N-benzyl-N-methyl-3-oxobutanamide | 71392-09-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N-benzyl-N-methyl-3-oxobutanamide
• 英文别名: N-Benzyl-N-Methylacetoacetamide
• CAS: 71392-09-1
• 化学式: C₁₂H₁₅NO₂
• 分子量: 205.257
• InChiKey: KVCNVQYZBQIYTF-UHFFFAOYSA-N

物化性质

• 沸点：
  348.5±35.0 °C(Predicted)
• 密度：
  1.081±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-benzyl-N-methyl-3-oxobutanamide 生成 Acetoacet-N-methyl-N-benzylamid-2,3-dioxim
  参考文献：
  名称：

  2,3-Dioximes of Various Substituted Acetoacetamides and Their Metal Chelates

  摘要：

  提供了制备各种取代乙酰乙酰胺二肟的方法。通过电位滴定pH测量确定了这些化合物的解离常数和它们的金属螯合物的稳定常数。讨论了酰胺基团取代基对稳定性变化的影响。

  DOI：

  10.1139/v74-101
• 作为产物：
  描述：

  N-(苯基甲基)-氨基甲酸甲酯 在 lithium aluminium tetrahydride 作用下， 生成 N-benzyl-N-methyl-3-oxobutanamide
  参考文献：
  名称：

  Intramolecular Addition of Stabilized Enolates to (η⁶-Arene)ruthenium Complexes:  Synthesis of Ru-Coordinated Azaspirocycles

  摘要：

  [GRAPHICS]Stabilized enolates attached to, cationic (arene)(RuCp)-Cp-II complexes via an amide linkage were found to participate in nucleophilic aromatic addition reactions resulting in the formation of novel cyclohexadienyl-Ru azaspirocycles. Enolate addition to the activated arene ring was found to proceed with complete stereoselectivity.

  DOI：

  10.1021/ol991123v

文献信息

• α-Diazoacetamides in Sc(OTf)3-Catalyzed Tiffeneau–Demjanov Ring Expansion: Application towards the Synthesis of Rare Bicyclic Pyrazoles
  作者：Mikhail Krasavin、Sergey Chuprun、Dmitry Dar’in、Grigory Kantin、Petr Zhmurov

  DOI：10.1055/s-0039-1690047

  日期：2020.3

  A novel Sc(OTf)3-catalyzed Tiffeneau–Demjanov ring expansion of six-membered cyclic ketones has been developed. The resulting seven-membered cyclic β-keto carboxamides were found to be versatile precursors to rare bicyclic pyrazoles obtained in modest to good yields via condensation with aryl hydrazines in the presence of Lawesson’s reagent.

  已经开发了一种新型的 Sc(OTf)3 催化的六元环酮的 Tiffeneau-Demjanov 环扩展。发现所得的七元环状 β-酮甲酰胺是稀有双环吡唑的通用前体，通过在劳森试剂的存在下与芳基肼缩合以中等至良好的产率获得。
• NEW ANALOGS AS ANDROGEN RECEPTOR AND GLUCOCORTICOID RECEPTOR MODULATORS
  申请人：Oncostellae, S.L.

  公开号：EP3480201A1

  公开（公告）日：2019-05-08

  The present invention relates to novel dihydropyridine derivatives of formula (I): as modulators of nuclear receptors selected from androgen receptor and glucocorticoid receptor, to processes for their preparation, to pharmaceutical compositions comprising said compounds and to the use of said for manufacturing a medicament for the treatment of pathological conditions or diseases that can improve by modulation of androgen receptor and/or glucocorticoid receptor, selected from cancer, metastasizing cancers, benign prostate hyperplasia, polycystic ovary syndrome (PCOS), hair loss, hirsutism, acne, hypogonadism, muscle wasting diseases, cachexia, Cushing's syndrome, anti-psychotic drug induced weight gain, obesity, post-traumatic stress disorder and alcoholism.

