(2S)-1-(2-cyanophenoxy)-2,3-propanediol | 56715-37-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2S)-1-(2-cyanophenoxy)-2,3-propanediol
• 英文别名: (S)-3-(2-cyanophenoxy)-propane-1,2-diol；(S)-3-(2-cyanophenoxy)propane-1,2-diol；2-[(2S)-2,3-dihydroxypropoxy]benzonitrile
• CAS: 56715-37-8
• 化学式: C₁₀H₁₁NO₃
• 分子量: 193.202
• InChiKey: GFPFQGFERWRLRO-VIFPVBQESA-N

物化性质

• 沸点：
  425.6±30.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  73.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S)-1-(2-cyanophenoxy)-2,3-propanediol 在 ruthenium trichloride 、 sodium periodate 、 氯化亚砜 、 三乙胺 、 lithium bromide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 5.0h， 生成 (S)-(+)-3-(2-cyanophenoxy)-1,2-epoxypropane
  参考文献：
  名称：

  通过OsO 4催化的不对称二羟基化反应不对称合成芳氧基丙醇胺

  摘要：

  描述了一种简单有效的方法，该方法包括对映异构体合成首个不对称合成西酞洛尔的β-肾上腺素能阻断剂。关键步骤是（i）芳基烯丙基醚无尖锐的不对称二羟基化反应，以将手性引入分子中；以及（ii）使用三步法将环状硫酸盐转化为相应的环氧化物。

  DOI：

  10.1016/j.tet.2005.01.074
• 作为产物：
  描述：

  邻羟基苯甲腈 、 (S)-3-氯-1,2-丙二醇 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以65%的产率得到(2S)-1-(2-cyanophenoxy)-2,3-propanediol
  参考文献：
  名称：

  Spontaneous resolution amongst chiral ortho-cyanophenyl glycerol derivatives: an effective preferential crystallization approach to a single enantiomer of the β-adrenoblocker bunitrolol

  摘要：

  The beta-adrenoblocker bunitrolol 1 as well as intermediate cyclic sulfate 6 and glycidyl ether 8 have been prepared in enantiopure form by starting from enantiopure o-cyanophenyl glycerol ether 2 by an entrainment resolution procedure. Thermal investigations reveal that 1 center dot HCl forms a moderately stable racemic compound, whereas 2, 6 and 8 are conglomerate forming substances potentially capable of entrainment resolution. Some chemical and chiroptical characteristics for bunitrolol and possible intermediates in its synthesis were Corrected, and configurations were verified with the configuration of 1 center dot HCl. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.05.025

文献信息

• Chiral lariat ethers based on spontaneously resolved 3-(2-cyanophenoxy)propane-1,2-diol
  作者：R. R. Fayzullin、Z. A. Bredikhina、D. R. Sharafutdinova、O. B. Bazanova、A. A. Bredikhin

  DOI：10.1134/s1070428014040319

  日期：2014.4
• Asymmetric synthesis of aryloxypropanolamines via OsO4-catalyzed asymmetric dihydroxylation
  作者：Iliyas A. Sayyed、Vinay V. Thakur、Milind D. Nikalje、Gajanan K. Dewkar、S.P. Kotkar、A. Sudalai

  DOI：10.1016/j.tet.2005.01.074

  日期：2005.3

  effective procedure for the enantioselective synthesis of several β-adrenergic blocking agents incorporating the first asymmetric synthesis of celiprolol, is described. The key steps are (i) sharpless asymmetric dihydroxylation of aryl allyl ethers to introduce chirality into the molecules and (ii) conversion of cyclic sulfates into the corresponding epoxides using a three-step procedure.

  描述了一种简单有效的方法，该方法包括对映异构体合成首个不对称合成西酞洛尔的β-肾上腺素能阻断剂。关键步骤是（i）芳基烯丙基醚无尖锐的不对称二羟基化反应，以将手性引入分子中；以及（ii）使用三步法将环状硫酸盐转化为相应的环氧化物。
• Spontaneous resolution amongst chiral ortho-cyanophenyl glycerol derivatives: an effective preferential crystallization approach to a single enantiomer of the β-adrenoblocker bunitrolol
  作者：Zemfira A. Bredikhina、Flyura S. Akhatova、Dmitry V. Zakharychev、Alexander A. Bredikhin

  DOI：10.1016/j.tetasy.2008.05.025

  日期：2008.6

  The beta-adrenoblocker bunitrolol 1 as well as intermediate cyclic sulfate 6 and glycidyl ether 8 have been prepared in enantiopure form by starting from enantiopure o-cyanophenyl glycerol ether 2 by an entrainment resolution procedure. Thermal investigations reveal that 1 center dot HCl forms a moderately stable racemic compound, whereas 2, 6 and 8 are conglomerate forming substances potentially capable of entrainment resolution. Some chemical and chiroptical characteristics for bunitrolol and possible intermediates in its synthesis were Corrected, and configurations were verified with the configuration of 1 center dot HCl. (C) 2008 Elsevier Ltd. All rights reserved.