(1S)-2-[[5-bromo-3-[[(2S)-2-hydroxy-2-phenylethoxy]methyl]-2-prop-2-enoxyphenyl]methoxy]-1-phenylethanol | 857682-69-0

• 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: (1S)-2-[[5-bromo-3-[[(2S)-2-hydroxy-2-phenylethoxy]methyl]-2-prop-2-enoxyphenyl]methoxy]-1-phenylethanol
• CAS: 857682-69-0
• 化学式: C₂₇H₂₉BrO₅
• 分子量: 513.428
• InChiKey: RVCAWLNYKIJXOQ-CLJLJLNGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  33
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S)-2-[[5-bromo-3-[[(2S)-2-hydroxy-2-phenylethoxy]methyl]-2-prop-2-enoxyphenyl]methoxy]-1-phenylethanol 在 四(三苯基膦)钯 sodium tetrahydroborate 、 叔丁基锂 、 sodium hydride 、 氟硼酸钾 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 正戊烷 为溶剂， 反应 41.5h， 生成 3,3-Bis-((5S,13S)-21-hydroxy-5,13-diphenyl-3,6,9,12,15-pentaoxa-bicyclo[15.3.1]henicosa-1(20),17(21),18-trien-19-yl)-3H-isobenzofuran-1-one
  参考文献：
  名称：

  Visual Enantiomeric Recognition of Amino Acid Derivatives in Protic Solvents^1,

  摘要：

  [GRAPHICS]Various types of chiral host molecules 2-7 based on a phenolphthalein skeleton and two crown ethers were prepared for use in visual enantiomeric recognition, and we examined their enantioselective coloration in complexation with chiral amino acid derivatives 9-22 in methanol solution. Methyl-substituted host (S,S,S,S)-3 showed particularly prominent enantiomer selectivity for the alanine amide derivatives 11 and 12. A combination of methyl-substituted host (S,S,S,S)-3 with guest (R)-11 or (R)-12 developed a purple color, whereas no color development was observed with (S)-11 or (S)-12. On the other hand, phenyl-substituted host (S,S,S,S)-6 showed deeper coloration with a wide range of (S)-beta-amino alcohols compared to that seen with host (S,S,S,S)-6 and the corresponding (R)-beta-amino alcohols at 0 degrees C. Furthermore, absorbance inversion temperatures (AIT) were observed within the range of 0-50 degrees C in many cases.

  DOI：

  10.1021/jo050387u
• 作为产物：
  描述：

  (S)-(+)-2-phenyl-2-(tetrahydropyranyloxy)ethanol 在 盐酸 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 (1S)-2-[[5-bromo-3-[[(2S)-2-hydroxy-2-phenylethoxy]methyl]-2-prop-2-enoxyphenyl]methoxy]-1-phenylethanol
  参考文献：
  名称：

  Visual Enantiomeric Recognition of Amino Acid Derivatives in Protic Solvents^1,

  摘要：

  [GRAPHICS]Various types of chiral host molecules 2-7 based on a phenolphthalein skeleton and two crown ethers were prepared for use in visual enantiomeric recognition, and we examined their enantioselective coloration in complexation with chiral amino acid derivatives 9-22 in methanol solution. Methyl-substituted host (S,S,S,S)-3 showed particularly prominent enantiomer selectivity for the alanine amide derivatives 11 and 12. A combination of methyl-substituted host (S,S,S,S)-3 with guest (R)-11 or (R)-12 developed a purple color, whereas no color development was observed with (S)-11 or (S)-12. On the other hand, phenyl-substituted host (S,S,S,S)-6 showed deeper coloration with a wide range of (S)-beta-amino alcohols compared to that seen with host (S,S,S,S)-6 and the corresponding (R)-beta-amino alcohols at 0 degrees C. Furthermore, absorbance inversion temperatures (AIT) were observed within the range of 0-50 degrees C in many cases.

  DOI：

  10.1021/jo050387u