3-乙酰基-1-甲基-2-吡咯烷酮 | 60044-08-8

• 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: 3-乙酰基-1-甲基-2-吡咯烷酮
• 英文名称: 3-acetyl-1-methylpyrrolidin-2-one
• CAS: 60044-08-8
• 化学式: C₇H₁₁NO₂
• mdl: MFCD02683822
• 分子量: 141.17
• InChiKey: FNRBNSZXDRIQCZ-UHFFFAOYSA-N

物化性质

• 沸点：
  277.3±33.0 °C(Predicted)
• 密度：
  1.107±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.714
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933790090
• 危险性防范说明：
  P264,P280,P302+P352,P305+P351+P338,P332+P313,P337+P313,P362
• 危险性描述：
  H315,H319

反应信息

• 作为反应物：
  描述：

  3-乙酰基-1-甲基-2-吡咯烷酮 在 hydrazine hydrate 、 溴 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 氯仿 、 水 、 二甲基亚砜 、 异丙醇 为溶剂， 反应 36.5h， 生成 3-(3-(2-(((4-chloro-1-(tetrahydro-2H-pyran-2-yl)-3H-benzo[d]imidazol-5-yl)methyl)(methyl)amino)pyrimidin-4-ylamino)-1H-pyrazol-5-yl)-1-methylpyrrolidin-2-one
  参考文献：
  名称：

  Leveraging the Pre-DFG Residue Thr-406 To Obtain High Kinase Selectivity in an Aminopyrazole-Type PAK1 Inhibitor Series

  摘要：

  To increase kinase selectivity in an aminopyrazole-based PAK1 inhibitor series, analogues were designed to interact with the PAKI deep-front pocket pre-DFG residue Thr-406, a residue that is hydrophobic in most kinases. This goal was achieved by installing lactam head groups to the aminopyrazole hinge binding moiety. The corresponding analogues represent the most kinase selective ATP-competitive Group I PAK inhibitors described to date. Hydrogen bonding with the Thr-406 side chain was demonstrated by X-ray crystallography, and inhibitory activities, particularly against kinases with hydrophobic pre-DFG residues, were mitigated. Leveraging hydrogen bonding side chain interactions with polar pre-DFG residues is unprecedented, and similar strategies should be applicable to other appropriate kinases.

  DOI：

  10.1021/acsmedchemlett.5b00151
• 作为产物：
  描述：

  N-甲基吡咯烷酮 、 乙酸乙酯 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.67h， 以27%的产率得到3-乙酰基-1-甲基-2-吡咯烷酮
  参考文献：
  名称：

  通过[3 + 2]和[3 + 3]氮杂环化反应轻松合成螺环内酰胺

  摘要：

  通过适当的烯胺与马来酸酐或衣康酸酐之间的氮杂环化反应，以非对映选择性的方式组装5,5-和5,6-螺环内酰胺。可用的起始原料以及简单的步骤可以考虑将合成的螺环化合物作为筛选库合成的视角构建基块。

  DOI：

  10.1002/ejoc.202100255

文献信息

• Fe(III) Complex Compounds For The Treatment And Prophylaxis Of Iron Deficiency Symptoms And Iron Deficiency Anemias
  申请人：Bark Thomas

  公开号：US20130109662A1

  公开（公告）日：2013-05-02

  The invention relates to iron(III) complex compounds and pharmaceutical compositions comprising them for the use as medicaments, in particular for the treatment and/or prophylaxis of iron deficiency symptoms and iron deficiency anemias.

