N-(2-丙炔基)乙酰胺 | 65881-41-6

• 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: N-(2-丙炔基)乙酰胺
• 中文别名: N-炔丙基乙酰胺
• 英文名称: N-Acetylpropargylamine
• 英文别名: N-(prop-2-yn-1-yl)acetamide；Acetamide, N-2-propynyl-；N-prop-2-ynylacetamide
• CAS: 65881-41-6
• 化学式: C₅H₇NO
• mdl: MFCD14631295
• 分子量: 97.1167
• InChiKey: GGOQYHOZFCWTNM-UHFFFAOYSA-N

物化性质

• 熔点：
  83-85 °C
• 沸点：
  245.6±23.0 °C(Predicted)
• 密度：
  0.963±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2924199090
• 储存条件：
  2~8℃

反应信息

• 作为反应物：
  描述：

  N-(2-丙炔基)乙酰胺 在 sodium hydride 、 溶剂黄146 、 copper(l) chloride 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 12.5h， 生成 N-benzyl-N-(4-pyrrolidin-1-ylbut-2-ynyl)acetamide
  参考文献：
  名称：

  Phenyl-substituted analogs of oxotremorine as muscarinic antagonists

  摘要：

  A series of phenyl-substituted analogues of the muscarinic agent oxotremorine (1) have been prepared. The new compounds (3b-11b and 9c) were assayed for antimuscarinic activity on the isolated guinea pig ileum and in intact mice. They were also evaluated for ability to inhibit the binding of the muscarinic antagonist (-)-[H-3]-N-methylscopolamine to homogenates of the rat cerebral cortex. The phenyl-substituted derivatives were devoid of intrinsic muscarinic activity. Instead, they behaved as competitive muscarinic antagonists in these assays with similar or lower affinity for muscarinic receptors than the corresponding methyl-substituted analogues. The succinimide (8b) and the pyrrolidone (3b) derivatives of 1 substituted with a phenyl group at position 1 of the butynyl chain showed the highest antimuscarinic potency with dissociation constants (K(D)) of 0.10 and 0.20-mu-M, respectively, in the ileum assay. The phenyl-substituted analogues showed an approximately 10-fold lower in vivo antimuscarinic potency than their corresponding methyl-substituted positional isomers. A correlation was observed between in vitro and in vivo potency within subsets consisting of methyl- and phenyl-substituted derivatives.

  DOI：

  10.1021/jm00080a013
• 作为产物：
  描述：

  炔丙胺 在 吡啶 、 乙酸酐 作用下， 以 二氯甲烷 为溶剂， 生成 N-(2-丙炔基)乙酰胺
  参考文献：
  名称：

  EP1300464

  摘要：

  公开号：

文献信息

• Cu(I)-Catalyzed Synthesis of Dihydropyrimidin-4-ones toward the Preparation of β- and β³-Amino Acid Analogues
  作者：Basker Rajagopal、Ying-Yu Chen、Chun-Chi Chen、Xuan-Yu Liu、Huei-Ren Wang、Po-Chiao Lin

  DOI：10.1021/jo402670d

  日期：2014.2.7

  A copper(I)-catalyzed synthesis of substituted dihydropyrimidin-4-ones from propargyl amides via the formation of ketenimine intermediate has been successfully developed; the synthesis afforded good isolated yields (80–95%). The mild reaction conditions at room temperature allow the reaction to proceed to completion in a few hours without altering the stereochemistry. Further, by involving a variety

  已经成功地开发了铜（I）催化炔酮胺中间体从炔丙基酰胺合成取代的二氢嘧啶-4-酮。合成得到良好的分离产率（80-95％）。室温下温和的反应条件可使反应在数小时内完成，而无需改变立体化学。另外，通过涉及多种反应性亲核试剂，将得到的被取代的二氢嘧啶-4-酮被优雅转化成相应的β-和β 3 -氨基酸的类似物。
• [EN] FUSED PENTACYCLIC ANTI - PROLIFERATIVE COMPOUNDS<br/>[FR] COMPOSÉS PENTACYCLIQUES FUSIONNÉS ANTI-PROLIFÉRATIFS
  申请人：PHARMINOX LTD

  公开号：WO2012175991A1

  公开（公告）日：2012-12-27

  The present invention relates to novel compounds of formula (I) wherein X, Q, R1, R2, R3, R4, R5, R6, R7, R8, R21, R22 and R23 are as defined herein. The compounds of formula (I) are inhibitors of telomerase enzyme function and are accordingly useful for the treatment cellular proliferation disorders, such as cancer.

