phenyl azide-D5 | 85770-99-6

• 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: phenyl azide-D5
• 英文别名: 1-Azido-2,3,4,5,6-pentadeuteriobenzene；1-azido-2,3,4,5,6-pentadeuteriobenzene
• CAS: 85770-99-6
• 化学式: C₆H₅N₃
• 分子量: 124.086
• InChiKey: CTRLRINCMYICJO-RALIUCGRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  phenyl azide-D5 、 苯乙炔-D5 在 copper(ll) sulfate pentahydrate 、 重水 、 sodium ascorbate 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以72%的产率得到5-deutero-1,4-diphenyl-D₁₀-1H-1,2,3-triazole
  参考文献：
  名称：

  Synthesis of Deuterated 1,2,3-Triazoles

  摘要：

  The copper-catalyzed azide alkyne cycloaddition (CuAAC) is a highly effective method for the selective incorporation of deuterium atom into the C-5 position of the 1,2,3-triazole structure. Reactions of alkynes and azides can be conveniently carried out in a biphasic medium of CH2Cl2/D2O, using the CuSO4/Na ascorbate system. The mildness of the method renders it applicable to substrates of relatively high complexity, such as nucleosides. Good yields and high levels of deuterium incorporation were observed. A reaction conducted in equimolar H2O and D2O showed 2.7 times greater incorporation of hydrogen atom as compared to deuterium. This is consistent with the H+ and D+ ion concentrations in H2O and D2O, respectively. With appropriately deuterated precursors, partially to fully deuterated triazoles were assembled where the final deuterium atom was incorporated in the triazole-forming step.

  DOI：

  10.1021/jo301146j
• 作为产物：
  描述：

  苯胺-2,3,4,5,6-d5 在 亚硝酸特丁酯 、 叠氮基三甲基硅烷 作用下， 以 乙腈 为溶剂， 60.0 ℃ 、689.49 kPa 条件下， 反应 0.83h， 生成 phenyl azide-D5
  参考文献：
  名称：

  使用新型整体式三苯基膦试剂进行有机叠氮化物的流式合成以及亚胺和胺的多步合成†

  摘要：

  在这里，我们描述了合成烷基和芳基叠氮化物的一般流程，以及新的整体式三苯基膦试剂的开发，这为在流动中使用这种多功能试剂提供了便利的形式。这些新工具的实用性已通过将其应用到Staudinger aza-Wittig流式反应序列中得到证明。最后，设计了多步的aza-Wittig，还原和纯化流程，允许以自动化方式访问胺产品。

  DOI：

  10.1039/c0ob00813c

文献信息

• Flow synthesis of organic azides and the multistep synthesis of imines and amines using a new monolithic triphenylphosphine reagent
  作者：Catherine J. Smith、Christopher D. Smith、Nikzad Nikbin、Steven V. Ley、Ian R. Baxendale

  DOI：10.1039/c0ob00813c

  日期：——

  Here we describe general flow processes for the synthesis of alkyl and aryl azides, and the development of a new monolithic triphenylphosphine reagent, which provides a convenient format for the use of this versatile reagent in flow. The utility of these new tools was demonstrated by their application to a flow Staudinger aza-Wittig reaction sequence. Finally, a multistep aza-Wittig, reduction and

  在这里，我们描述了合成烷基和芳基叠氮化物的一般流程，以及新的整体式三苯基膦试剂的开发，这为在流动中使用这种多功能试剂提供了便利的形式。这些新工具的实用性已通过将其应用到Staudinger aza-Wittig流式反应序列中得到证明。最后，设计了多步的aza-Wittig，还原和纯化流程，允许以自动化方式访问胺产品。
• Vibrational Spectroscopy and Analysis of Pseudo-tetrahedral Complexes with Metal Imido Bonds
  作者：Mark P. Mehn、Steven D. Brown、David M. Jenkins、Jonas C. Peters、Lawrence Que

  DOI：10.1021/ic060670r

  日期：2006.9.1

  which the added electron resides in a relatively nonbonding orbital. Replacement of the tBu group with a phenyl ring leads to a significantly more complicated resonance Raman spectrum, presumably due to coupling with the vibrations of the phenyl ring. Polarization studies demonstrate that the observed modes have A(1) symmetry. In this case, a clearer resonance enhancement of the signals is observed

  先前已经针对金属氮拉伸（nu（M-NR）），NR拉伸（nu（MN-R））以及与末端结合的酰亚胺相关的可能的配体变形模式提出了许多要求。在这里，我们研究了单阴离子三齿配体[PhBP3]（[PhBP3] = [PhB（CH2PPh2）3]-）的单核铁（III）和钴（III）亚胺配合物，以阐明这些三价金属酰亚胺的振动特征。我们报告[PhBP3] FeNtBu和[PhBP3] CoNtBu的结构。这些类型的伪四面体金属酰亚胺表现出较短的键长（约1.65 A）和围绕MNC键的近似线性角度，表明具有多重键特征。此外，这些化合物引起强烈的，低能量的可见吸收。[PhBP3] MNR络合物中光学带的位置和强度均取决于取代基是烷基还是芳基。激发[PhBP3] FeNtBu的低能带会在1104和1233 cm（-1）处产生两个拉曼特征，这两个特征都对15N和2H标记敏感。同位素标记表明1104 cm（-1）模式具有最大的Fe-N拉伸特性，而1233
• METHODS FOR PREPARING DEUTERATED 1,2,3-TRIAZOLES
  申请人：Lakshman Mahesh K.

  公开号：US20140107327A1

  公开（公告）日：2014-04-17

  This disclosure relates to a method that involves reacting an azide with an alkyne in the presence of deuterated water and a copper-containing catalyst, thereby forming a deuterated 1,2,3-triazole.

  本公开涉及一种方法，其中在氘代水和含铜催化剂的存在下，将偶氮与炔反应，从而形成氘代的1,2,3-三唑。
• [EN] METHODS FOR PREPARING DEUTERATED 1,2,3-TRIAZOLES<br/>[FR] PROCÉDÉS DE PRÉPARATION DE 1,2,3-TRIAZOLES DEUTÉRIÉS
  申请人：UNIV CITY NEW YORK RES FOUND

  公开号：WO2012135112A3

  公开（公告）日：2012-11-22
• Synthesis of Deuterated 1,2,3-Triazoles
  作者：Hari K. Akula、Mahesh K. Lakshman

  DOI：10.1021/jo301146j

  日期：2012.10.19

  The copper-catalyzed azide alkyne cycloaddition (CuAAC) is a highly effective method for the selective incorporation of deuterium atom into the C-5 position of the 1,2,3-triazole structure. Reactions of alkynes and azides can be conveniently carried out in a biphasic medium of CH2Cl2/D2O, using the CuSO4/Na ascorbate system. The mildness of the method renders it applicable to substrates of relatively high complexity, such as nucleosides. Good yields and high levels of deuterium incorporation were observed. A reaction conducted in equimolar H2O and D2O showed 2.7 times greater incorporation of hydrogen atom as compared to deuterium. This is consistent with the H+ and D+ ion concentrations in H2O and D2O, respectively. With appropriately deuterated precursors, partially to fully deuterated triazoles were assembled where the final deuterium atom was incorporated in the triazole-forming step.