  这项发明涉及铁（III）配合物和包括它们的药物组合物，用作药物，特别是用于治疗和/或预防缺铁症状和缺铁性贫血。
• Aerobic α-hydroxylation of β-keto esters and amides by co-catalysis of SmI3 and I2 under mild base-free conditions
  作者：Shun-Ming Yu、Kai Cui、Fei Lv、Zhen-Yu Yang、Zhu-Jun Yao

  DOI：10.1016/j.tetlet.2016.05.052

  日期：2016.6

  A clean base-free α-hydroxylation of β-keto esters and amides has been developed, in which air was used as the oxygen source and SmI3 and I2 were applied as the catalysts, affording the corresponding α-hydroxylated 1,3-dicarbonyl products in good to excellent yields under mild conditions. Mechanism discussion shows that both oxygen atoms of dioxygen are utilized and incorporated into the product through

  已经开发出清洁的无碱的β-酮酯和酰胺的α-羟基化反应，其中空气用作氧气源，SmI 3和I 2被用作催化剂，得到相应的α-羟基化的1,3-在温和条件下，二羰基产品的收率好至极好。机理讨论表明，双氧的两个氧原子都被利用，并通过独特的自由基过程掺入产物中。
• o-Iodoxybenzoic Acid (IBX)–Iodine Mediated One-Pot Deacylative Sulfonylation of 1,3-Dicarbonyl Compounds: A Synthesis of β-Carbonyl Sulfones
  作者：Chutima Kuhakarn、Praewpan Katrun、Teerawat Songsichan、Darunee Soorukram、Manat Pohmakotr、Vichai Reutrakul

  DOI：10.1055/s-0036-1588900

  日期：——

  combination of o-iodoxybenzoic acid (IBX) and a catalytic amount of iodine is found to promote a facile one-pot deacylative sulfonylation reaction of 1,3-dicarbonyl compounds with sodium sulfinates to yield β-carbonyl sulfones. The present method provides the target products bearing a wide variety of functional groups in one step and in good yields. A combination of o-iodoxybenzoic acid (IBX) and a catalytic

  摘要 发现邻碘氧苯甲酸（IBX）和催化量的碘的组合可促进1,3-二羰基化合物与亚磺酸钠的简便的一锅脱酰基磺酰化反应，生成β-羰基砜。本发明的方法一步一步提供高产率的带有多种官能团的目标产物。 发现邻碘氧苯甲酸（IBX）和催化量的碘的组合可促进1,3-二羰基化合物与亚磺酸钠的简便的一锅脱酰基磺酰化反应，生成β-羰基砜。本发明的方法一步一步提供高产率的带有多种官能团的目标产物。
• Chiral Primary Amine Catalyzed Asymmetric α-Benzylation with In Situ Generated<i>ortho</i>-Quinone Methides
  作者：Yunbo Zhu、Wen-Zhao Zhang、Long Zhang、Sanzhong Luo

  DOI：10.1002/chem.201605302

  日期：2017.1.26

  A dual activation strategy integrating primary amine catalysis and Lewis base activation has been developed for an asymmetric α‐benzylation reaction. Enamines derived from β‐ketocarbonyls could react effectively with in situ generated ortho‐quinone methides under Lewis base activation in asymmetric α‐benzylation of β‐ketocarbonyls and α‐branched aldehydes. The approach enables the creation of acyclic

  已开发出一种结合伯胺催化和路易斯碱活化的双重活化策略，用于不对称的α-苄基化反应。β-酮羰基衍生的烯胺可以在Lewis碱活化下与原位生成的邻醌甲基化物有效反应，从而使β-酮羰基和α-支化醛发生不对称的α-苄基化反应。该方法可以创建具有出色对映选择性和良好活性的无环全碳四元立体中心。
• 2-Aminobenzimidazole Organocatalyzed Asymmetric Amination of Cyclic 1,3-Dicarbonyl Compounds
  作者：Alejandro Baeza、Paz Trillo、Melania Gómez-Martínez、Diego Alonso

  DOI：10.1055/s-0034-1379494

  日期：——

  The use of a trans-cyclohexanediamine benzimidazole derivative as a hydrogen-bond catalyst for the electrophilic amination of cyclic 1,3-dicarbonyl compounds is herein presented. High yields and enantioselectivities varying from moderate to excellent are generally obtained using mild reaction conditions and as low as 1 mol% of catalyst loading.

  本文介绍了反式环己二胺苯并咪唑衍生物作为氢键催化剂用于环状 1,3-二羰基化合物的亲电胺化的用途。通常使用温和的反应条件和低至 1 mol% 的催化剂负载量可以获得高产率和从中等到优异的对映选择性。