3,3-Bis-((7S,11S)-21-allyloxy-7,11-dimethyl-3,6,9,12,15-pentaoxa-bicyclo[15.3.1]henicosa-1(20),17(21),18-trien-19-yl)-3H-isobenzofuran-1-one | 857682-65-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 3,3-Bis-((7S,11S)-21-allyloxy-7,11-dimethyl-3,6,9,12,15-pentaoxa-bicyclo[15.3.1]henicosa-1(20),17(21),18-trien-19-yl)-3H-isobenzofuran-1-one
• 英文别名: 3,3-bis[(7S,11S)-7,11-dimethyl-21-prop-2-enoxy-3,6,9,12,15-pentaoxabicyclo[15.3.1]henicosa-1(20),17(21),18-trien-19-yl]-2-benzofuran-1-one
• CAS: 857682-65-6
• 化学式: C₅₀H₆₆O₁₄
• 分子量: 891.066
• InChiKey: KZSYXTIECALBPL-ZQWQDMLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  64
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  137
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  3,3-Bis-((7S,11S)-21-allyloxy-7,11-dimethyl-3,6,9,12,15-pentaoxa-bicyclo[15.3.1]henicosa-1(20),17(21),18-trien-19-yl)-3H-isobenzofuran-1-one 在 palladium on activated charcoal 对甲苯磺酸 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 以93%的产率得到3,3-Bis-((7S,11S)-21-hydroxy-7,11-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：

  Benzene, 5-bromo-1,3-bis(chloromethyl)-2-(2-propenyloxy)- 在 叔丁基锂 、 sodium hydride 、 氟硼酸钾 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 正戊烷 为溶剂， 反应 14.5h， 生成 3,3-Bis-((7S,11S)-21-allyloxy-7,11-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