tert-butyl 2-(4-nitrophenyl)-2-phenylhydrazinecarboxylate

• 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: tert-butyl 2-(4-nitrophenyl)-2-phenylhydrazinecarboxylate
• 英文别名: tert-butyl N-(N-(4-nitrophenyl)anilino)carbamate
• 化学式: C₁₇H₁₉N₃O₄
• 分子量: 329.356
• InChiKey: OTLLKEJMBJAOCP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  87.4
• 氢给体数：
  1
• 氢受体数：
  5

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  肼基甲酸-o-叔丁基-n-4-硝基苯酯	tert-butyl 2-(4-nitrophenyl)hydrazine-1-carboxylate	92491-67-3	C11H15N3O4	253.258

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-(4-nitrophenyl)-2-phenylhydrazinecarboxylate 在 10% Pd/C 、 氢气 、 溶剂黄146 作用下， 以 甲醇 、 甲苯 为溶剂， 生成 tert-butyl 2-(4-((4-(ethoxycarbonyl)phenyl)diazenyl)phenyl)-2-phenylhydrazinecarboxylate
  参考文献：
  名称：

  Fluorescence Quenchers for Hydrazone and Oxime Orthogonal Bioconjugation

  摘要：

  We describe the synthesis and properties of new fluorescence quenchers containing aldehyde, hydrazine, and aminooxy groups, allowing convenient bioconjugation as oximes or hydrazones. Conjugation to oligonucleotides proceeded in high yield with aniline as catalyst. Kinetics studies of conjugation show that, under optimal conditions, a hydrazine or aminooxy quencher can react with aldehyde-modified DNA to form a stable hydrazone or oxime adduct in as little as five minutes. The resulting quencher-containing DNAs were assessed for their ability to quench the emission of fluorescein in labeled complements and compared to the commercially available dabcyl and Black Hole Quencher 2 (BHQ2), which were conjugated as phosphoramidites. Results show that the new quenchers possess slightly different absorbance properties compared to dabcyl and are as efficient as the commercial quenchers in quenching fluorescein emission. Hydrazone-based quenchers were further successfully incorporated into molecular beacons and shown to give high signal to background ratios in single nucleotide polymorphism detection in vitro. Finally, aminooxy and hydrazine quenchers were applied to quenching of an aldehyde-containing fluorophore associated with living cells, demonstrating cellular quenching within one hour.

  DOI：

  10.1021/bc300344b
• 作为产物：
  描述：

  4-硝基苯肼盐酸盐 在 4-二甲氨基吡啶 、 三乙胺 、 copper(l) chloride 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 2.67h， 生成 tert-butyl 2-(4-nitrophenyl)-2-phenylhydrazinecarboxylate
  参考文献：
  名称：

  CuCl和DMAP催化2-苯基苯肼羧酸烷基酯的好氧氧化

  摘要：

  近来，由于2-苯基偶氮羧酸烷基酯，报道了各种富有成效的有机反应，例如催化的Mitsunobu反应，但是，2-苯基偶氮羧酸烷基酯的合成很大程度上取决于有毒氧化剂的化学计量使用。在该手稿中，公开了一种环境友好的2-苯基肼甲酸烷基酯的好氧氧化转化为2-苯基偶氮羧酸烷基酯的方法。在温和条件下，使用CuCl和DMAP系统可有效催化2-苯基肼甲酸烷基酯的需氧氧化。本发明的铜催化反应速率比以前报道的铁催化速率快得多，并且在3小时内合成了多种偶氮产物。本协议在更大范围内是有效的。

  DOI：

  10.1021/acs.joc.7b03119

文献信息

• Addition of Arylboronic Acids to Symmetrical and Unsymmetrical Azo Compounds
  作者：Ksenija Kisseljova、Olga Tšubrik、Rannar Sillard、Sirje Mäeorg、Uno Mäeorg

  DOI：10.1021/ol052403f

  日期：2006.1.1

  [reaction: see text] The addition of aryl- and heteroarylboronic acids to azo compounds is described. Copper salt catalysis was necessary to perform the reaction under mild conditions and high yields. Excellent regioselectivity was observed in addition to unsymmetrical azo compounds.

