rac-2-azido-2-(para-nitro-phenyl)-ethanol | 325856-42-6

• 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: rac-2-azido-2-(para-nitro-phenyl)-ethanol
• 英文别名: (+/-)-2-azido-2-(4-nitrophenyl)ethanol；2-Azido-2-(para-nitrophenyl)ethanol；2-azido-2-(4-nitrophenyl)ethanol
• CAS: 325856-42-6
• 化学式: C₈H₈N₄O₃
• 分子量: 208.177
• InChiKey: ZEPXDCVIHLGTNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  80.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  rac-2-azido-2-(para-nitro-phenyl)-ethanol 、 4-叔丁基环己酮 在 三氟化硼乙醚 、 氢氧化钾 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以62%的产率得到5-tert-butyl-1-(2-hydroxy-1-(4-nitrophenyl)ethyl)azepan-2-one
  参考文献：
  名称：

  叠氮化物介导的不对称环膨胀反应中的非键，有吸引力的阳离子-π相互作用

  摘要：

  The influence of attractive, nonbonded interactions on the reactions of 1,2- and 1,3-hydroxyalkyl azides with ketones has been investigated through experimental and computational means. A series of 1,3-hydroxyalkyl azides bearing electronically tuned aromatic groups at the 2 position were prepared and reacted along with several derivatives designed to conformationally restrict the rotational orientation of the aromatic substituent. These studies showed that a cation-pi interaction between an aryl moiety and an N-2(+) leaving group plays a role in determining the stereoselectivity of these reactions. A series of ab initio calculations supported this hypothesis. A computational and experimental analysis suggested a primarily steric model for the analogous reactions of substituted 2-azido-1-ethanol analogues.

  DOI：

  10.1021/jo800222r
• 作为产物：
  描述：

  ω-bromo-para-nitro-acetophenone 在 sodium tetrahydroborate 、 sodium azide 作用下， 以 水 为溶剂， 反应 18.25h， 生成 rac-2-azido-2-(para-nitro-phenyl)-ethanol
  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

文献信息

• Some New Aspects of the Boyer Reaction
  作者：Rupak Chakraborty、Veronica Franz、Ghanashyam Bez、Dipali Vasadia、Chenchu Popuri、Cong-Gui Zhao

  DOI：10.1021/ol051442o

  日期：2005.9.1

  [reaction: see text] The reaction outcome of 2-azidoethanol and aliphatic aldehyde is found to be dependent on the catalyst and the structure of the azido alcohol. Under the catalysis of Cu(II) triflate, the corresponding acetal is obtained. A similar reaction between 2-aryl-2-azidoethanol and aldehyde catalyzed by BF3 yields a mixture of 3-oxazoline and 2-oxazoline. The latter reaction has been used

  [反应：见正文]发现2-叠氮基乙醇与脂肪醛的反应结果取决于叠氮基醇的催化剂和结构。在三氟甲磺酸铜（II）的催化下，获得了相应的缩醛。由BF 3催化的2-芳基-2-叠氮基乙醇与醛之间的类似反应产生了3-恶唑啉和2-恶唑啉的混合物。后一反应已用于制备具有良好对映选择性的3-恶唑啉。
• Enzymatic conversion of epoxides
  申请人：Rijksuniversiteit Groningen

  公开号：US20030124693A1

  公开（公告）日：2003-07-03

  The invention relates to a process for converting an epoxide to an alcohol. The process according to the invention is enzymatically catalyzed and highly enantioselective and regiospecific.

  本发明涉及一种将环氧化物转化为醇的方法。本发明的方法是通过酶催化反应实现的，具有高度对映选择性和区域特异性。
• ENZYMATIC CONVERSION OF EPOXIDES
  申请人：Lutje Spelberg Jeffrey Harald

  公开号：US20080220485A1

  公开（公告）日：2008-09-11

  The invention relates to a process for converting an epoxide to an alcohol. The process according to the invention is enzymatically catalyzed and highly enantioselective and regiospecific.

  本发明涉及一种将环氧化物转化为醇的方法。本发明的方法是通过酶催化的，具有高度的对映选择性和区域选择性。
• Azidolysis of epoxides catalysed by the halohydrin dehalogenase from Arthrobacter sp. AD2 and a mutant with enhanced enantioselectivity: an (S)-selective HHDH
  作者：Ana Mikleušević、Ines Primožič、Tomica Hrenar、Branka Salopek-Sondi、Lixia Tang、Maja Majerić Elenkov

  DOI：10.1016/j.tetasy.2016.08.003

  日期：2016.10

  Halohydrin dehalogenase from Arthrobacter sp. AD2 catalysed azidolysis of epoxides with high regioselectivity and low to moderate (S)-enantioselectivity (E = 1-16). Mutation of the asparagine 178 to alanine (N178A) showed increased enantioselectivity towards styrene oxide derivatives and glycidyl ethers. Conversion of aromatic epoxides was catalysed by HheA-N178A with complete enantioselectivity, however the regioselectivity was reduced. As a result of the enzyme-catalysed reaction, enantiomerically pure (S)-beta-azido alcohols and (R)-alpha-azido alcohols (ee >= 99%) were obtained. (C) 2016 Published by Elsevier Ltd.
• US7695942B2
  申请人：——

  公开号：US7695942B2

  公开（公告）日：2010-04-13