(1R,3Z)-5,5,5-trifluoro-1-(methoxymethoxy)-1-phenylpent-3-en-2-yl pivalate

• 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: (1R,3Z)-5,5,5-trifluoro-1-(methoxymethoxy)-1-phenylpent-3-en-2-yl pivalate
• 英文别名: [(Z,1R)-5,5,5-trifluoro-1-(methoxymethoxy)-1-phenylpent-3-en-2-yl] 2,2-dimethylpropanoate
• 化学式: C₁₈H₂₃F₃O₄
• 分子量: 360.373
• InChiKey: YKKVSTGEFHCYOF-SJNAXNHNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1R,3Z)-5,5,5-trifluoro-1-(methoxymethoxy)-1-phenylpent-3-en-2-yl pivalate 在 二甲基硫 、 三氟化硼乙醚 作用下， 以 正己烷 为溶剂， 反应 2.0h， 以96%的产率得到(1R,2S,3Z)-5,5,5-trifluoro-1-phenyl-2-(pivaloyloxy)pent-3-en-1-ol
  参考文献：
  名称：

  Construction of chiral trifluoromethylated materials by combination of stereochemically predictable SN2′ reaction and Ireland-Claisen rearrangement

  摘要：

  We have succeeded in establishment of a novel route for the construction of optically active CF3-containing carboxylic acids in a stereochemically predictable manner starting from easily available mandelic acid by convenient combination of the copper-mediated anti-S(N)2' type substitution and lreland-Claisen rearrangement. (c) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2012.10.013

文献信息

• Construction of chiral trifluoromethylated materials by combination of stereochemically predictable SN2′ reaction and Ireland-Claisen rearrangement
  作者：Tomoaki Ichikawa、Tomoko Kawasaki-Takasuka、Shigeyuki Yamada、Takashi Yamazaki、Toshio Kubota

  DOI：10.1016/j.jfluchem.2012.10.013

  日期：2013.8

  We have succeeded in establishment of a novel route for the construction of optically active CF3-containing carboxylic acids in a stereochemically predictable manner starting from easily available mandelic acid by convenient combination of the copper-mediated anti-S(N)2' type substitution and lreland-Claisen rearrangement. (c) 2012 Elsevier B.V. All rights reserved.