[(1R,2S)-2-[4-[5-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecylsulfanyl)pentyl]phenyl]-2-hydroxy-1,2-diphenylethyl] prop-2-enoate | 1101254-68-5

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: [(1R,2S)-2-[4-[5-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecylsulfanyl)pentyl]phenyl]-2-hydroxy-1,2-diphenylethyl] prop-2-enoate
• CAS: 1101254-68-5
• 化学式: C₃₈H₃₃F₁₇O₃S
• 分子量: 892.717
• InChiKey: VALZCBIGVHNZGJ-VEEOACQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.9
• 重原子数：
  59
• 可旋转键数：
  22
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  71.8
• 氢给体数：
  1
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  环戊基甲醛 、 [(1R,2S)-2-[4-[5-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecylsulfanyl)pentyl]phenyl]-2-hydroxy-1,2-diphenylethyl] prop-2-enoate 在 samarium diiodide 作用下， 以 叔丁醇 为溶剂， 反应 5.0h， 生成 (S)-5-cyclopentyldihydrofuran-2(3H)-one 、 (R)-5-cyclopentyldihydrofuran-2(3H)-one 、 (1S,2R)-1-{4-[5-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecylsulfanyl)pentyl]-phenyl}-1,2-diphenylethane-1,2-diol
  参考文献：
  名称：

  An asymmetric, SmI2-mediated approach to γ-butyrolactones using a new, fluorous-tagged auxiliary

  摘要：

  A new, fluorous-tagged chiral auxiliary has been developed for the asymmetric, SmI2-mediated coupling of aldehydes and alpha,beta-unsaturated esters. gamma-Butyrolactones are obtained in moderate to good isolated yield and in high enantiomeric excess. The fluorous tag allows the auxiliary to be conveniently recovered by fluorous solid-phase extraction (FSPE) and reused. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.08.110
• 作为产物：
  描述：

  (1S,2R)-1-{4-[5-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecylsulfanyl)pentyl]-phenyl}-1,2-diphenylethane-1,2-diol 、 丙烯酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以65%的产率得到[(1R,2S)-2-[4-[5-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecylsulfanyl)pentyl]phenyl]-2-hydroxy-1,2-diphenylethyl] prop-2-enoate
  参考文献：
  名称：

  An asymmetric, SmI2-mediated approach to γ-butyrolactones using a new, fluorous-tagged auxiliary

  摘要：

  A new, fluorous-tagged chiral auxiliary has been developed for the asymmetric, SmI2-mediated coupling of aldehydes and alpha,beta-unsaturated esters. gamma-Butyrolactones are obtained in moderate to good isolated yield and in high enantiomeric excess. The fluorous tag allows the auxiliary to be conveniently recovered by fluorous solid-phase extraction (FSPE) and reused. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.08.110

文献信息

• An asymmetric, SmI2-mediated approach to γ-butyrolactones using a new, fluorous-tagged auxiliary
  作者：Johannes C. Vogel、Rebecca Butler、David J. Procter

  DOI：10.1016/j.tet.2008.08.110

  日期：2008.12

  A new, fluorous-tagged chiral auxiliary has been developed for the asymmetric, SmI2-mediated coupling of aldehydes and alpha,beta-unsaturated esters. gamma-Butyrolactones are obtained in moderate to good isolated yield and in high enantiomeric excess. The fluorous tag allows the auxiliary to be conveniently recovered by fluorous solid-phase extraction (FSPE) and reused. (C) 2008 Elsevier Ltd. All rights reserved.