1-[4-(tert-butyl)phenyl]-2-diazoethanone | 3488-46-8

• 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: 1-[4-(tert-butyl)phenyl]-2-diazoethanone
• 英文别名: 1-(4-(tert-butyl)phenyl)-2-diazoethan-1-one；2-<4-tert.-Butyl-phenyl>-2-oxo-diazoethan；p-tert-Butyl-α-diazo-acetophenon；1-(4-tert-Butyl-phenyl)-2-diazo-aethanon；1-(4-Tert-butyl-phenyl)-2-diazo-ethanone；1-(4-tert-butylphenyl)-2-diazoethanone
• CAS: 3488-46-8
• 化学式: C₁₂H₁₄N₂O
• 分子量: 202.256
• InChiKey: NQQOGUWJUGFNRF-UHFFFAOYSA-N

物化性质

• 熔点：
  82.5-83.5 °C

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  19.1
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2927000090

反应信息

• 作为反应物：
  描述：

  1-[4-(tert-butyl)phenyl]-2-diazoethanone 在 silver(l) oxide 作用下， 以 1,4-二氧六环 为溶剂， 生成 4-叔丁基苯乙酸
  参考文献：
  名称：

  Quinolones as gonadotropin releasing hormone (GnRH) antagonists: simultaneous optimization of the C(3)-aryl and C(6)-substituents

  摘要：

  A series of 3-arylquinolones was prepared and evaluated for their ability to act as gonadotropin releasing hormone (GnRH) antagonists. A variety of substitution patterns of the 3-aryl substituent are described. The 3,4,5-trimethylphenyl substituent (23h) was found to he optimal. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00318-8
• 作为产物：
  描述：

  2-溴-1-(4-叔丁基苯基)-乙酮 生成 1-[4-(tert-butyl)phenyl]-2-diazoethanone
  参考文献：
  名称：

  Hauptmann,S. et al., Angewandte Chemie, 1965, vol. 77, p. 678 - 679

  摘要：

  DOI：

文献信息

• Chemoselective Hydro(Chloro)pentafluorosulfanylation of Diazo Compounds with Pentafluorosulfanyl Chloride
  作者：Jia‐Yi Shou、Xiu‐Hua Xu、Feng‐Ling Qing

  DOI：10.1002/anie.202103606

  日期：2021.7.5

  demonstrated through the unprecedented reaction with diazo compounds. The chemoselective hydro- and chloropentafluorosulfanylations of α-diazo carbonyl compounds were developed in the presence of K3PO4 or copper catalyst, respectively. These reactions provide a direct and efficient access to various α-pentafluorosulfanyl carbonyl compounds of high value for potential applications.

  五氟硫酰氯 (SF 5 Cl) 是将 SF 5基团结合到有机化合物中的最常用试剂。然而，SF 5 Cl的制备通常依赖于危险的试剂和专门的仪器。在本文中，我们描述了一个台架稳定的安全和实用的合成和SF的易于手柄溶液5在含Cl Ñ正己烷气体试剂-自由条件下进行。SF 5 Cl的合成应用通过与重氮化合物的前所未有的反应得到证明。在 K 3 PO 4存在下开发了 α-重氮羰基化合物的化学选择性氢和氯五氟磺基化反应或铜催化剂，分别。这些反应为获得各种具有高价值的 α-五氟硫基羰基化合物提供了直接有效的途径，可用于潜在应用。
• Cycloaddition Reactions of Alkene Radical Cations using Iron(III)‐Phenanthroline Complex
  作者：Yong Hyun Cho、Jae Hyung Kim、Hyeju An、Kwang‐Hyun Ahn、Eun Joo Kang

  DOI：10.1002/adsc.202000191

  日期：2020.5.26

  oxidation of electron‐rich alkenes using the iron(III)‐phenanthroline complex produced electrophilic alkene radical cations, which promoted efficient radical cation [2+1] cycloaddition reactions with diazo compounds. Subsequent chain propagation afforded tri‐ and tetra‐substituted cyclopropanes. This methodology was also expanded to [3+2] cycloaddition reactions with vinyl diazoesters, validating this sustainable

  使用铁（III）-菲咯啉配合物对富电子烯烃进行单电子氧化可产生亲电子烯烃自由基阳离子，从而促进了重氮化合物与自由基阳离子[2 + 1]的高效环加成反应。随后的链增长得到三和四取代的环丙烷。该方法还扩展到了与乙烯基重氮酯的[3 + 2]环加成反应，验证了这种可持续的第一行过渡金属铁系统的单电子氧化还原反应。
• Tandem Synthesis of α-Diazoketones from 1,3-Diketones
  作者：Jianlan Zhang、Wenwen Chen、Dayun Huang、Xiaobao Zeng、Xinyan Wang、Yuefei Hu

  DOI：10.1021/acs.joc.7b01187

  日期：2017.9.1

  A highly efficient synthesis of α-diazoketone was achieved by simply stirring the mixture of 1,3-diketone, TsN3, and MeNH2 in EtOH. It was a tandem reaction including a novel primary amine-catalyzed Regitz diazo transfer of 1,3-diketone and a novel primary amine-mediated C–C bond cleavage of 2-diazo-1,3-diketone.

  通过简单地在EtOH中搅拌1,3-二酮，TsN 3和MeNH 2的混合物即可实现α-二氮酮的高效合成。这是一个串联反应，包括新型伯胺催化的1,3-二酮的Regitz重氮转移和新型伯胺介导的2-重氮1,3-二酮的C-C键裂解。
• Oxidative Coupling of Diazo and NH₄I: A Route to Primary Oxamates and α-Ketoamides
  作者：Hanghang Wang、Yanwei Zhao、Yonggao Zheng、Shangwen Fang、Jingjing Li、Xiaobing Wan

  DOI：10.1021/acs.joc.9b02952

  日期：2020.3.6

  A simple and efficient method has been developed for the preparation of primary oxamates and α-ketoamides through the oxidative coupling of diazo compounds and NH4I. Under the optimized reaction conditions, a range of diazoesters and α-diazoketones was explored, and the corresponding products were obtained in moderate to good yields. This protocol is metal-free, is performed under mild conditions,

  通过重氮化合物与NH4I的氧化偶合，已开发出一种简单有效的方法来制备伯草酸酯和α-酮酰胺。在优化的反应条件下，探索了一系列重氮酯和α-重氮酮，并以中等至良好的收率获得了相应的产物。该协议不含金属，可在温和条件下执行，具有广泛的基材范围，并且操作简便。
• Synthesis of 2,3-Disubstituted Quinolines via Ketenimine or Carbodiimide Intermediates
  作者：Hongyang Zhao、Yanpeng Xing、Ping Lu、Yanguang Wang

  DOI：10.1002/chem.201603074

  日期：2016.10.10

  ethylphenyl) phosphanimine, respectively. The reaction proceeds in a cascade involving ketenimine formation, 6 π‐electron ring closure, and 1,3‐alkyl shift. A similar approach was developed for the synthesis of dihydropyrrolo‐[2,3‐b]quinolines from N‐(2‐cyclopropylidenemethylphenyl)phosphanimines and isocyanates.

  环戊[ b ]喹啉和环己[ b ]喹啉分别通过α-重氮酮与N-（2-环亚丙基甲基苯基）膦酰胺和N-（2-环丁烯甲基苯基）膦酰胺的反应制备。该反应以级联反应进行，涉及形成烯酮亚胺，6个π电子闭环和1,3-烷基转移。还开发了一种类似的方法，用于从N-（2-环亚丙基甲基苯基）膦酰胺和异氰酸酯合成二氢吡咯并- [2,3- b ]喹啉。