  本发明涉及式(I)的新化合物，其中X、Q、R1、R2、R3、R4、R5、R6、R7、R8、R21、R22和R23如本文所定义。式(I)的化合物是端粒酶酶功能的抑制剂，因此对于治疗细胞增殖紊乱，如癌症，是有用的。
• [EN] INHIBITORS OF HEPATITIS C VIRUS REPLICATION<br/>[FR] INHIBITEURS DE LA RÉPLICATION DU VIRUS DE L'HÉPATITE C
  申请人：MERCK SHARP & DOHME

  公开号：WO2010111483A1

  公开（公告）日：2010-09-30

  The present invention relates to compounds of formula (I) that are useful as hepatitis C virus (HCV) NS5A inhibitors, the synthesis of such compounds, and the use of such compounds for inhibiting HCV NS5A activity, for treating or preventing HCV infections and for inhibiting HCV viral replication and/or viral production in a cell-based system.

  本发明涉及一种公式（I）的化合物，该化合物可用作丙型肝炎病毒（HCV）NS5A抑制剂，以及该类化合物的合成，以及利用该类化合物抑制HCV NS5A活性，用于治疗或预防HCV感染，以及在基于细胞的系统中抑制HCV病毒复制和/或病毒产生。
• Water-Soluble Gold-N-Heterocyclic Carbene Complexes for the Catalytic Homogeneous Acid- and Silver-Free Hydration of Hydrophilic Alkynes
  作者：Houssein Ibrahim、Pierre de Frémont、Pierre Braunstein、Vincent Théry、Lionel Nauton、Federico Cisnetti、Arnaud Gautier

  DOI：10.1002/adsc.201500729

  日期：2015.12.14

  Water-soluble gold(III/I) N-heterocylic carbene complexes behave as efficient catalysts for the hydration of terminal alkynes in neat water. The transformation proceeds in the absence of Brønsted acids or halide scavengers and is suitable for sensitive substrates. Kinetic profiles and DFT studies provide a clear picture of intermediates present during catalysis.

  水溶性金（III / I）N-杂环卡宾配合物可作为纯净水中末端炔烃水合的有效催化剂。在不存在布朗斯台德酸或卤化物清除剂的情况下进行转化，适用于敏感底物。动力学曲线和DFT研究提供了催化过程中存在的中间体的清晰图片。
• Structure activity relationship of 3-nitro-2-(trifluoromethyl)-2H-chromene derivatives as P2Y6 receptor antagonists
  作者：Young-Hwan Jung、Shanu Jain、Varun Gopinatth、Ngan B. Phung、Zhan-Guo Gao、Kenneth A. Jacobson

  DOI：10.1016/j.bmcl.2021.128008

  日期：2021.6

  Various 6-alkynyl analogues of a known 3-nitro-2-(trifluoromethyl)-2H-chromene antagonist 3 of the Gq-coupled P2Y6 receptor (P2Y6R) were synthesized using a Sonogashira reaction to replace a 6-iodo group. The analogues were tested in a functional assay consisting of inhibition of calcium mobilization in P2Y6R-expressing astrocytoma cells elicited by native P2Y6R agonist UDP. 6-Ethynyl and 6-cyano groups

  使用 Sonogashira 反应合成了 G q偶联 P2Y 6受体 (P2Y 6 R) 的已知 3-硝基-2-(三氟甲基)-2 H-色烯拮抗剂3的各种 6-炔基类似物，以取代 6-碘团体。这些类似物在功能测定中进行了测试，该测定包括抑制由天然 P2Y 6 R 激动剂 UDP 引起的表达 P2Y 6 R 的星形细胞瘤细胞中的钙动员。安装了 6-乙炔基和 6-氰基，并且炔烃通过烷基和芳基间隔基延伸。最有效的拮抗剂，IC 50约为 1 µM，被发现为三烷基甲硅烷基乙炔基7和8 （亲和力比参考3高 3-5 倍）、丙-2-炔-1-基氨基甲酸叔丁酯14和p -羧基苯基-乙炔基16衍生物、 3和8表现出对UDP诱导的磷酸肌醇产生的可克服的拮抗作用。其他扩链末端羧酸酯衍生物的效力不如相应的甲酯衍生物。因此，该色烯系列中的 6 位适合具有取代灵活性的衍生化，即使是空间延伸的链，也不会损失 P2Y 6 R