：

  The synthesis of 2-oxa and 2-aza analogs of pyrrolizidine-3,5-dione (Lukes-Sorm dilactam), which has amnesia reversal activity, is reported. Optically active (+)-2-oxa and (+)-2-aza analogs [(+)-2 and (+)-3] and racemic 2-aza analog and its 1-methoxycarbonyl derivatives [(+)-3 and (+)-13 and -14] were prepared from (-)-S-pyroglutamic acid and succinimide, respectively.

  DOI：

  10.3987/com-91-s56
• 作为产物：
  描述：

  acetic S-1-acetylpyroglutamic anhydride 在 水 作用下， 反应 2.0h， 以92%的产率得到(S)-1-乙酰基-2-吡咯烷酮-5-羧酸
  参考文献：
  名称：

  Synthesis of 2-Oxa and 2-Aza Analogs of Pyrrolizidine-3,5-diones (Lukes-Sorm Dilactam)

  摘要：

  The synthesis of 2-oxa and 2-aza analogs of pyrrolizidine-3,5-dione (Lukes-Sorm dilactam), which has amnesia reversal activity, is reported. Optically active (+)-2-oxa and (+)-2-aza analogs [(+)-2 and (+)-3] and racemic 2-aza analog and its 1-methoxycarbonyl derivatives [(+)-3 and (+)-13 and -14] were prepared from (-)-S-pyroglutamic acid and succinimide, respectively.

  DOI：

  10.3987/com-91-s56

文献信息

• Sequential Acylation/Silylation/Hetero‐Claisen Rearrangement of Nitroalkanes for the Synthesis of Protected Hydroxyoxime Derivatives
  作者：Yulia A. Antonova、Sema L. Ioffe、Alexey Yu. Sukhorukov、Andrey A. Tabolin

  DOI：10.1002/ejoc.202100469

  日期：2021.6.14

  One-pot acylation-silylation sequence was developed for the synthesis of protected hydroxyoximes from aliphatic nitro compounds. Procedure is characterized by wide substrate scope for nitro compounds, acylating and silylating agents.

  开发了一锅酰化-甲硅烷基化序列，用于从脂肪族硝基化合物合成受保护的羟基肟。该程序的特点是硝基化合物、酰化剂和甲硅烷基化剂的底物范围广泛。
• The Forgotten Pyrazines: Exploring the Dakin–West Reaction
  作者：Martien A. Würdemann、Cristina Niţu、Stefaan M. A. De Wildeman、Katrien V. Bernaerts、Romano V. A. Orru

  DOI：10.1002/chem.202000475

  日期：2020.6.26

  Pyrazines are an underreported class of N‐heterocycles available from nitrogen‐rich biomass presenting an interesting functional alternative for current aromatics. In this work, access to pyrazines obtained from amino acids by using the 90 year old Dakin–West reaction was explored. After a qualitative screening several functional proteinogenic amino acids proved good substrates for this reaction, which

  吡嗪类化合物是一种报道较少的N杂环类化合物，可从富氮生物质中获得，为当前的芳族化合物提供了有趣的功能替代品。在这项工作中，探索了使用90年的Dakin-West反应从氨基酸获得的吡嗪的途径。经过定性筛选后，几种功能性蛋白原氨基酸被证明是该反应的良好底物，已成功地按比例缩放至相应的中间体α-乙酰氨基酮的克数合成。随后，优化了使用δ-氨基乙酰丙酸形成吡嗪的条件，并利用这些条件合成了一组相关的五种高纯度的功能性二甲基吡嗪。这些吡嗪被认为是适用于广泛应用的芳香族结构单元的多功能工具箱，
• Tricyclic sulfones as RORγ modulators
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：US10273259B2

  公开（公告）日：2019-04-30

  There are described RORγ modulators of the formula (I), and formula (II) or stereoisomers, tautomers, pharmaceutically acceptable salts, solvates, or prodrugs thereof, wherein all substituents are defined herein. Also provided are pharmaceutical compositions comprising the same. Such compounds and compositions are useful in methods for modulating RORγ activity in a cell and methods for treating a subject suffering from a disease or disorder in which the subject would therapeutically benefit from modulation of RORγ activity, for example, autoimmune and/or inflammatory disorders.

  描述了式 (I) 的 RORγ 调节剂、 和式(II) 或其立体异构体、同系物、药学上可接受的盐、溶液或原药，其中所有取代基均在本文中定义。还提供了包含上述化合物的药物组合物。此类化合物和组合物可用于调节细胞中RORγ活性的方法和治疗患有疾病或失调的受试者的方法，其中受试者将从调节RORγ活性中获得治疗益处，例如自身免疫和/或炎症性失调。
• N-acetylamino acids, related N-acetyl compounds and their topical use
  申请人：——

  公开号：US20030198656A1

  公开（公告）日：2003-10-23

  Compositions comprising N-acetylamino acids and/or related N-acetyl compounds are useful to alleviate or improve various cosmetic conditions and dermatological disorders, including changes or damage to skin, nail and hair associated with intrinsic aging and/or extrinsic aging, as well as changes or damage caused by extrinsic factors. The N-acetylamino acid and/or related N-acetyl compound composition may further comprise a cosmetic, pharmaceutical or other topical agent to enhance or create synergetic effects.

  由 N-乙酰基氨基酸和/或相关 N-乙酰基化合物组成的组合物可用于缓解或改善各种美容状况和皮肤病，包括与内在老化和/或外在老化相关的皮肤、指甲和头发的变化或损伤，以及由外在因素引起的变化或损伤。N-acetylamino acid 和/或相关 N-acetyl 化合物组合物可进一步包含化妆品、药物或其他外用制剂，以增强或产生协同效应。
• N-acetyl cysteine and its topical use
  申请人：——

  公开号：US20030229141A1

  公开（公告）日：2003-12-11

  Methods to alleviate or improve various cosmetic conditions and dermatological disorders, including changes or damage to skin, nail and hair associated with intrinsic aging and/or extrinsic aging, as well as changes or damage caused by extrinsic factors using compositions comprising N-acetyl-cysteine (isomeric or non-isomeric forms) and/or free acid, salt, lactone, amide or ester forms of N-acetyl-cysteine are described. The methods provided may also comprise application of a composition further containing various cosmetic, pharmaceutical or other topical agents to enhance or create synergetic effects.

  本文描述了使用包含 N-乙酰-半胱氨酸（异构体或非异构体形式）和/或 N-乙酰-半胱氨酸的游离酸、盐、内酯、酰胺或酯形式的组合物来缓解或改善各种美容状况和皮肤病的方法，包括与内在老化和/或外在老化相关的皮肤、指甲和头发的变化或损伤，以及外在因素引起的变化或损伤。所提供的方法还可包括使用进一步含有各种化妆品、药物或其他外用制剂的组合物，以增强或产生协同效应。