N-benzyl-N-(2-propynyl)acetamide | 137518-31-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-benzyl-N-(2-propynyl)acetamide
• 英文别名: N-acetyl-N-propargylbenzylamine；N-benzyl-N-prop-2-ynylacetamide
• CAS: 137518-31-1
• 化学式: C₁₂H₁₃NO
• 分子量: 187.241
• InChiKey: XHXZNXPWNXSRBP-UHFFFAOYSA-N

物化性质

• 沸点：
  317.0±35.0 °C(Predicted)
• 密度：
  1.061±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-benzyl-N-(2-propynyl)acetamide 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 以86 %的产率得到N-benzyl-N-(propa-1,2-dien-1-yl)acetamide
  参考文献：
  名称：

  可见光促进简单芳烃的分子内对环加成

  摘要：

  我们通过空间和电子无偏芳基片段的脱芳构化展示了桥接自行车的首次合成。可见光促进方法发生在室温下，具有足够的官能团耐受性。芳基伴侣双官能化的关键是使用萘作为添加剂，通过其扩展的 π 云稳定瞬态（双）自由基。这种效应可能导致它在激进序列中的广泛使用。

  DOI：

  10.1002/anie.202216817
• 作为产物：
  描述：

  N-苄基乙酰胺 、 3-溴丙炔 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 2.0h， 以81%的产率得到N-benzyl-N-(2-propynyl)acetamide
  参考文献：
  名称：

  Palladium catalysed queuing processes. Part 2:

  摘要：

  The palladium catalysed termolecular queuing processes involving aryl iodides, carbon monoxide (1 atm) and in situ generated vinylstannanes as terminating agents afford a variety of complex heterocyclic alpha,beta -unsaturated ketones in good yield. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)01104-2

文献信息

• Tuning the Regioselectivity of Gold-Catalyzed Internal Nitroalkyne Redox: A Cycloisomerization and [3 + 2]-Cycloaddition Cascade for the Construction of <i>spiro</i>-Pseudoindoxyl Skeleton
  作者：Chepuri V. Suneel Kumar、Chepuri V. Ramana

  DOI：10.1021/ol502213w

  日期：2014.9.19

  tricyclic core present in the spiro-pseudoindoxyl natural products has been developed. This involves two intramolecular events: the Au-catalyzed nitroalkyne redox leading to isatogen and its subsequent [3 + 2]-cycloaddition with a suitably positioned olefin. The option to modulate the size of the spiro-annulated ring, which is an important variable in this class of natural products, has been explored. Overall

  已经开发出一种简单的用于在螺-伪吲哚酚天然产物中存在的三环核的构建的多米诺方法。这涉及两个分子内事件：Au催化的硝基炔氧化还原反应会生成致突变物，以及随后发生的[3 + 2]-环加成反应，并带有适当定位的烯烃。来调节大小的选项螺稠环，这是在这个类天然产物的一个重要变量，已探索。总体而言，此过程将线性前体成型为具有完整步骤，原子和氧化还原经济性的三环系统。
• Palladium catalysed tandem cyclisation–anion capture. Part 8: Cascade hydrostannylation—cyclisation–anion capture and cascade hydroboration—cyclisation–anion capture on solid phase
  作者：Ronald Grigg、William S MacLachlan、David T MacPherson、Visuvanathar Sridharan、Selvaratnam Suganthan

  DOI：10.1016/s0040-4020(01)01061-4

  日期：2001.12

  five stereocentres are created, in five component processes (five point diversity), utilising resin bound aryl iodides by hydroboration or hydrostannylation of alkynes, followed by cyclisation–anion capture involving Suzuki or Stille reactions. Three small libraries were prepared to validate the chemistry.

  在五个组分过程（五点多样性）中，通过炔烃的硼氢化或加氢甲锡化利用树脂结合的芳基碘化物，然后进行涉及Suzuki或Stille反应的环化-阴离子捕获，可创建多达四个键和五个立体中心。准备了三个小型文库以验证化学性质。
• Phenyl-substituted analogs of oxotremorine as muscarinic antagonists
  作者：Bjoern M. Nilsson、Hugo M. Vargas、Bjoern Ringdahl、Uli Hacksell

  DOI：10.1021/jm00080a013

  日期：1992.1

  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.
• Palladium catalysed queuing processes. Part 2:
  作者：Usman Anwar、Adele Casaschi、Ronald Grigg、José M Sansano

  DOI：10.1016/s0040-4020(00)01104-2

  日期：2001.2

  The palladium catalysed termolecular queuing processes involving aryl iodides, carbon monoxide (1 atm) and in situ generated vinylstannanes as terminating agents afford a variety of complex heterocyclic alpha,beta -unsaturated ketones in good yield. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Visible‐Light Promoted Intramolecular <i>para</i> ‐Cycloadditions on Simple Aromatics
  作者：Maurizio Chiminelli、Andrea Serafino、Davide Ruggeri、Luciano Marchiò、Franca Bigi、Raimondo Maggi、Max Malacria、Giovanni Maestri

  DOI：10.1002/anie.202216817

  日期：2023.3.13

  We present the first synthesis of bridged bicycles through the dearomatization of sterically and electronically unbiased aryl fragments. The visible-light promoted method occurs at room temperature and has ample functional-group tolerance. The key to the difunctionalization of the aryl partner is the use of naphthalene as an additive, which stabilizes transient (bi)radicals through its extended π cloud

  我们通过空间和电子无偏芳基片段的脱芳构化展示了桥接自行车的首次合成。可见光促进方法发生在室温下，具有足够的官能团耐受性。芳基伴侣双官能化的关键是使用萘作为添加剂，通过其扩展的 π 云稳定瞬态（双）自由基。这种效应可能导致它在激进序列中的广泛使用。