(S)-1-(phenylseleno)-hex-5-en-2-ol | 918443-04-6

• 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)-1-(phenylseleno)-hex-5-en-2-ol
• 英文别名: (2S)-1-(Phenylselanyl)hex-5-EN-2-OL；(2S)-1-phenylselanylhex-5-en-2-ol
• CAS: 918443-04-6
• 化学式: C₁₂H₁₆OSe
• 分子量: 255.218
• InChiKey: LYKLQCLSUFUMCS-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.76
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  乙酸乙烯酯 、 (+/-)-1-(phenylseleno)-hex-5-en-2-ol 在 PS-C II Amano lipase 作用下， 以 甲苯 为溶剂， 反应 25.0h， 生成 (R)-1-(phenylseleno)-hex-5-en-2-ol 、 (S)-1-(phenylseleno)-hex-5-en-2-ol 、 (S)-1-(phenylseleno)-hex-5-en-2-yl acetate 、 (R)-1-(phenylseleno)-hex-5-en-2-yl acetate
  参考文献：
  名称：

  Lipase-catalyzed resolution of β-hydroxy selenides

  摘要：

  Eleven beta-hydroxy selenides were kinetically resolved using an immobilized lipase (Amano PS-C II) in toluene in the presence of vinyl acetate at 30 degrees C. This approach provided, in several cases, both enantiomers in high enantiomeric excess. The role of the size of substituents and the behaviour of cyclic beta-hydroxy selenides is also discussed. Enantiopure beta-hydroxy selenides are useful building blocks. As an application of this chemistry, enantiopure (1S,2R)-indene oxide was obtained in one step from the proper enantiopure beta-hydroxy selenide. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2006.10.010

文献信息

• Lipase-catalyzed resolution of β-hydroxy selenides
  作者：Michelangelo Gruttadauria、Paolo Lo Meo、Serena Riela、Francesca D’Anna、Renato Noto

  DOI：10.1016/j.tetasy.2006.10.010

  日期：2006.10

  Eleven beta-hydroxy selenides were kinetically resolved using an immobilized lipase (Amano PS-C II) in toluene in the presence of vinyl acetate at 30 degrees C. This approach provided, in several cases, both enantiomers in high enantiomeric excess. The role of the size of substituents and the behaviour of cyclic beta-hydroxy selenides is also discussed. Enantiopure beta-hydroxy selenides are useful building blocks. As an application of this chemistry, enantiopure (1S,2R)-indene oxide was obtained in one step from the proper enantiopure beta-hydroxy selenide. (c) 2006 Published by Elsevier Ltd.