N-methyl-N-(1-phenyl-2-propynyl)acetamide | 123772-77-0

• 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-methyl-N-(1-phenyl-2-propynyl)acetamide
• 英文别名: N-methyl-N-(1-phenylprop-2-ynyl)acetamide
• CAS: 123772-77-0
• 化学式: C₁₂H₁₃NO
• 分子量: 187.241
• InChiKey: ANKUIBPNVNCRDW-UHFFFAOYSA-N

物化性质

• 沸点：
  294.1±33.0 °C(Predicted)
• 密度：
  1.056±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  2
• 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：

  四氢吡咯 、 聚合甲醛 、 N-methyl-N-(1-phenyl-2-propynyl)acetamide 在 溶剂黄146 、 copper(l) chloride 作用下， 以 1,4-二氧六环 为溶剂， 反应 8.0h， 以93%的产率得到N-methyl-N-(1-phenyl-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：

  N-(1-phenyl-2-propynyl)acetamide 在 吡啶 、 盐酸 、 sodium tetrahydroborate 、 potassium carbonate 作用下， 以 乙醚 、 乙醇 、 乙腈 为溶剂， 反应 20.83h， 生成 N-methyl-N-(1-phenyl-2-propynyl)acetamide
  参考文献：
  名称：

  Nilsson, Bjoern M.; Hacksell, Uli, Journal of Heterocyclic Chemistry, 1989, vol. 26, p. 269 - 275

  摘要：

  DOI：

文献信息

• Ruthenium-Catalyzed Propargylic Substitution Reactions of Propargylic Alcohols with Oxygen-, Nitrogen-, and Phosphorus-Centered Nucleophiles
  作者：Yoshiaki Nishibayashi、Marilyn Daisy Milton、Youichi Inada、Masato Yoshikawa、Issei Wakiji、Masanobu Hidai、Sakae Uemura

  DOI：10.1002/chem.200400833

  日期：2005.2.18

  The scope and limitations of the ruthenium-catalyzed propargylic substitution reaction of propargylic alcohols with heteroatom-centered nucleophiles are presented. Oxygen-, nitrogen-, and phosphorus-centered nucleophiles such as alcohols, amines, amides, and phosphine oxide are available for this catalytic reaction. Only the thiolate-bridged diruthenium complexes can work as catalysts for this reaction

  提出了钌催化的炔丙醇与以杂原子为中心的亲核试剂进行炔丙基取代反应的范围和局限性。以氧，氮和磷为中心的亲核试剂（例如醇，胺，酰胺和氧化膦）可用于该催化反应。仅硫醇盐桥接的二钌络合物可以用作该反应的催化剂。一些化学计量和催化反应的结果表明，催化炔丙基取代反应是通过原位形成的亚烯基络合物进行的，由此亲核试剂对亚烯基C（γ）原子的攻击是关键步骤。对炔丙醇与几种对位取代苯胺反应的相对速率常数的研究表明，苯胺对亚烯基C（γ）原子的攻击不参与速率的确定步骤，而是苯胺的共轭苯胺的酸度。苯胺攻击C（γ）原子后形成的炔基络合物被认为是决定该催化反应速率的最重要因素。通过使用硫醇盐桥连的二钌配合物来促进该催化反应的关键点被认为是在催化循环中二钌配合物上的亚乙烯基配体与另一种炔丙醇之间的配体交换步骤容易。在该催化反应中，仅硫醇盐桥接的二钌配合物相对于其他单钌配合物更容易促进配体交换步骤的原因应是一个不参与亚烯基形