2-azido-1-(4-cyanophenyl)-ethanol | 1255944-52-5

• 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: 2-azido-1-(4-cyanophenyl)-ethanol
• 英文别名: 4-(2-Azido-1-hydroxyethyl)benzonitrile
• CAS: 1255944-52-5
• 化学式: C₉H₈N₄O
• 分子量: 188.189
• InChiKey: UBGUGERXSLLBEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  58.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-azido-1-(4-cyanophenyl)-ethanol 、 乙酸酐 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 2-azido-1-(4'-cyanophenyl)ethyl acetate
  参考文献：
  名称：

  1,2-叠氮基醇酯催化转化为[小α]-酰胺基酮

  摘要：

  1,2-叠氮基醇的酯通过Ru催化形成的NH亚胺与N 2的释放而随后在分子内的迁移而转化为无外部氧化剂的小α-酰胺基酮。

  DOI：

  10.1039/c6cc02063a
• 作为产物：
  描述：

  2-溴-4'-氰基苯乙酮 在 sodium tetrahydroborate 、 sodium azide 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 1.17h， 生成 2-azido-1-(4-cyanophenyl)-ethanol
  参考文献：
  名称：

  1,2-叠氮基醇酯催化转化为[小α]-酰胺基酮

  摘要：

  1,2-叠氮基醇的酯通过Ru催化形成的NH亚胺与N 2的释放而随后在分子内的迁移而转化为无外部氧化剂的小α-酰胺基酮。

  DOI：

  10.1039/c6cc02063a

文献信息

• Combining Designer Cells and Click Chemistry for a One-Pot Four-Step Preparation of Enantiopure β-Hydroxytriazoles
  作者：Wiktor Szymanski、Christiaan P. Postema、Chiara Tarabiono、Florian Berthiol、Lachlan Campbell-Verduyn、Stefaan de Wildeman、Johannes G. de Vries、Ben L. Feringa、Dick B. Janssen

  DOI：10.1002/adsc.201000502

  日期：2010.9.10

  The multistep catalytic process using designer cells, either added as freshly prepared suspensions or as stable lyophilized powder, and click reaction can be performed in one pot. The sequence of four reactions allows the production of both enantiomers of β‐hydroxytriazoles with high enantiomeric excess.

  使用设计器细胞的多步催化过程，既可以作为新鲜制备的悬浮液添加，也可以作为稳定的冻干粉末添加，然后单击反应可以在一锅中进行。四个反应的顺序允许生产具有高对映体过量的β-羟基三唑的两种对映体。
• 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.
• Non-enzymatic kinetic resolution of 1,2-azidoalcohols using a planar-chiral DMAP derivative catalyst
  作者：Laura Mesas-Sánchez、Alba E. Díaz-Álvarez、Peter Dinér

  DOI：10.1016/j.tet.2012.10.077

  日期：2013.1

  Optically pure 1,2-azidoalcohols are widely used as precursors for other high value organic products. A non-enzymatic kinetic resolution procedure for the stereoselective synthesis of chiral 1,2-azidoalcohols from the readily available racemic counterparts has been developed, employing a planar-chiral DMAP derivative catalyst. Following this procedure, a range of aromatic 1,2-azidoalcohols was obtained in good selectivities (up to S=45) and high enantiomeric excess (up to 99% ee). (c) 2012 Elsevier Ltd. All rights reserved.