(2S,3S)-2-(phenylmethoxymethyl)-3-(4-phenylphenyl)oxirane | 937795-11-4

• 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: (2S,3S)-2-(phenylmethoxymethyl)-3-(4-phenylphenyl)oxirane
• CAS: 937795-11-4
• 化学式: C₂₂H₂₀O₂
• 分子量: 316.4
• InChiKey: NDNGOTJRMLBJNV-VXKWHMMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  21.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S,3S)-2-(phenylmethoxymethyl)-3-(4-phenylphenyl)oxirane 在 ammonium hydroxide 、 lithium perchlorate 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 以76%的产率得到(1R,2R)-1-amino-3-phenylmethoxy-1-(4-phenylphenyl)propan-2-ol
  参考文献：
  名称：

  Suzuki Cross-Coupling on Enantiomerically Pure Epoxides:  Efficient Synthesis of Diverse, Modular Amino Alcohols from Single Enantiopure Precursors

  摘要：

  Suzuki arylation of enantiopure (4-bromophenyl)- or (3,5-dibromophenyl)glycidyl ethers has been achieved in toluene under Buchwald conditions [ArB(OH)(2) (1.1 equiv), Cs2CO3 (2 equiv), Pd-2(dba)(3)center dot C6H6 (1 mol %), S-Phos (4 mol %), toluene, 100 degrees C] allowing for the formation of modular arylglycidyl ethers not directly available in enantiopure form by epoxidation routes. These bulky ethers, when submitted to regioselective and stereospecific ring opening with ammonia [aq NH3, LiClO4 (1 equiv), THF, microwave irradiation (80 W), 125 degrees C] in a sealed tube, provide access to novel enantiopure beta-amino alcohols which, in turn, provide an easy access to structurally complex C-2 symmetrical bisoxazolines.

  DOI：

  10.1021/jo062612t
• 作为产物：
  描述：

  [(2S,3S)-3-(4-溴苯基)环氧乙烷-2-基]甲醇 在 [Pd₂(dba)₃](C₆H₆) 2-双环己基膦-2',6'-二甲氧基联苯 、 sodium hydride 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 9.0h， 生成 (2S,3S)-2-(phenylmethoxymethyl)-3-(4-phenylphenyl)oxirane
  参考文献：
  名称：

  Suzuki Cross-Coupling on Enantiomerically Pure Epoxides:  Efficient Synthesis of Diverse, Modular Amino Alcohols from Single Enantiopure Precursors

  摘要：

  Suzuki arylation of enantiopure (4-bromophenyl)- or (3,5-dibromophenyl)glycidyl ethers has been achieved in toluene under Buchwald conditions [ArB(OH)(2) (1.1 equiv), Cs2CO3 (2 equiv), Pd-2(dba)(3)center dot C6H6 (1 mol %), S-Phos (4 mol %), toluene, 100 degrees C] allowing for the formation of modular arylglycidyl ethers not directly available in enantiopure form by epoxidation routes. These bulky ethers, when submitted to regioselective and stereospecific ring opening with ammonia [aq NH3, LiClO4 (1 equiv), THF, microwave irradiation (80 W), 125 degrees C] in a sealed tube, provide access to novel enantiopure beta-amino alcohols which, in turn, provide an easy access to structurally complex C-2 symmetrical bisoxazolines.

  DOI：

  10.1021/jo062612t

文献信息

• Suzuki Cross-Coupling on Enantiomerically Pure Epoxides:  Efficient Synthesis of Diverse, Modular Amino Alcohols from Single Enantiopure Precursors
  作者：Xavier Cattoën、Miquel A. Pericàs

  DOI：10.1021/jo062612t

  日期：2007.4.1

  Suzuki arylation of enantiopure (4-bromophenyl)- or (3,5-dibromophenyl)glycidyl ethers has been achieved in toluene under Buchwald conditions [ArB(OH)(2) (1.1 equiv), Cs2CO3 (2 equiv), Pd-2(dba)(3)center dot C6H6 (1 mol %), S-Phos (4 mol %), toluene, 100 degrees C] allowing for the formation of modular arylglycidyl ethers not directly available in enantiopure form by epoxidation routes. These bulky ethers, when submitted to regioselective and stereospecific ring opening with ammonia [aq NH3, LiClO4 (1 equiv), THF, microwave irradiation (80 W), 125 degrees C] in a sealed tube, provide access to novel enantiopure beta-amino alcohols which, in turn, provide an easy access to structurally complex C-2 symmetrical bisoxazolines.