1-((2-iodoethoxy)methyl)-4-(4,4,4-trifluorobutoxy)benzene | 1350642-13-5

• 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: 1-((2-iodoethoxy)methyl)-4-(4,4,4-trifluorobutoxy)benzene
• 英文别名: 1-(2-Iodoethoxymethyl)-4-(4,4,4-trifluorobutoxy)benzene
• CAS: 1350642-13-5
• 化学式: C₁₃H₁₆F₃IO₂
• 分子量: 388.169
• InChiKey: NDIGLAZRSBKAPL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-((2-iodoethoxy)methyl)-4-(4,4,4-trifluorobutoxy)benzene 、 丙酰胺,N-[(1R,2R)-2-羟基-1-甲基-2-苯基乙基]-N-甲基- 在 正丁基锂 、 二异丙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 13.58h， 以95%的产率得到(S)-4-(4-(4,4,4-trifluorobutoxy)benzyloxy)-N-((1R,2R)-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
• 作为产物：
  描述：

  4-(4,4,4-trifluorobutoxy)benzaldehyde 在 咪唑 、 sodium tetrahydroborate 、 碘 、 三溴化磷 、 sodium hydride 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 mineral oil 为溶剂， 反应 17.5h， 生成 1-((2-iodoethoxy)methyl)-4-(4,4,4-trifluorobutoxy)benzene
  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