1,5-二甲基-2-吡咯烷酮 | 5075-92-3

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: 1,5-二甲基-2-吡咯烷酮
• 英文名称: 1,5-dimethylpyrrolidin-2-one
• 英文别名: 1,5-dimethyl-2-pyrrolidone；1,5-Dimethyl-2-pyrrolidinone
• CAS: 5075-92-3
• 化学式: C₆H₁₁NO
• mdl: MFCD00003194
• 分子量: 113.159
• InChiKey: FILVIKOEJGORQS-UHFFFAOYSA-N

物化性质

• 沸点：
  215-217 °C/743 mmHg (lit.)
• 密度：
  0.982 g/mL at 25 °C (lit.)
• 闪点：
  193 °F
• 稳定性/保质期：
  如果按照规格使用和储存，则不会分解，未有已知危险发生。

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.833
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• WGK Germany：
  3
• 危险品标志：
  Xi
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2933790090
• 储存条件：
  请将药品存放在密闭、阴凉干燥的地方。

制备方法与用途

化学性质
这是一种无色液体，沸点在99.06 kPa时为215-217℃，而在1.73 kPa时为85℃，相对密度为0.982，折光率为1.4650。它能溶于乙醇和丙酮，但不溶于水。

用途
主要用作有机合成的中间体。

生产方法
在反应釜中加入194克戊-4-酮酸、500毫升35%甲胺及10克骨架镍，密闭后通入氢气至7-14 MPa。搅拌并加热至140℃，保持5小时。反应结束后冷却，取出反应物并过滤掉催化剂。所得滤液进行蒸馏，在84-86℃（1.73 kPa）的条件下收集馏分，最终得到1,5-二甲基-2-吡咯烷酮，收率为74-77%。

反应信息

• 作为反应物：
  描述：

  1,5-二甲基-2-吡咯烷酮 在 (Cl₃CO)2CO 作用下， 以 甲苯 为溶剂， 反应 6.0h， 生成 5-chloro-1,2-dimethyl-3,4-dihydro-2H-pyrrol-1-ium;chloride
  参考文献：
  名称：

  Dannhardt; Bauer, Pharmazie, 1996, vol. 51, # 11, p. 805 - 810

  摘要：

  DOI：
• 作为产物：
  描述：

  当归内酯 在 1% Pd on activated carbon 、 氢气 作用下， 以 水 、 甲苯 为溶剂， 20.0~50.0 ℃ 、2.03 MPa 条件下， 反应 3.0h， 生成 1,5-二甲基-2-吡咯烷酮
  参考文献：
  名称：

  在γ-羟基γ-内酰胺中钯催化的CO氢解作为5-烷基（芳基）吡咯烷-2-酮的有效方法

  摘要：

  摘要 通过 Pd/Sibunit 催化 5-R-5-羟基吡咯烷-2-酮与分子氢的 C-O 氢解合成了 5-R-Pyrrolidin-2-one。

  DOI：

  10.1007/s11172-015-0945-z
• 作为试剂：
  描述：

  N,N-二甲基甲酰胺-d7 、 在 1,5-二甲基-2-吡咯烷酮 、 caesium carbonate 、 cesium fluoride 、 potassium iodide 作用下， 反应 13.0h， 以13%的产率得到
  参考文献：
  名称：

  Calix[4]arene-Based (Hemi)carcerands and Carceplexes: Synthesis, Functionalization, and Molecular Modeling Study

  摘要：

  AbstractThe synthesis of 11 calix[4]arene‐based carceplexes obtained by solvent or doped inclusion is reported. Carceplexes with amides, for example, DMF, NMP, and 1,5‐dimethyl‐2‐pyrrolidinone, and sulfoxides, for example, DMSO and thiolane‐1‐oxide, were obtained by solvent inclusion. In these cases the yield of the carceplex decreases with increasing guest size. Potential guests that do not form carceplexes by solvent inclusion, such as 2‐butanone and 3‐sulfolene, could be incarcerated by doped inclusion with 1,5‐dimethyl‐2‐pyrrolidinone as a solvent “doped” with 5–15 vol% of potential guest. The amide bridges of the carceplexes were converted into thioamide bridges in essentially quantitative yield by means of Lawesson's reagent in refluxing xylene. The dynamic properties of the incarcerated guests were examined by 2D NMR spectroscopy. Whereas for most guests a preference for one orientation inside the calix[4]arene‐based (thia)carcerands was observed, for DMA, NMP, and ethyl methyl sulfoxide inside calix[4]arene‐based (thia)carcerandstwo different orientationswere present. The energy barriers for interconversion between the various orientations of DMA, NMP, and ethyl methyl sulfoxide inside calix[4]arene‐based (thia)‐carcerands were determined with 2D EXSY NMR. The energy barriers are higher for the thiacarcerands than for the corresponding carcerands with amide bridges. This may be due to the stronger hydrogen‐bond‐donating character of the thioamide group. Furthermore, molecular modeling simulations indicate that in case of the thiacarcerand the cavity is smaller as a result of a smaller diametrical distance between the NHatoms. Our results demonstrate that molecular modeling can be used to estimate the energy barriers for interconversion; the calculated activation energies showed good quantitative agreement with the experimental values.

