2-{(S)-2-[(S)-2-(2-Hydroxy-ethoxy)-1-methyl-ethoxy]-propoxy}-ethanol | 857682-57-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-{(S)-2-[(S)-2-(2-Hydroxy-ethoxy)-1-methyl-ethoxy]-propoxy}-ethanol
• 英文别名: 2-[(2S)-2-[(2S)-1-(2-hydroxyethoxy)propan-2-yl]oxypropoxy]ethanol
• CAS: 857682-57-6
• 化学式: C₁₀H₂₂O₅
• 分子量: 222.282
• InChiKey: OPOLDAGUHVYFTL-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  15
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  2-{(S)-2-[(S)-2-(2-Hydroxy-ethoxy)-1-methyl-ethoxy]-propoxy}-ethanol 在 palladium on activated charcoal 叔丁基锂 、 sodium hydride 、 对甲苯磺酸 、 氟硼酸钾 作用下， 以 四氢呋喃 、 乙醇 、 水 、 N,N-二甲基甲酰胺 、 正戊烷 为溶剂， 反应 16.5h， 生成 3,3-Bis-((8S,10S)-21-hydroxy-8,10-dimethyl-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：

  (7S,9S)-7,9-dimethyl-1,15-diphenyl-2,5,8,11,14-pentaoxapentadecane 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 2.0h， 生成 2-{(S)-2-[(S)-2-(2-Hydroxy-ethoxy)-1-methyl-ethoxy]-propoxy}-ethanol
  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

文献信息

• Visual Enantiomeric Recognition of Amino Acid Derivatives in Protic Solvents¹^,
  作者：Kazunori Tsubaki、Daisuke Tanima、Mohammad Nuruzzaman、Tomokazu Kusumoto、Kaoru Fuji、Takeo Kawabata

  DOI：10.1021/jo050387u

  日期：2005.6.1

  [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.