3-hydroxy-2,2-dimethyl-3-phenyl-N-prop-2-ynylpropanamide | 1058628-79-7

• 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: 3-hydroxy-2,2-dimethyl-3-phenyl-N-prop-2-ynylpropanamide
• CAS: 1058628-79-7
• 化学式: C₁₄H₁₇NO₂
• 分子量: 231.294
• InChiKey: QCWBPDLETYOHDS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R,5R)-1-aza-2-(tert-butyl)-7,7-dimethyl-6,8-dioxo-5-methoxycarbonyl-3-oxabicyclo[3.3.0]octane 、 3-hydroxy-2,2-dimethyl-3-phenyl-N-prop-2-ynylpropanamide 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 以14%的产率得到methyl (3R,7S,7aR)-3-tert-butyl-7-hydroxy-7-[3-[(3-hydroxy-2,2-dimethyl-3-phenylpropanoyl)amino]prop-1-ynyl]-6,6-dimethyl-5-oxo-1,3-dihydropyrrolo[1,2-c][1,3]oxazole-7a-carboxylate
  参考文献：
  名称：

  Oxazolomycins: Natural product lead structures for novel antibacterials by click fragment conjugation

  摘要：

  Conjugation of amide and lactam subunits by a 'Click' type approach provides access to structural mimics of the oxazolomycin series of natural products, some of which exhibit antibacterial activity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.02.066
• 作为产物：
  描述：

  (+/-)-3,3-Dimethyl-4-phenyl-2-oxetanone 、 炔丙胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以92%的产率得到3-hydroxy-2,2-dimethyl-3-phenyl-N-prop-2-ynylpropanamide
  参考文献：
  名称：

  On the antibiotic activity of oxazolomycin

  摘要：

  Structural analysis of oxazolomycin and simpler fragments containing a common 3-hydroxy-2,2-dimethylpropanamide moiety has indicated that a U-shaped conformation is preferred, in some cases stabilised by hydrogen bonding between the N-H and O-H residues, as shown by a combination of molecular modelling, NMR spectroscopic and single crystal X-ray analysis. A direct synthesis of this unit has been established via the opening of b-lactones by a range of amines, and their antibacterial activity been shown to vary with the hydrophobic character of the substituents. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.05.105

文献信息

• On the antibiotic activity of oxazolomycin
  作者：Claire L. Bagwell、Mark G. Moloney、Amber L. Thompson

  DOI：10.1016/j.bmcl.2008.05.105

  日期：2008.7

  Structural analysis of oxazolomycin and simpler fragments containing a common 3-hydroxy-2,2-dimethylpropanamide moiety has indicated that a U-shaped conformation is preferred, in some cases stabilised by hydrogen bonding between the N-H and O-H residues, as shown by a combination of molecular modelling, NMR spectroscopic and single crystal X-ray analysis. A direct synthesis of this unit has been established via the opening of b-lactones by a range of amines, and their antibacterial activity been shown to vary with the hydrophobic character of the substituents. (c) 2008 Elsevier Ltd. All rights reserved.
• Oxazolomycins: Natural product lead structures for novel antibacterials by click fragment conjugation
  作者：Claire L. Bagwell、Mark G. Moloney、Muhammad Yaqoob

  DOI：10.1016/j.bmcl.2010.02.066

  日期：2010.4

  Conjugation of amide and lactam subunits by a 'Click' type approach provides access to structural mimics of the oxazolomycin series of natural products, some of which exhibit antibacterial activity. (C) 2010 Elsevier Ltd. All rights reserved.