[3-(4-Chlorophenoxy)-2-hydroxypropyl] nitrate | 217322-53-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: [3-(4-Chlorophenoxy)-2-hydroxypropyl] nitrate
• CAS: 217322-53-7
• 化学式: C₉H₁₀ClNO₅
• 分子量: 247.635
• InChiKey: FVSIXZOZPZYOHX-UHFFFAOYSA-N

物化性质

• 沸点：
  343.3±32.0 °C(Predicted)
• 密度：
  1.411±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  84.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  乙酸乙烯酯 、 [3-(4-Chlorophenoxy)-2-hydroxypropyl] nitrate 在 lipase from Pseudomonas cepacia Amano PS 作用下， 以 正己烷 为溶剂， 反应 80.0h， 生成 、 、 [(2R)-3-(4-chlorophenoxy)-2-hydroxypropyl] nitrate 、 [(2S)-1-(4-chlorophenoxy)-3-nitrooxypropan-2-yl] acetate
  参考文献：
  名称：

  Resolution of racemic 3-aryloxy-1-nitrooxypropan-2-ols by lipase-catalyzed enantioselective acetylation

  摘要：

  Both (R)- and (S)-enantiomers of 3-aryloxy-1-nitrooxypropan-2-ols (R)-(-)-1, (S)-(+)-2 were prepared in high enantiomeric excess by lipase from Pseudomonas cepacia (Amano PS) or Pseudomonas fluorescens (Amano AK)-catalyzed acetylation of racemic alcohols la-g with vinyl acetate in n-hexane at 4 or 22 degreesC. The enantio selectivity of this transformation was dependent on the substitution pattern of the aryl ring with E-values ranging from 31 to 111. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00378-0
• 作为产物：
  描述：

  4-氯苯基缩水甘油醚 在 bismuth(III) nitrate 作用下， 以 乙腈 为溶剂， 反应 1.5h， 以91%的产率得到[3-(4-Chlorophenoxy)-2-hydroxypropyl] nitrate
  参考文献：
  名称：

  使用硝酸铋将环氧乙烷和氮丙啶高效地和立体选择性转化为β-（硝基氧基）取代的醇和胺†

  摘要：

  环氧乙烷和氮丙啶在室温下通过硝酸铋有效地开环，分别提供相应的β-（硝基氧基）取代的醇和胺。所述转化是高度区域选择性和立体选择性的，并且在短时间内以优异的产率提供了硝基氧基化合物。

  DOI：

  10.1002/hlca.200790002

文献信息

• Lipase-Catalyzed Kinetic Resolution of the Racemic Mixtures of 1-Aryloxy-3-Nitrato-and 1-Aryloxy-3-Azido-2-Propanols
  作者：Beata Pchelka、Justyna Radomska、Jan Plenkiewicz

  DOI：10.1080/00397919808004470

  日期：1998.12

  Abstract The racemic mixtures of 1-aryloxy-3-nitrato-2-propanols and 1-aryloxy-3-azido-2-propanols were resolved with moderate selectivity by the lipase-mediated acylation with vinyl acetate. The effects of the nature, position, and spatial requirements of the phenyl-ring substituents on the resolution degree were investigated.

  摘要 1-芳氧基-3-硝基-2-丙醇和1-芳氧基-3-叠氮基-2-丙醇的外消旋混合物通过脂肪酶介导的乙酸乙烯酯酰化以中等选择性拆分。研究了苯环取代基的性质、位置和空间要求对分辨率的影响。
• Zirconyl nitrate mediated regioselective ring opening of epoxides and aziridines: an easy synthesis of β-nitrato-alcohols and -sulfonamides
  作者：Biswanath Das、Maddeboina Krishnaiah、Katta Venkateswarlu

  DOI：10.1016/j.tetlet.2006.06.114

  日期：2006.8

  Epoxides and aziridines are cleaved efficiently and regioselectively in the presence of zirconyl nitrate at room temperature to afford the corresponding beta-nitrato-alcohols and -sulfonamides, respectively, in high yields. (c) 2006 Elsevier Ltd. All rights reserved.
• Efficient Regio- and Stereoselective Conversions of Oxiranes and Aziridines intoβ-(Nitrooxy)-Substituted Alcohols and Amines by Using Bismuth Nitrate
  作者：Biswanath Das、Maddeboina Krishnaiah、Katta Venkateswarlu、Vtukuri Saidi Reddy

  DOI：10.1002/hlca.200790002

  日期：2007.1

  Oxiranes and aziridines efficiently undergo ring opening with bismuth nitrate at room temperature to furnish the corresponding β-(nitrooxy)-substituted alcohols and amines respectively. The conversions are highly regio- and stereoselective and afford the nitrooxy-compounds in excellent yields within a short period of time.

  环氧乙烷和氮丙啶在室温下通过硝酸铋有效地开环，分别提供相应的β-（硝基氧基）取代的醇和胺。所述转化是高度区域选择性和立体选择性的，并且在短时间内以优异的产率提供了硝基氧基化合物。
• Resolution of racemic 3-aryloxy-1-nitrooxypropan-2-ols by lipase-catalyzed enantioselective acetylation
  作者：Beata Krystyna Pchelka、André Loupy、Jan Plenkiewicz、Alain Petit、Luis Blanco

  DOI：10.1016/s0957-4166(01)00378-0

  日期：2001.8

  Both (R)- and (S)-enantiomers of 3-aryloxy-1-nitrooxypropan-2-ols (R)-(-)-1, (S)-(+)-2 were prepared in high enantiomeric excess by lipase from Pseudomonas cepacia (Amano PS) or Pseudomonas fluorescens (Amano AK)-catalyzed acetylation of racemic alcohols la-g with vinyl acetate in n-hexane at 4 or 22 degreesC. The enantio selectivity of this transformation was dependent on the substitution pattern of the aryl ring with E-values ranging from 31 to 111. (C) 2001 Elsevier Science Ltd. All rights reserved.