(S)-1-phenylethyl azide | 31002-29-6

• 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: (S)-1-phenylethyl azide
• 英文别名: [(1S)-1-azidoethyl]benzene
• CAS: 31002-29-6
• 化学式: C₈H₉N₃
• 分子量: 147.18
• InChiKey: KOFFFKMEMKRWMT-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  11
• 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：
  14.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-1-phenylethyl azide 在 zinc(II) tetrahydroborate 、 silica gel 作用下， 以 乙二醇二甲醚 为溶剂， 反应 8.0h， 以62%的产率得到(S)-(-)- α-甲基苄胺
  参考文献：
  名称：

  Reduction of Azides with Zinc Borohydride

  摘要：

  Zinc borohydride in 1,2-dimethoxyethane provides an efficient procedure for the reduction of organic azides. Aroyl, acyl, and arylsulfonyl azides readily undergo reduction at room temperature to produce amides and sulfonamides in excellent yields; however, substitution with electron-withdrawing groups in the aroyl azides leads to the corresponding benzyl alcohols. Reduction of aryl and alkyl azides has also been achieved in high yields, under some modified conditions.

  DOI：

  10.1021/jo00094a021
• 作为产物：
  描述：

  (R)-(+)-1-苯基乙醇 在 二(对硝基苯基)叠氮膦酸酯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以94%的产率得到(S)-1-phenylethyl azide
  参考文献：
  名称：

  Efficient method for the one-pot azidation of alcohols using bis(p-nitrophenyl) phosphorazidate

  摘要：

  使用双（对硝基苯基）磷酸酰肼和DBU，可以高效地将各种醇和己糖吡喃转化为相应的烷基叠氮化物和糖苷叠氮化物。

  DOI：

  10.1039/a705768g

文献信息

• [EN] METHOD OF CONVERTING ALCOHOL TO HALIDE<br/>[FR] PROCÉDÉ DE CONVERSION D'UN ALCOOL EN HALOGÉNURE
  申请人：UNIV SAARLAND

  公开号：WO2016202894A1

  公开（公告）日：2016-12-22

  The present invention relates to a method of converting an alcohol into a corresponding halide. This method comprises reacting the alcohol with an optionally substituted aromatic carboxylic acid halide in presence of an N-substituted formamide to replace a hydroxyl group of the alcohol by a halogen atom. The present invention also relates to a method of converting an alcohol into a corresponding substitution product. The second method comprises: (a) performing the method of the invention of converting an alcohol into the corresponding halide; and (b) reacting the corresponding halide with a nucleophile to convert the halide into the nucleophilic substitution product.

  本发明涉及一种将醇转化为相应卤化物的方法。该方法包括在N-取代甲酰胺的存在下，将醇与可选择取代的芳香羧酸卤化物反应，以通过卤原子取代醇的羟基。本发明还涉及一种将醇转化为相应取代产物的方法。第二种方法包括：(a)执行将醇转化为相应卤化物的本发明方法；以及(b)将相应卤化物与亲核试剂反应，将卤化物转化为亲核取代产物。
• Iron-Catalyzed Asymmetric Decarboxylative Azidation
  作者：Kaikai Wang、Yajun Li、Xiaoyan Li、Daliang Li、Hongli Bao

  DOI：10.1021/acs.orglett.1c03355

  日期：2021.11.19

  The first iron-catalyzed asymmetric azidation of benzylic peresters has been reported with trimethylsilyl azide (TMSN3) as the azido source. Hydrocarbon radicals that lack of strong interactions were capable to be enantioselectively azidated. The reaction features good functional group tolerance, high yields, and mild conditions. The chiral benzylic azides can further be used in click reaction, phosphoramidation

  已经报道了以三甲基甲硅烷基叠氮化物 (TMSN 3 ) 作为叠氮源的第一次铁催化的苄基过酸酯的不对称叠氮化。缺乏强相互作用的烃基能够被对映选择性叠氮化。该反应具有官能团耐受性好、产率高、条件温和等特点。手性苄基叠氮化物可进一步用于点击反应、磷酰胺化和还原胺化，这证明了该反应的合成价值。
• Process for the preparation of azide derivatives
  申请人：Eisai Co., Ltd.

  公开号：US05986088A1

  公开（公告）日：1999-11-16

  A process for the preparation of azide derivatives useful as drugs, perfumes or intermediates of dyes by reacting an alcohol derivative with di-p-nitrophenyl phosphorazidate in the presence of 1,8-diazabicyclo[5.4.0]-7-undecene.

  一种制备偶氮衍生物的方法，可用作药物、香料或染料中间体，通过在1,8-二氮杂双环[5.4.0]-7-十一烯存在下，将醇衍生物与二对硝基苯磷酰叠氮酸酯反应。
• Gold Sulfinyl Mesoionic Carbenes: Synthesis, Structure, and Catalytic Activity
  作者：María Frutos、Marta G. Avello、Alma Viso、Roberto Fernández de la Pradilla、María C. de la Torre、Miguel A. Sierra、Heinz Gornitzka、Catherine Hemmert

  DOI：10.1021/acs.orglett.6b01555

  日期：2016.8.5

  the five membered ring have been prepared and tested as catalysts in the cycloisomerization of enynes. These new catalysts are very efficient, with the sulfoxide moiety playing a key role in their activity and the N1-substituent in control of the regioselectivity of these processes.

  已经制备了具有连接在五元环的C 4位上的手性亚砜基的金中离子卡宾，并在烯炔的环异构化中作为催化剂进行了测试。这些新催化剂非常有效，亚砜部分在其活性中起着关键作用，而N 1-取代基在控制这些过程的区域选择性中起着关键作用。
• Sulfonyl‐PYBOX Ligands Enable Kinetic Resolution of α‐Tertiary Azides by CuAAC
  作者：Yi Gong、Cai Wang、Feng Zhou、Kui Liao、Xi‐Yu Wang、Ying Sun、Yan‐Xue Zhang、Zhi Tu、Xin Wang、Jian Zhou

  DOI：10.1002/anie.202301470

  日期：——

  We report the first highly selective kinetic resolution of racemic α-chiral azides by Cu-catalyzed azide-alkyne cycloadditions (CuAAC), providing facile access to chiral α-tertiary azides and 1,2,3-triazoles with newly developed PYBOX ligands with a C4 sulfonyl group. The key role of the C4 sulfonyl in tuning the electronic and steric properties of the chiral catalysts to enhance enantiomer discrimination

  我们报告了通过 Cu 催化的叠氮化物-炔烃环加成 (CuAAC) 对外消旋 α-手性叠氮化物的首次高选择性动力学拆分，提供了通过新开发的 PYBOX 配体轻松获得手性 α-叔叠氮化物和 1,2,3-三唑C4磺酰基。DFT 计算合理化了 C4 磺酰基在调节手性催化剂的电子和空间特性以增强对映异构体区分方面的关键作用。