2-(2-bromomethylphenyl)-(4S)-4-methyl-4,5-dihydrooxazole | 945621-94-3

• 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: 2-(2-bromomethylphenyl)-(4S)-4-methyl-4,5-dihydrooxazole
• 英文别名: (4S)-2-[2-(bromomethyl)phenyl]-4-methyl-4,5-dihydro-1,3-oxazole
• CAS: 945621-94-3
• 化学式: C₁₁H₁₂BrNO
• 分子量: 254.126
• InChiKey: VPDYOOXQLZMPCH-QMMMGPOBSA-N

物化性质

• 熔点：
  83-84 °C
• 沸点：
  347.2±25.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-bromomethylphenyl)-(4S)-4-methyl-4,5-dihydrooxazole 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 (3aR,8aR)-N-benzyl-2,2-dimethyl-N-[[2-[(4S)-4-methyl-4,5-dihydro-1,3-oxazol-2-yl]phenyl]methyl]-4,4,8,8-tetraphenyl-3a,8a-dihydro-[1,3]dioxolo[4,5-e][1,3,2]dioxaphosphepin-6-amine
  参考文献：
  名称：

  Aminophosphine–oxazoline and phosphoramidite–oxazoline ligands and their application in asymmetric catalysis

  摘要：

  The synthesis of a novel series of aminophosphine-oxazoline and phosphoramidite-oxazoline is described. The efficacy of these aminophosphine-oxazoline ligands was investigated in the palladium catalysed asymmetric allylic alkylation of 1,3-diphenylprop-2-enyl acetate leading to a maximum of 38% ee at 64% conversion. Phosphoramidite-oxazoline ligands, however, gave ees of up to 87% at 71% conversion in the same reaction and also proved to be effective in the palladium catalysed asymmetric Suzuki coupling between 2-methylnaphthylboronic acid and 1-bromonaphthalene, leading to a maximum of 46% ee in 54% isolated yield at room temperature. (C) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2007.04.020
• 作为产物：
  描述：

  L-氨基丙醇 、 2-氰基溴苄 在 zinc(II) chloride 作用下， 以 乙醚 、 氯苯 为溶剂， 反应 24.0h， 以42%的产率得到2-(2-bromomethylphenyl)-(4S)-4-methyl-4,5-dihydrooxazole
  参考文献：
  名称：

  Aminophosphine–oxazoline and phosphoramidite–oxazoline ligands and their application in asymmetric catalysis

  摘要：

  The synthesis of a novel series of aminophosphine-oxazoline and phosphoramidite-oxazoline is described. The efficacy of these aminophosphine-oxazoline ligands was investigated in the palladium catalysed asymmetric allylic alkylation of 1,3-diphenylprop-2-enyl acetate leading to a maximum of 38% ee at 64% conversion. Phosphoramidite-oxazoline ligands, however, gave ees of up to 87% at 71% conversion in the same reaction and also proved to be effective in the palladium catalysed asymmetric Suzuki coupling between 2-methylnaphthylboronic acid and 1-bromonaphthalene, leading to a maximum of 46% ee in 54% isolated yield at room temperature. (C) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2007.04.020