(S)-2-benzyl-5-(4-pentylphenyl)-3-phenyl-2,3-dihydroisoxazole | 1144045-69-1

• 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: (S)-2-benzyl-5-(4-pentylphenyl)-3-phenyl-2,3-dihydroisoxazole
• 英文别名: (3S)-2-benzyl-5-(4-pentylphenyl)-3-phenyl-3H-1,2-oxazole
• CAS: 1144045-69-1
• 化学式: C₂₇H₂₉NO
• 分子量: 383.533
• InChiKey: SMPFCHNCRCPGJX-SANMLTNESA-N

物化性质

• 沸点：
  526.6±60.0 °C(predicted)
• 密度：
  1.092±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-Benzylidenebenzylamine N-oxide 、 4-戊基苯乙炔 在 N-benzyl-N-[1-(4-methoxyphenyl)-3-phenylprop-2-ynyl]hydroxylamine 、 Dimethylzinc 、 (+)-二叔丁基 L-酒石酸 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 90.0h， 以42%的产率得到(S)-2-benzyl-5-(4-pentylphenyl)-3-phenyl-2,3-dihydroisoxazole
  参考文献：
  名称：

  One Pot Synthesis of Optically Active 4-Isoxazolines by Asymmetric Addition of Alkynylzinc Reagents to Nitrones Followed by Cyclization

  摘要：

  One pot synthesis of optically active 4-isoxazolines was achieved by asymmetric addition of alkynylzinc reagents to nitrones utilizing di(t-butyl) (R,R)-tartrate as a chiral auxiliary followed by cyclization. By addition of dimethylzinc, the cyclization step was accelerated to afford the corresponding 4-isoxazolines with up to 93% ee. Furthermore, a cyclized zinc intermediate could be trapped with formaldehyde to give the corresponding 2,3,4,5-tetrasubstituted 4-isoxazoline with 85% ee.

  DOI：

  10.3987/com-08-11566

文献信息

• One Pot Synthesis of Optically Active 4-Isoxazolines by Asymmetric Addition of Alkynylzinc Reagents to Nitrones Followed by Cyclization
  作者：Yutaka Ukaji、Katsuhiko Inomata、Weilin Wei、Masato Kobayashi

  DOI：10.3987/com-08-11566

  日期：——

  One pot synthesis of optically active 4-isoxazolines was achieved by asymmetric addition of alkynylzinc reagents to nitrones utilizing di(t-butyl) (R,R)-tartrate as a chiral auxiliary followed by cyclization. By addition of dimethylzinc, the cyclization step was accelerated to afford the corresponding 4-isoxazolines with up to 93% ee. Furthermore, a cyclized zinc intermediate could be trapped with formaldehyde to give the corresponding 2,3,4,5-tetrasubstituted 4-isoxazoline with 85% ee.