  本发明涉及一种新型的二氢吡啶衍生物，其化学式为(I)：作为选择的核受体调节剂，所述核受体包括雄激素受体和糖皮质激素受体，以及其制备方法，包括所述化合物的制药组合物和利用所述化合物制造用于治疗可以通过调节雄激素受体和/或糖皮质激素受体改善的病理情况或疾病的药物，所述病理情况或疾病包括癌症、转移性癌症、良性前列腺增生、多囊卵巢综合征（PCOS）、脱发、多毛症、痤疮、性腺功能减退、肌肉消耗性疾病、虚弱、库欣综合征、抗精神病药物诱导的体重增加、肥胖、创伤后应激障碍和酗酒。
• Synthesis of the 1,3,4-Oxadiazole Core through Thermolysis of Geminal Diazides
  作者：Hellmuth Erhardt、Fabian Mohr、Stefan F. Kirsch

  DOI：10.1002/ejoc.201601119

  日期：2016.12

  The thermolysis of geminal diazides derived from acylacetate compounds is an efficient tool for the rapid construction of the 1,3,4-oxadiazole core. While a broad range of ethyl esters undergoes smooth transformation to the desired heterocycles that contain the ester moiety in moderate to high yields, the analogous tert-butyl esters give rise to the oxadiazoles with acyl groups, presumably through

  来自酰基乙酸酯化合物的孪生二叠氮化物的热解是快速构建 1,3,4-恶二唑核的有效工具。虽然范围广泛的乙酯以中等至高产率顺利转化为含有酯部分的所需杂环，但类似的叔丁酯产生具有酰基的恶二唑，可能是通过脱羧途径，然后是新的酰基转移。
• Organometallic induced self-condensation of carboxamides
  作者：F. Babudri、F. Ciminale、L. Di Nunno、S. Florio

  DOI：10.1016/0040-4020(82)80100-2

  日期：1982.1

  N,N-Disubstituted carboxamides containing α-hydrogen atoms undergo self-condensation reaction simply on treatment with Grignard reagents or n-BuLi in THF room temp. The reaction is considerably influenced steric hindrance at the α-carbon and the condensing agent utilized. A possble Claisen-type mechanism is also reported.

  含有α-氢原子的N，N-二取代羧酰胺仅在THF室温下用格氏试剂或正丁基锂处理即可进行自缩合反应。该反应在α-碳和所用的缩合剂上对位阻有很大影响。还报道了一种可能的克莱森型机制。
• Ruthenium-Coordinated Spirolactams via Intramolecular Nucleophilic Addition to η⁶-Arene Metal Complexes
  作者：F. Christopher Pigge、John J. Coniglio、Shiyue Fang

  DOI：10.1021/om020592p

  日期：2002.10.1

  contrast, related arene ruthenium complexes prepared from benzyl acetoacetate and phenethyl acetoacetamide failed to undergo spirocyclization, but were found to participate in intramolecular SNAr reactions (leading to formation of tetralone and benzazepinone ring systems, respectively). Thus, the conformational mobility of the side chain linking the nucleophilic center to the coordinated arene ring

  （η环己二烯基钌（II）结合有azaspirocyclic环系络合物已经从制备6 - ñ -苄基乙酰乙酰胺）CPRU（II）前体通过分子内亲核芳族加成/烯醇化物捕获反应序列。发现螺环化方法适用于各种烷基，烷氧基和氯取代的N-苄基乙酰乙酰胺配体，环己二烯基产物的分离产率为44％至86％。相反，相关芳烃钌络合物制备了乙酰苯和苯乙基的乙酰乙酰胺未能接受螺环，但被发现参与分子小号ñAr反应（分别导致四氢萘酮和苯并ze庚酮环系统的形成）。因此，在这些反应中，将亲核中心与配位的芳烃环连接的侧链的构象迁移性对于控制芳族化合物的区域选择性很重要。LiAlH 4将几种螺内酰胺复合物还原为相应的Ru配位螺环胺；但是，通过配体质子化从CpRu（II）中心除去环己二烯基部分的尝试失败。