(R)-2-(3-Allyloxy-phenyl)-2-amino-ethanol | 185112-17-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (R)-2-(3-Allyloxy-phenyl)-2-amino-ethanol
• CAS: 185112-17-8
• 化学式: C₁₁H₁₅NO₂
• 分子量: 193.246
• InChiKey: NLAFUVUSNNLIQZ-NSHDSACASA-N

物化性质

• 沸点：
  348.1±37.0 °C(Predicted)
• 密度：
  1.096±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.24
• 重原子数：
  14.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  55.48
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (R)-2-(3-Allyloxy-phenyl)-2-amino-ethanol 在 2,6-二甲基吡啶 、 盐酸 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 四(三苯基膦)钯 、 二苯基磷酸 、 三氯化硼 、 氯化铵 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 、 cesium fluoride 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.75h， 生成 2-(3-fluoro-4-nitrophenyl)-N-[(8R,11S,14R)-8-(hydroxymethyl)-11-(3-hydroxyphenyl)-18-nitro-10,13-dioxo-2-oxa-9,12-diazatricyclo[14.2.2.13,7]henicosa-1(18),3,5,7(21),16,19-hexaen-14-yl]acetamide
  参考文献：
  名称：

  Synthesis of Modified Carboxyl Binding Pockets of Vancomycin and Teicoplanin

  摘要：

  Sixteen-membered macrocycle 3 and 16+14 bicyclic compound 4, incorporating a terminal primary hydroxyl group in the peptide sequence, have been designed and synthesized. The syntheses feature the use of an efficient cycloetherification based on an intramolecular SNAr reaction for the formation of biaryl ether bonds. Cyclization of linear tetrapeptide 30, prepared via a convergent [2+2] segment coupling between 26 and 29, gave macrocycle 31 (P configuration) as a single isolable atropisomer. Removal of the Boc protecting group afforded the modified carboxyl binding pocket of vancomycin 3. A sequential 2-fold intramolecular SNAr reaction has been used to construct the model bicyclic system (i.e. 4) of the D-O-E-F-O-G ring of teicoplanin. Cyclization conditions (CsF, DMF, room temperature) are sufficiently mild that the configuration of the racemization-prone arylglycine residue was not affected. Chiral building blocks such as D-(1R)-[2-[(tert-butyldimethylsilyl)oxy] 1-[3-(allyloxy)phenyl]ethyl]amine 16, and L-(S)-N-Boc-[3-(isopropyloxy)phenyl]glycine (32) were synthesized employing Evans' asymmetric azidation method, while L-(S)-4-fluoro-3-nitrophenylalanine methyl ester 23 was prepared using Schollkopf's bislactim ether as chiral glycine template. Compound 3 showed interesting conformational properties compared to vancomycin and its binding with Ac-D-Ala was studied by NMR titration experiments. A dissociation constant (K-d = 5 x 10(-4)) was calculated by a curve fitting method. Compound 4 is currently the most advanced synthetic intermediate toward the total synthesis of teicoplanin.

  DOI：

  10.1021/jo961412m
• 作为产物：
  描述：

  在 锂硼氢 、 tin(ll) chloride 作用下， 以 甲醇 为溶剂， 反应 16.0h， 生成 (R)-2-(3-Allyloxy-phenyl)-2-amino-ethanol
  参考文献：
  名称：

  Synthesis of Modified Carboxyl Binding Pockets of Vancomycin and Teicoplanin

  摘要：

  Sixteen-membered macrocycle 3 and 16+14 bicyclic compound 4, incorporating a terminal primary hydroxyl group in the peptide sequence, have been designed and synthesized. The syntheses feature the use of an efficient cycloetherification based on an intramolecular SNAr reaction for the formation of biaryl ether bonds. Cyclization of linear tetrapeptide 30, prepared via a convergent [2+2] segment coupling between 26 and 29, gave macrocycle 31 (P configuration) as a single isolable atropisomer. Removal of the Boc protecting group afforded the modified carboxyl binding pocket of vancomycin 3. A sequential 2-fold intramolecular SNAr reaction has been used to construct the model bicyclic system (i.e. 4) of the D-O-E-F-O-G ring of teicoplanin. Cyclization conditions (CsF, DMF, room temperature) are sufficiently mild that the configuration of the racemization-prone arylglycine residue was not affected. Chiral building blocks such as D-(1R)-[2-[(tert-butyldimethylsilyl)oxy] 1-[3-(allyloxy)phenyl]ethyl]amine 16, and L-(S)-N-Boc-[3-(isopropyloxy)phenyl]glycine (32) were synthesized employing Evans' asymmetric azidation method, while L-(S)-4-fluoro-3-nitrophenylalanine methyl ester 23 was prepared using Schollkopf's bislactim ether as chiral glycine template. Compound 3 showed interesting conformational properties compared to vancomycin and its binding with Ac-D-Ala was studied by NMR titration experiments. A dissociation constant (K-d = 5 x 10(-4)) was calculated by a curve fitting method. Compound 4 is currently the most advanced synthetic intermediate toward the total synthesis of teicoplanin.

  DOI：

  10.1021/jo961412m