(R)-4-(4-(4,4,5,5,6,6,7,7,7-nonafluoroheptyloxy)benzyloxy)-N-((1S,2S)-1-hydroxy-1-phenylpropan-2-yl)-N,2-dimethylbutanamide | 1350642-16-8

• 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: (R)-4-(4-(4,4,5,5,6,6,7,7,7-nonafluoroheptyloxy)benzyloxy)-N-((1S,2S)-1-hydroxy-1-phenylpropan-2-yl)-N,2-dimethylbutanamide
• 英文别名: (2R)-N-[(1S,2S)-1-hydroxy-1-phenylpropan-2-yl]-N,2-dimethyl-4-[[4-(4,4,5,5,6,6,7,7,7-nonafluoroheptoxy)phenyl]methoxy]butanamide
• CAS: 1350642-16-8
• 化学式: C₂₉H₃₄F₉NO₄
• 分子量: 631.579
• InChiKey: QSKJHZAIVIBUEH-JXALWOEJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  43
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  1-bromomethyl-4-(4,4,5,5,6,6,7,7,7-nonafluoroheptyloxy)benzene 在 咪唑 、 正丁基锂 、 碘 、 sodium hydride 、 二异丙胺 、 三苯基膦 、 lithium chloride 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 mineral oil 为溶剂， 反应 26.08h， 生成 (R)-4-(4-(4,4,5,5,6,6,7,7,7-nonafluoroheptyloxy)benzyloxy)-N-((1S,2S)-1-hydroxy-1-phenylpropan-2-yl)-N,2-dimethylbutanamide
  参考文献：
  名称：

  Synthesis and Spectroscopic Analysis of a Stereoisomer Library of the Phytophthora Mating Hormone α1 and Derived Bis-Mosher Esters

  摘要：

  Fluorous mixture synthesis provided all eight diastereomers of the phytophthora hormone alpha 1 with the R configuration at C11 as individual samples after demixing and detagging. The library of all possible bis-Mosher esters (16) was then made by esterification. Complete sets of H-1, C-13, and (for the Mosher esters) F-19 NMR spectra were recorded, assigned, and compared with each other and with published spectra. Not all of the spectra are unique, and the H-1 NMR spectra of the Mosher esters provided the most information. The previous assignment of the natural sample as an "all-R" stereoisomer mixed with its 3S-epimer was confirmed.

  DOI：

  10.1021/ja2082679

文献信息

• Synthesis and Spectroscopic Analysis of a Stereoisomer Library of the Phytophthora Mating Hormone α1 and Derived Bis-Mosher Esters
  作者：Reena Bajpai、Dennis P. Curran

  DOI：10.1021/ja2082679

  日期：2011.12.21

  Fluorous mixture synthesis provided all eight diastereomers of the phytophthora hormone alpha 1 with the R configuration at C11 as individual samples after demixing and detagging. The library of all possible bis-Mosher esters (16) was then made by esterification. Complete sets of H-1, C-13, and (for the Mosher esters) F-19 NMR spectra were recorded, assigned, and compared with each other and with published spectra. Not all of the spectra are unique, and the H-1 NMR spectra of the Mosher esters provided the most information. The previous assignment of the natural sample as an "all-R" stereoisomer mixed with its 3S-epimer was confirmed.