(1R)-2-氯-1-(4-硝基苯基)乙醇 | 325856-49-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (1R)-2-氯-1-(4-硝基苯基)乙醇
• 英文名称: (R)-2-chloro-1-(4-nitrophenyl)ethanol
• 英文别名: 2-chloro-1-(4'-nitrophenyl)ethanol；Benzenemethanol, alpha-(chloromethyl)-4-nitro-, (alphar)-；(1R)-2-chloro-1-(4-nitrophenyl)ethanol
• CAS: 325856-49-3
• 化学式: C₈H₈ClNO₃
• 分子量: 201.609
• InChiKey: ZUJVGRUIXVTXOX-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2906299090

反应信息

• 作为反应物：
  描述：

  (1R)-2-氯-1-(4-硝基苯基)乙醇 在 halohydrin dehalogenase from Agrobacterium radiobacter AD₁ 、 sodium chloride 作用下， 生成 (R)-2-(4-硝基苯基)环氧乙烷
  参考文献：
  名称：

  Highly Enantioselective and Regioselective Biocatalytic Azidolysis of Aromatic Epoxides

  摘要：

  [figure: see text] The halohydrin dehalogenase from Agrobacterium radiobacter AD1 catalyzed the highly enantioselective and beta-regioselective azidolysis of (substituted) styrene oxides. By means of kinetic resolutions the remaining epoxide and the formed azido alcohol could be obtained in very high ee. In a large scale conversion, the decrease in yield and selectivity due to the uncatalyzed chemical side reaction could be overcome by slow addition of azide.

  DOI：

  10.1021/ol0067540
• 作为产物：
  描述：

  2-氯-4'-硝基苯乙酮 在 potassium phosphate buffer 、 乙醇脱氢酶(NADP) 葡萄糖 、 D-glucose dehydrogenase 、 还原型辅酶II(NADPH)四钠盐 作用下， 以 水 为溶剂， 以76%的产率得到(1R)-2-氯-1-(4-硝基苯基)乙醇
  参考文献：
  名称：

  重要药物组成部分的“绿色”合成：酶法获得对映体纯的α-氯醇

  摘要：

  筛选了三十一种重组酮还原酶，以减少六种α-氯酮（药学上有价值的α-氯醇的前体）的还原。发现了几种高活性和对映选择性的酮还原酶，并以制备规模证明了它们在合成这些α-氯醇的两种对映异构体中的应用。这为此类重要的药物构建基块提供了便捷的“绿色”通道。

  DOI：

  10.1016/j.tetasy.2005.08.037

文献信息

• Highly enantioselective acylation of chlorohydrins using Amano AK lipase from P. fluorescens immobilized on silk fibroin–alginate spheres
  作者：Irlon M. Ferreira、Rodolfo H.V. Nishimura、Ana B. dos A. Souza、Giuliano C. Clososki、Sergio A. Yoshioka、André L.M. Porto

  DOI：10.1016/j.tetlet.2014.07.032

  日期：2014.9

  kinetic resolution mediated by Amano AK lipase from Pseudomonas fluorescens immobilized in silk friboin-alginate spheres. Thus, the enantioselectivity of the process was sufficient for the production of the desired alcohols and acetates in good yields and high enantiomeric purities. This Letter provides a simple, cheap, and practical protocol for enantioselective synthesis of chlorohydrins and reinforces

  选择含氯醇基团的芳族，烯丙基和脂族化合物作为底物，用于由固定在丝素-海藻酸盐球体中的荧光假单胞菌的Amano AK脂肪酶介导的酶促动力学拆分。因此，该方法的对映选择性足以以高收率和高对映体纯度生产所需的醇和乙酸酯。该信为氯醇的对映选择性合成提供了一种简单，廉价和实用的方案，并增强了丝素蛋白作为多相催化剂载体的多功能性。
• Tandem Concurrent Processes: One-Pot Single-Catalyst Biohydrogen Transfer for the Simultaneous Preparation of Enantiopure Secondary Alcohols
  作者：Fabricio R. Bisogno、Iván Lavandera、Wolfgang Kroutil、Vicente Gotor

  DOI：10.1021/jo802350f

  日期：2009.2.20

  A novel one-pot tandem biohydrogen transfer process to concurrently obtain two enantiopure sec-alcohols is presented; thus, using a suitable single enzyme and a catalytic amount of cofactor, several interesting building blocks could be easily achieved in an enantiocomplementary fashion, minimizing dramatically the quantity of reagents usually employed in the "coupled-substrate" approach.
• ‘Green’ synthesis of important pharmaceutical building blocks: enzymatic access to enantiomerically pure α-chloroalcohols
  作者：Dunming Zhu、Chandrani Mukherjee、Ling Hua

  DOI：10.1016/j.tetasy.2005.08.037

  日期：2005.10

  α-chloroketones, the precursors of pharmaceutically valuable α-chloroalcohols. Several highly active and enantioselective ketoreductases were found and their applications to the synthesis of both enantiomers of these α-chloroalcohols were demonstrated on a preparative scale. This offers a convenient, ‘green’ access to this type of important pharmaceutical building blocks.

  筛选了三十一种重组酮还原酶，以减少六种α-氯酮（药学上有价值的α-氯醇的前体）的还原。发现了几种高活性和对映选择性的酮还原酶，并以制备规模证明了它们在合成这些α-氯醇的两种对映异构体中的应用。这为此类重要的药物构建基块提供了便捷的“绿色”通道。
• Highly Enantioselective and Regioselective Biocatalytic Azidolysis of Aromatic Epoxides
  作者：Jeffrey H. Lutje Spelberg、Johan E. T. van Hylckama Vlieg、Lixia Tang、Dick B. Janssen、Richard M. Kellogg

  DOI：10.1021/ol0067540

  日期：2001.1.1

  [figure: see text] The halohydrin dehalogenase from Agrobacterium radiobacter AD1 catalyzed the highly enantioselective and beta-regioselective azidolysis of (substituted) styrene oxides. By means of kinetic resolutions the remaining epoxide and the formed azido alcohol could be obtained in very high ee. In a large scale conversion, the decrease in yield and selectivity due to the uncatalyzed chemical side reaction could be overcome by slow addition of azide.