  DOI：

  10.1002/chem.19970030421

文献信息

• A Facile Direct Route to <i>N</i> ‐(Un)substituted Lactams by Cycloamination of Oxocarboxylic Acids without External Hydrogen
  作者：Hu Li、Hongguo Wu、Heng Zhang、Yaqiong Su、Song Yang、Emiel J. M. Hensen

  DOI：10.1002/cssc.201901780

  日期：2019.8.22

  Lactams are privileged in bioactive natural products and pharmaceutical agents and widely featured in functional materials. This study presents a novel versatile approach to the direct synthesis of lactams from oxocarboxylic acids without catalyst or external hydrogen. The method involves the in situ release of formic acid from formamides induced by water to facilitate efficient cycloamination. Water

  内酰胺在生物活性天然产物和药物制剂中享有特权，并在功能材料中得到广泛应用。这项研究提出了一种新颖的通用方法，无需催化剂或外部氢就可从含氧羧酸直接合成内酰胺。该方法涉及从水诱导的甲酰胺中原位释放甲酸，以促进有效的环胺化。水还抑制副产物的形成。通过模型实验和密度泛函理论计算的结合阐明了这种非常规途径，其中发现环状亚胺（5-甲基-3,4-二氢-2-吡咯烷酮及其互变异构结构）是形成内酰胺的有利中间体。与包括级联还原胺化和环化的常规方法形成对比。N-未取代和N-取代的内酰胺。
• [EN] BORON-CONTAINING RHO KINASE INHIBITORS<br/>[FR] INHIBITEURS DE LA RHO KINASE CONTENANT DU BORE
  申请人：PERCIPIAD INC

  公开号：WO2021011873A1

  公开（公告）日：2021-01-21

  The present invention provides boron-containing isoquinoline compounds as protein kinase-modulating compounds. These compounds are useful as neuroprotective and neuro-regenerative agents for the amelioration of glaucoma and other ocular neuropathies.

  本发明提供了含硼的异喹啉化合物作为蛋白激酶调节化合物。这些化合物可用作神经保护和神经再生剂，用于改善青光眼和其他眼神经病变。
• THERAPEUTICALLY ACTIVE COMPOUNDS AND THEIR METHODS OF USE
  申请人：Lemieux Rene M.

  公开号：US20150031627A1

  公开（公告）日：2015-01-29

  Provided are methods of treating a cancer characterized by the presence of a mutant allele of IDH1/2 comprising administering to a subject in need thereof a compound described here.

  提供的方法是治疗一种由IDH1/2突变等位基因特征性存在的癌症，包括向需要此治疗的患者施用此处描述的化合物。
• LACTAM COMPOUNDS AS EP4 RECEPTOR-SELECTIVE AGONISTS FOR USE IN THE TREATMENT OF EP4-MEDIATED DISEASES AND CONDITIONS
  申请人：CAYMAN CHEMICAL COMPANY, INC.

  公开号：US20160060216A1

  公开（公告）日：2016-03-03

  Disclosed herein are compounds of formula (I) wherein L 1 , L 2 , L 3 , L 4 , R 1 , R 4 , R 5 , R 6 , and s are as defined in the specification. Compounds of formula (I) are EP 4 agonists useful in the treatment of glaucoma, osteoporosis, bone fracture, periodontal bone loss, orthopedic implant, alopecia, neuropathic pain, and related disorders. Pharmaceutical compositions and methods of treating conditions or disorders are also described.

  披露了公式(I)的化合物 其中L 1 , L 2 , L 3 , L 4 , R 1 , R 4 , R 5 , R 6 ，和s如说明书所定义。 公式(I)的化合物是EP 4 激动剂，用于治疗青光眼、骨质疏松症、骨折、牙周骨丢失、矫形植入物、脱发、神经性疼痛和相关的疾病。 还描述了药物组合物和治疗条件或疾病的方法。
• THIAZOLIDINONE COMPOUNDS AND USE THEREOF
  申请人：National Health Research Institutes

  公开号：US20170253569A1

  公开（公告）日：2017-09-07

  A pharmaceutical composition containing a compound of Formula (I) for treating an opioid receptor-associated condition. Also disclosed is a method for treating an opioid receptor-associated condition using such a compound. Further disclosed are two sets of thiazolidinone compounds of formula (I): (i) compounds each having an enantiomeric excess greater than 90% and (ii) compounds each being substituted with deuterium.

  一种含有化合物（I）的药物组合物，用于治疗与阿片受体相关的疾病。还公开了一种使用这种化合物治疗阿片受体相关疾病的方法。进一步公开了两组式（I）的噻唑烷酮化合物：（i）每种化合物的对映体过量大于90%；（ii）每种化合物被氘取代。

表征谱图