(+/-)-trifluoromethanesulfonic acid 6-(1-ethylpropyl)-3-fluorotetrahydropyran-4-yl ester

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: (+/-)-trifluoromethanesulfonic acid 6-(1-ethylpropyl)-3-fluorotetrahydropyran-4-yl ester
• 英文别名: [(2R,4R,5S)-5-fluoro-2-pentan-3-yloxan-4-yl] trifluoromethanesulfonate
• 化学式: C₁₁H₁₈F₄O₄S
• 分子量: 322.321
• InChiKey: FZHWZGDYACWWLJ-IVZWLZJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2-乙基丁醛 、 三氟甲磺酸三甲基硅酯 、 2-fluoro-but-3-en-1-ol 以 二氯甲烷 为溶剂， 反应 0.5h， 以52%的产率得到(+/-)-trifluoromethanesulfonic acid 6-(1-ethylpropyl)-3-fluorotetrahydropyran-4-yl ester
  参考文献：
  名称：

  On the choice of Lewis acids for the Prins reaction; two total syntheses of (±)-Civet

  摘要：

  While developing new variations of the Prins cyclisation reaction, the effect of the choice of Lewis acid on the outcome of the reaction and the product(s) has been investigated, yielding hitherto unseen dihydropyran products in the Prins cyclisation reaction of homoallylic alcohols, and two new modifications of the reaction: the triflate-trapped Prins adduct and the Mukaiyama-Aldol-silyl-Prins reaction. Two of these methods are employed in two complementary total syntheses of the important perfumery compound, (+/-)-Civet. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.019

文献信息

• On the choice of Lewis acids for the Prins reaction; two total syntheses of (±)-Civet
  作者：Freda K. Chio、Julie Warne、Damien Gough、Mark Penny、Sasa Green (née Martinović)、Simon J. Coles、Mike B. Hursthouse、Peter Jones、Lorraine Hassall、Thomas M. McGuire、Adrian P. Dobbs

  DOI：10.1016/j.tet.2011.05.019

  日期：2011.7

  While developing new variations of the Prins cyclisation reaction, the effect of the choice of Lewis acid on the outcome of the reaction and the product(s) has been investigated, yielding hitherto unseen dihydropyran products in the Prins cyclisation reaction of homoallylic alcohols, and two new modifications of the reaction: the triflate-trapped Prins adduct and the Mukaiyama-Aldol-silyl-Prins reaction. Two of these methods are employed in two complementary total syntheses of the important perfumery compound, (+/-)-Civet. (C) 2011 Elsevier Ltd. All rights reserved.