(S)-1-chloro-3-(phenylseleno)-propan-2-ol | 918443-05-7

• 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-chloro-3-(phenylseleno)-propan-2-ol
• 英文别名: (S)-1-chloro-3-(phenylselanyl)propan-2-ol；(2S)-1-Chloro-3-(phenylselanyl)propan-2-ol；(2S)-1-chloro-3-phenylselanylpropan-2-ol
• CAS: 918443-05-7
• 化学式: C₉H₁₁ClOSe
• 分子量: 249.599
• InChiKey: ZZXVKDQQTIQBQF-QMMMGPOBSA-N

物化性质

• 沸点：
  336.0±42.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.03
• 重原子数：
  12
• 可旋转键数：
  4
• 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：

  (2Z)-2-[[5-(3,4-二甲基-5-硝基苯基)-2-呋喃基]亚甲基]-7-甲基-3-氧代-5-苯基-5H-噻唑并[3,2-a]嘧啶-6-羧酸乙酯 在 PS-C II Amano lipase 、 β-环糊精 作用下， 以 甲苯 为溶剂， 反应 0.5h， 生成 (S)-1-chloro-3-(phenylseleno)-propan-2-ol
  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

• Ultrasound Assisted Ring-Opening Reaction of Epoxides with 1,2-DiphenylDiselenide
  作者：Tianxing Cheng、Xiangyong Zheng、Qiang Ke

  DOI：10.3184/174751911x13149579868111

  日期：2011.9

  Ultrasound assisted ring-opening of epoxides with 1,2-diphenyldiselenide in PEG-400/H₂O in the presence of sodium dithionite has been developed, affording β-hydroxy selenides with high regioselectivity in good to excellent yields. Importantly, the present protocol is very practical and highly efficient since it does not require the use of expensive and unpleasant smelly reagent.

  在 PEG-400/H2O 中，在亚硫酸氢钠的存在下，开发了超声波辅助环氧化物与 1,2-二苯基二硒化物的开环反应，以良好甚至极佳的产率获得了具有高区域选择性的 β-羟基硒化物。重要的是，本方案无需使用昂贵且气味难闻的试剂，因此非常实用且高效。
• Lv, Guangshu; Li, Ting; Hu, Ruijia, Journal of Chemical Research, 2010, # 10, p. 549 - 552
  作者：Lv, Guangshu、Li, Ting、Hu, Ruijia、Chen, Jiuxi、Ding, Jinchang、Wu, Huayue

  DOI：——

  日期：——
• 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.