3,3,3-trifluoropropanoic acid trifluoromethyl ester | 93667-89-1

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代烷
• 英文名称: 3,3,3-trifluoropropanoic acid trifluoromethyl ester
• 英文别名: 3,3,3-trifluoropropionic acid trifluoromethyl ester；trifluoromethyl 3,3,3-trifluoropropionate；Trifluoromethyl 3,3,3-trifluoropropanoate；trifluoromethyl 3,3,3-trifluoropropanoate
• CAS: 93667-89-1
• 化学式: C₄H₂F₆O₂
• 分子量: 196.049
• InChiKey: HRADOMFTXBAHOC-UHFFFAOYSA-N

物化性质

• 沸点：
  79.2±40.0 °C(Predicted)
• 密度：
  1.498±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3,3,3-trifluoropropanoic acid trifluoromethyl ester 、 长春布宁 在 lithium hexamethyldisilazane 、 18-冠醚-6 、 potassium carbonate 作用下， 以 四氢呋喃 、 苯 为溶剂， 以28%的产率得到(-)-15-methylene-eburnamonine
  参考文献：
  名称：

  Synthesis of 15-methylene-eburnamonine from (+)-vincamine, evaluation of anticancer activity, and investigation of mechanism of action by quantitative NMR

  摘要：

  The biological role of installing a critical exocyclic enone into the structure of the alkaloid, (-)-eburnamonine, and characterization of the new chemical reactivity by quantitative NMR without using deuterated solvents are described. This selective modification to a natural product imparts potent anticancer activity as well as bestows chemical reactivity toward nucleophilic thiols, which was measured by quantitative NMR. The synthetic strategy provides an overall conversion of 40%. In the key synthetic step, a modified Peterson olefination was accomplished through the facile release of trifluoroacetate to create the requisite enone in the presence of substantial steric hindrance. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.08.095

文献信息

• Synthesis of 15-methylene-eburnamonine from (+)-vincamine, evaluation of anticancer activity, and investigation of mechanism of action by quantitative NMR
  作者：James R. Woods、Mark V. Riofski、Mary M. Zheng、Melissa A. O’Banion、Huaping Mo、Julia Kirshner、David A. Colby

  DOI：10.1016/j.bmcl.2013.08.095

  日期：2013.11

  The biological role of installing a critical exocyclic enone into the structure of the alkaloid, (-)-eburnamonine, and characterization of the new chemical reactivity by quantitative NMR without using deuterated solvents are described. This selective modification to a natural product imparts potent anticancer activity as well as bestows chemical reactivity toward nucleophilic thiols, which was measured by quantitative NMR. The synthetic strategy provides an overall conversion of 40%. In the key synthetic step, a modified Peterson olefination was accomplished through the facile release of trifluoroacetate to create the requisite enone in the presence of substantial steric hindrance. (C) 2013 Elsevier Ltd. All rights reserved.