  [反应：见正文]描述了向偶氮化合物中添加芳基硼酸和杂芳基硼酸。铜盐催化对于在温和的条件下以高收率进行反应是必要的。除了不对称的偶氮化合物外，还观察到了优异的区域选择性。
• Copper Salt Catalyzed Coupling of Organobismuth Reagents and Azo Compounds
  作者：Uno Mäeorg、Olga Tšubrik、Ksenija Kisseljova

  DOI：10.1055/s-2006-950408

  日期：2006.9

  A new copper salt catalyzed C-N coupling is described. This smooth reaction between azo compounds and organobismuth reagents provides efficient and highly regioselective access to Boc-protected aryl hydrazines. The yields under optimized conditions are mostly excellent and the synthetic procedure is robust and simple.

  描述了一种新的铜盐催化 CN 偶联。偶氮化合物与有机铋试剂之间的这种平稳反应为获得 Boc 保护的芳基肼提供了高效且高度区域选择性的途径。优化条件下的产率大多非常好，合成过程稳健且简单。
• Aerobic Oxidation of Alkyl 2-Phenylhydrazinecarboxylates Catalyzed by CuCl and DMAP
  作者：Min Hye Kim、Jinho Kim

  DOI：10.1021/acs.joc.7b03119

  日期：2018.2.2

  various fruitful organic reactions such as a catalytic Mitsunobu reaction were reported by virtue of alkyl 2-phenylazocarboxylates, however, the synthesis of alkyl 2-phenylazocarboxylates largely depended on the stoichiometric use of toxic oxidants. In this manuscript, an environment-friendly aerobic oxidative transformation of alkyl 2-phenylhydrazinecarboxylates to alkyl 2-phenylazocarboxylates is

  近来，由于2-苯基偶氮羧酸烷基酯，报道了各种富有成效的有机反应，例如催化的Mitsunobu反应，但是，2-苯基偶氮羧酸烷基酯的合成很大程度上取决于有毒氧化剂的化学计量使用。在该手稿中，公开了一种环境友好的2-苯基肼甲酸烷基酯的好氧氧化转化为2-苯基偶氮羧酸烷基酯的方法。在温和条件下，使用CuCl和DMAP系统可有效催化2-苯基肼甲酸烷基酯的需氧氧化。本发明的铜催化反应速率比以前报道的铁催化速率快得多，并且在3小时内合成了多种偶氮产物。本协议在更大范围内是有效的。
• Fluorescence Quenchers for Hydrazone and Oxime Orthogonal Bioconjugation
  作者：Pete Crisalli、Armando R. Hernández、Eric T. Kool

  DOI：10.1021/bc300344b

  日期：2012.9.19

  We describe the synthesis and properties of new fluorescence quenchers containing aldehyde, hydrazine, and aminooxy groups, allowing convenient bioconjugation as oximes or hydrazones. Conjugation to oligonucleotides proceeded in high yield with aniline as catalyst. Kinetics studies of conjugation show that, under optimal conditions, a hydrazine or aminooxy quencher can react with aldehyde-modified DNA to form a stable hydrazone or oxime adduct in as little as five minutes. The resulting quencher-containing DNAs were assessed for their ability to quench the emission of fluorescein in labeled complements and compared to the commercially available dabcyl and Black Hole Quencher 2 (BHQ2), which were conjugated as phosphoramidites. Results show that the new quenchers possess slightly different absorbance properties compared to dabcyl and are as efficient as the commercial quenchers in quenching fluorescein emission. Hydrazone-based quenchers were further successfully incorporated into molecular beacons and shown to give high signal to background ratios in single nucleotide polymorphism detection in vitro. Finally, aminooxy and hydrazine quenchers were applied to quenching of an aldehyde-containing fluorophore associated with living cells, demonstrating cellular quenching within one hour.