N-[(1S)-1-(4-fluorophenyl)prop-2-ynyl]acetamide | 226699-10-1

• 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-[(1S)-1-(4-fluorophenyl)prop-2-ynyl]acetamide
• CAS: 226699-10-1
• 化学式: C₁₁H₁₀FNO
• 分子量: 191.205
• InChiKey: MXBKTPKPEFQAQJ-NSHDSACASA-N

物化性质

• 沸点：
  340.3±37.0 °C(Predicted)
• 密度：
  1.148±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：
  0.18
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-[(1S)-1-(4-fluorophenyl)prop-2-ynyl]acetamide 、 乙烯 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 甲苯 为溶剂， 生成 N-[(1S)-1-(4-fluorophenyl)-2-methylidenebut-3-enyl]acetamide
  参考文献：
  名称：

  Microwave-assisted ethylene–alkyne cross-metathesis: synthesis of chiral 2-(N-1-acetyl-1-arylmethyl)-1,3-butadienes

  摘要：

  Chiral 1-arylpropargyl amides, which are resistant to undergoing ethylene-alkyne cross-metathesis at atmospheric pressure, were reacted under microwave irradiation to afford enantiomerically enriched 2-(N-1-acetyl-1-arylmethyl)-1,3-butadienes within a few minutes. Enantiomerically enriched amides underwent ethylene-alkyne cross-metathesis with retention of configuration at the propargylic/allylic position. A series of chiral 2-(N-1-acetyl-1-arylmethyl)-1,3-butadienes were synthesised with ee >= 95%; these latter compounds could be used as building blocks for the synthesis of new antifungal and antiaromatase agents. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.08.002
• 作为产物：
  描述：

  (+/-)-N-[1-(4-fluorophenyl)-2-propynyl]acetamide 在 盐酸 、 Candida antarctica lipase 、 三乙胺 作用下， 生成 N-[(1S)-1-(4-fluorophenyl)prop-2-ynyl]acetamide
  参考文献：
  名称：

  Microwave-assisted ethylene–alkyne cross-metathesis: synthesis of chiral 2-(N-1-acetyl-1-arylmethyl)-1,3-butadienes

  摘要：

  Chiral 1-arylpropargyl amides, which are resistant to undergoing ethylene-alkyne cross-metathesis at atmospheric pressure, were reacted under microwave irradiation to afford enantiomerically enriched 2-(N-1-acetyl-1-arylmethyl)-1,3-butadienes within a few minutes. Enantiomerically enriched amides underwent ethylene-alkyne cross-metathesis with retention of configuration at the propargylic/allylic position. A series of chiral 2-(N-1-acetyl-1-arylmethyl)-1,3-butadienes were synthesised with ee >= 95%; these latter compounds could be used as building blocks for the synthesis of new antifungal and antiaromatase agents. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.08.002

文献信息

• Synthesis and biological evaluation of new enantiomerically pure azole derivatives as inhibitors of Mycobacterium tuberculosis
  作者：Daniele Castagnolo、Marco Radi、Filippo Dessì、Fabrizio Manetti、Manuela Saddi、Rita Meleddu、Alessandro De Logu、Maurizio Botta

  DOI：10.1016/j.bmcl.2009.02.101

  日期：2009.4

  A series of novel enantiomerically pure azole derivatives was synthesized. The new compounds, bearing both an imidazole as well as a triazole moiety, were evaluated as antimycobacterial agents. One of them proved to have activity against Mycobaterium tuberculosis comparable to those of the classical antibacterial/antifungal drugs Econazole and Clotrimazole.

  合成了一系列新颖的对映体纯的唑衍生物。同时带有咪唑和三唑部分的新化合物被评估为抗分枝杆菌剂。其中一种被证明具有与经典的抗菌/抗真菌药益康唑和克霉唑相当的抗结核分枝杆菌的活性。