(3S,5S)-5-(hydroxymethyl)-3-methyl-2-pyrrolidinone | 138078-58-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (3S,5S)-5-(hydroxymethyl)-3-methyl-2-pyrrolidinone
• 英文别名: (3S,5S)-5-(hydroxymethyl)-3-methylpyrrolidin-2-one
• CAS: 138078-58-7
• 化学式: C₆H₁₁NO₂
• 分子量: 129.159
• InChiKey: RGDBSLYLHPZEME-WHFBIAKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2933790090

反应信息

• 作为反应物：
  描述：

  (3S,5S)-5-(hydroxymethyl)-3-methyl-2-pyrrolidinone 在 palladium on activated charcoal 4-二甲氨基吡啶 、 copper(I) bromide dimethylsulfide complex 、 氢气 、 三乙胺 作用下， 以 甲醇 、 乙二醇二甲醚 、 乙醚 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 46.5h， 生成 Trifluoro-acetic acid 5-[(2R,4S)-4-methyl-5-oxo-1-(2,2,2-trifluoro-acetyl)-pyrrolidin-2-yl]-pentyl ester
  参考文献：
  名称：

  Isolation, identification and determination of the absolute configuration of Fischerellin B. A new algicide from the freshwater cyanobacterium Fischerella muscicola (Thuret)

  摘要：

  A new 2-pyrrolidinone with a polyunsaturated side chain has been identified from the cyanobacterium Fischerella muscicola (Thuret). Its structure was elucidated by UV, NMR and mass spectroscopy. Derivatisation of the natural product and stereocontrolled synthesis of the derivative allowed the determination of the absolute configuration by means of chiral gas chromatography. The new compound, fischerellin B, shows algicidal properties. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0040-4039(96)02284-8
• 作为产物：
  描述：

  L-焦谷氨酸乙酯 在 锂硼氢 、 对甲苯磺酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 生成 (3S,5S)-5-(hydroxymethyl)-3-methyl-2-pyrrolidinone
  参考文献：
  名称：

  Anti-Beckwith stereoselectivity in amidyl radical cyclisations: Bu3SnH-mediated 5-exo-trig acyl mode cyclisation of 2-substituted pent-4-enamide radicals

  摘要：

  2-Substituted amidyl radicals derived from 8a-d and 9a-d undergo acyl mode 5-exo-trig cyclisation to give 3,5-trans pyrrolidinones 11a-d and 14a-d as the major products in low diastereoselectivity (de = 9-36%). The steric nature of the nitrogen substituent attached to the amidyl radical does not have a significant effect on selectivity. The stereochemical outcome is opposite to that expected based upon applying the Beckwith rule. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.05.109

文献信息

• Tethered Aminohydroxylation (TA) Reaction of Amides
  作者：Timothy J. Donohoe、Cedric K. A. Callens、Amber L. Thompson

  DOI：10.1021/ol900631y

  日期：2009.6.4

  The first examples of amide-tethered aminohydroxylation reactions, catalyzed by osmium, showing that the use of N−O-based reoxidants are essential for success, are reported. The system that is described is compatible with a variety of different alkene substitution patterns and ring sizes and works with low loadings in both cyclic and acyclic systems. The levels of diastereoselectivity that were observed

  据报道，催化的酰胺束缚的氨基羟基化反应的第一个例子表明，使用基于N-O的再氧化剂对成功至关重要。所描述的系统与多种不同的烯烃取代方式和环大小兼容，并且在环状和非环状系统中均以低负荷运行。对于在有机合成中使用立体选择性TA反应而言，对于在烯丙基和烯丙基位置上的取代基都观察到的非对映选择性水平很好。
• Synthesis of Chiral Pyrrolidine Derivatives from (S)-Pyroglutamic Acid. I: 7-Substituted (2R,5S)-2-Aryl-1-aza-3-oxabicyclo(3.3.0)octan-8-ones, 7-Substituted (2R,5S)-2-Aryl-1-aza-3-oxabicyclo(3.3.0)oct-6-en-8-ones and 3-Substituted (S)-5-(Hydroxymethyl)-2-pyrrolidinones.
  作者：Tatsuo NAGASAKA、Tomoko IMAI

