3-azido-1-(4-chlorophenyl)propanone | 950650-35-8

• 英文名称: 3-azido-1-(4-chlorophenyl)propanone
• 英文别名: 3-Azido-1-(4-chlorophenyl)propan-1-one
• CAS: 950650-35-8
• 化学式: C₉H₈ClN₃O
• 分子量: 209.635
• InChiKey: ZNPMYDNJNXEHAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-azido-1-(4-chlorophenyl)propanone 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 (RS)-3-azido-1-(4-chlorophenyl)propan-1-ol
  参考文献：
  名称：

  Synthesis of enantiomerically pure γ-azidoalcohols by lipase-catalyzed transesterification

  摘要：

  An enantioselective synthesis of chiral gamma-azidoalcohols via lipase-catalyzed resolution is described. The efficiency of various lipases and the effect of different solvents have been studied. Pseudomonas cepacia immobilized on diatomaceous earth (PS-D) in n-hexane catalyzed the transesterification process in an efficient manner providing gamma-azidoalcohols in high enantiomeric excess. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.03.028
• 作为产物：
  描述：

  3,4'-二氯苯丙酮 在 sodium azide 、 18-冠醚-6 作用下， 以 二氯甲烷 为溶剂， 生成 3-azido-1-(4-chlorophenyl)propanone
  参考文献：
  名称：

  Synthesis of enantiomerically pure γ-azidoalcohols by lipase-catalyzed transesterification

  摘要：

  An enantioselective synthesis of chiral gamma-azidoalcohols via lipase-catalyzed resolution is described. The efficiency of various lipases and the effect of different solvents have been studied. Pseudomonas cepacia immobilized on diatomaceous earth (PS-D) in n-hexane catalyzed the transesterification process in an efficient manner providing gamma-azidoalcohols in high enantiomeric excess. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.03.028

文献信息

• Regiocontrolled Wacker Oxidation of Cinnamyl Azides
  作者：Angela S. Carlson、Cristian Calcanas、Ryan M. Brunner、Joseph J. Topczewski

  DOI：10.1021/acs.orglett.8b00344

  日期：2018.3.16

  A highly regioselective Wacker oxidation has been developed for the oxidation of cinnamyl azides. The catalytic oxidation tolerates the azide functionality, and more than 15 β-azido ketones were isolated (25–92% yield). High regioselectivity for the aryl ketone is observed in all cases. A robustness screen was conducted to determine functional group tolerance. The products of the oxidaiton can be readily

  已经开发出对肉桂酰叠氮化物进行氧化的高度区域选择性的瓦克氧化。催化氧化可耐受叠氮化物的功能，并分离出15种以上的β-叠氮基酮（收率25-92％）。在所有情况下均观察到对芳基酮的高区域选择性。进行了健壮性筛选以确定官能团耐受性。氧化产物可以容易地多样化。
• Organocatalytic β-Azidation of Enones Initiated by an Electron-Donor–Acceptor Complex
  作者：Rajendra P. Shirke、S. S. V. Ramasastry

  DOI：10.1021/acs.orglett.7b02861

  日期：2017.10.6

  β-unsaturated ketones is described. Reaction of the Zhdankin azidoiodane with enones in the presence of a catalytic amount of an amine provides β-azido ketones via the formation of an electron-donor–acceptor complex. The application of this protocol is demonstrated through one-step elaborations leading to the synthesis of unprecedented classes of 1,2,3-triazoles.

  描述了一种操作简单的α，β-不饱和酮的有机催化β-叠氮化。Zhdankin叠氮碘烷与烯酮在催化量的胺存在下的反应通过电子给体-受体配合物的形成提供了β-叠氮基酮。该协议的应用通过一步一步精炼来证明，该合成导致合成前所未有的1,2,3-三唑类。