1-tert-butoxycarbonyl-1-(4-acetylphenyl)hydrazine | 226065-31-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-tert-butoxycarbonyl-1-(4-acetylphenyl)hydrazine
• 英文别名: tert-butyl 1-(4-acetylphenyl)hydrazinecarboxylate；N-(4-Acetylphenyl)carbazic acid tert-butyl ester；tert-butyl N-(4-acetylphenyl)-N-aminocarbamate
• CAS: 226065-31-2
• 化学式: C₁₃H₁₈N₂O₃
• 分子量: 250.298
• InChiKey: JLVNTJVDQRBREZ-UHFFFAOYSA-N

物化性质

• 沸点：
  386.1±44.0 °C(Predicted)
• 密度：
  1.160±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  72.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-tert-butoxycarbonyl-1-(4-acetylphenyl)hydrazine 在 silver carbonate 作用下， 以 乙二醇二甲醚 为溶剂， 反应 2.5h， 以74%的产率得到4-乙酰基苯基氨基甲酸叔丁酯
  参考文献：
  名称：

  Ag +介导的N -Boc芳基肼的脱氨基反应，可有效合成N -Boc芳基胺

  摘要：

  将N-Boc-芳基肼转化成Ñ Ag的作用下-Boc-芳基胺+。其温和的反应条件可耐受各种官能团的存在。

  DOI：

  10.1016/s0040-4039(02)01800-2
• 作为产物：
  描述：

  肼基甲酸叔丁酯 、 4-溴苯乙酮 在 tris(dibenzylideneacetone)dipalladium (0) 1,1'-双(二苯基膦)二茂铁 、 caesium carbonate 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以65%的产率得到1-tert-butoxycarbonyl-1-(4-acetylphenyl)hydrazine
  参考文献：
  名称：

  Regioselective synthesis of aryl hydrazides by palladium-catalyzed coupling of t-butylcarbazate with substituted aryl bromides

  摘要：

  Substituted aryl bromides are coupled with t-butylcarbazate in the presence of a palladium catalyst and base to afford regioselectively, the corresponding amidation product or amination product depending upon the position of the substituents on the aryl bromide. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00561-4

文献信息

• CuI/4-Hydro-<scp>l</scp>-proline as a More Effective Catalytic System for Coupling of Aryl Bromides with <i>N</i>-Boc Hydrazine and Aqueous Ammonia
  作者：Liqin Jiang、Xu Lu、Hui Zhang、Yongwen Jiang、Dawei Ma

  DOI：10.1021/jo9006738

  日期：2009.6.19

  CuI/4-hydroxy-l-proline-catalyzed coupling of aryl bromides and N-Boc hydrazine takes place in DMSO at 80 °C to give N-aryl hydrazides. When aryl iodides are employed, this reaction completes at 50 °C and no ligand is required. Under the catalysis of CuI/4-hydroxy-l-proline, the coupling reaction of aqueous ammonia with aryl bromides proceeds smoothly at 50 °C to afford primary arylamines. In this

  CuI / 4-羟基-1-脯氨酸催化的芳基溴化物与N- Boc肼的偶合反应在DMSO中于80°C进行，得到N-芳基酰肼。当使用芳基碘化物时，该反应在50℃下完成并且不需要配体。在CuI / 4-羟基-1-脯氨酸的催化下，氨水与芳基溴化物的偶联反应在50℃下顺利进行，得到伯芳基胺。在这种情况下，发现K 2 CO 3是比Cs 2 CO 3更好的碱。这些过程允许组装N带有多种官能团的-芳基酰肼和伯芳基胺包括羟基，胺基，三氟甲基，酯基，硝基和酮。
• Synthesis of <i>N</i>-Aryl Hydrazides by Copper-Catalyzed Coupling of Hydrazides with Aryl Iodides
  作者：Martina Wolter、Artis Klapars、Stephen L. Buchwald

  DOI：10.1021/ol0168216

  日期：2001.11.1

  [GRAPHICS]A convenient method for intermolecular N-arylation of hydrazides with substituted aryl iodides in the presence of a copper catalyst and Cs(2)CO(3) is reported. The C-N coupling of N-Boc hydrazine with para- and meta-substituted aryl iodides afforded the N-arylated products A, regioselectively. A reversal in regioselectivity is observed for the arylation of benzoic hydrazide with ortho-substituted aryl iodides, providing the N'-arylated products B.
• Synthesis of Novel 1,3,5-Tris(arylazo)benzenes via Pd-Catalyzed Couplings and Cu(I)-Mediated Direct Oxidations
  作者：Young-Kwan Lim、Sunju Choi、Kyung Bae Park、Cheon-Gyu Cho

  DOI：10.1021/jo035720d

  日期：2004.4.1

  A series of novel 1,3,5-tris-azobenzenes were prepared from 1,3,5-trihalobenzene via Pd-catalyzed couplings of N-Boc aryl hydrazines and subsequent Cu(I)-mediated direct oxidations. The oxidation of tris-arylhydrazide provided the azobenzene as a mixture of all four of the possible E/Z-isomers; [E,E,E]-, [E,E,Z]-, [E,Z,Z]-, and [Z,Z,Z]-1,3,5-tris-azobenzenes. A slow removal of the solvent in the dark transformed the isomers into the all-trans, [E,E,E]-isomer.
• Regioselective synthesis of aryl hydrazides by palladium-catalyzed coupling of t-butylcarbazate with substituted aryl bromides
  作者：Zhongren Wang、Renato T. Skerlj、Gary J. Bridger

  DOI：10.1016/s0040-4039(99)00561-4

  日期：1999.4

  Substituted aryl bromides are coupled with t-butylcarbazate in the presence of a palladium catalyst and base to afford regioselectively, the corresponding amidation product or amination product depending upon the position of the substituents on the aryl bromide. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Ag+ mediated deaminations of N-Boc aryl hydrazines for the efficient synthesis of N-Boc aryl amines
  作者：Kang-Sang Lee、Young-Kwan Lim、Cheon-Gyu Cho

  DOI：10.1016/s0040-4039(02)01800-2

  日期：2002.10

  N-Boc-aryl hydrazines were converted into N-Boc-aryl amines under the action of Ag+. Its mild reaction conditions tolerate the presence of a variety of functional groups.

  将N-Boc-芳基肼转化成Ñ Ag的作用下-Boc-芳基胺+。其温和的反应条件可耐受各种官能团的存在。