  DOI：10.1248/cpb.43.1081

  日期：——

  The following chiral pyrrolidine derivatives, 7-substituted (2R, 5S)-2-aryl-1-aza-3-oxabicyclo[3.3.0]octan-8-ones(18-24), 7-substituted (2R, 5S)-2-aryl-1-aza-3-oxabicyclo[3.3.0]oct-6-en-8-ones (25-29) and 3-substituted (S)-5-(hydroxymethyl)-2-pyrrolidinones (30-34), were synthesized starting from (S)-pyroglutamic acid and their absolute configurations were determined based on their 1H-NMR spectra.

  下列手性吡咯烷衍生物，7-取代的(2R, 5S)-2-芳基-1-氮杂-3-氧杂双环[3.3.0]辛-8-酮(18-24)，7-取代的(2R, 5S)-2-芳基-1-氮杂-3-氧杂双环[3.3.0]辛-6-烯-8-酮(25-29)和 3-取代的(S)-5-(羟甲基)-2-吡咯烷酮(30-34)。
• 具有IRAK4抑制剂活性的异喹啉类化合物
  申请人：北京桦冠医药科技有限公司

  公开号：CN112679472A

  公开（公告）日：2021-04-20

  本发明公开了结构如式I的化合物。所述化合物及其互变异构体，以及与适当的酸形成的盐具有抑制IRAK4的活性。同时公开了相应的化合物的制备方法。
• [EN] FUSED BICYCLIC PYRAZOLE DERIVATIVES AND METHODS OF USE THEREOF FOR THE TREATMENT OF HERPESVIRUSES<br/>[FR] DÉRIVÉS BICYCLIQUES FUSIONNÉS DE PYRAZOLE ET LEURS MÉTHODES D'UTILISATION POUR LE TRAITEMENT DE VIRUS HERPÉTIQUES
  申请人：MERCK SHARP & DOHME

  公开号：WO2022132686A1

  公开（公告）日：2022-06-23

  The present invention relates to novel Fused Bicyclic Pyrazole Derivatives of Formula (I): and pharmaceutically acceptable salts thereof, wherein R1, R2, R3, R4, R5, and R6are as defined herein. The present invention also relates to compositions comprising at least one Fused Bicyclic Pyrazole Derivative, and methods of using the Fused Bicyclic Pyrazole Derivatives for treating or preventing a herpesvirus infection in a patient.

  本发明涉及式(I)的新型融合双环吡唑衍生物及其药学上可接受的盐，其中R1、R2、R3、R4、R5和R6如本文所定义。本发明还涉及包含至少一种融合双环吡唑衍生物的组合物，以及使用融合双环吡唑衍生物治疗或预防患者的疱疹病毒感染的方法。
• Hetero-Diels–Alder Addition of Ethyl 2-Nitrosoacrylate to (Z)-Prop-1-enyl Ethers. Stereoselective Synthesis of a Precursor to Sacubitril
  作者：John K. Gallos、Christos I. Stathakis、Stavroula A. Zisopoulou、Thanos Andreou、Theocharis V. Koftis

  DOI：10.1055/a-2029-0015

  日期：——

  A novel, conceptually distinct synthesis of a key precursor to sacubitril, an antihypertensive drug, is presented. The well-demonstrated hetero-Diels–Alder addition of in situ generated nitrosoalkenes to electron-rich enol ethers was engaged to establish the required functionalities with controllable relative stereochemistry. An asymmetric variant of the enol ether enabled access to the target molecule

  介绍了抗高血压药物沙库巴曲的关键前体的一种新颖的、概念上截然不同的合成方法。原位生成的亚硝基烯烃与富电子烯醇醚的杂 Diels-Alder 加成得到了充分证明，用于建立具有可控相对立体化学的所需功能。烯醇醚的不对称变体能够以对映体纯的形式接触目标分子。