N-(2-methoxy-phenyl)-hydrazinecarboxylic acid tert-butyl ester | 380383-87-9

• 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: N-(2-methoxy-phenyl)-hydrazinecarboxylic acid tert-butyl ester
• 英文别名: 1-tert-butoxycarbonyl-1-(2-methoxyphenyl)hydrazine；tert-butyl N-amino-N-(2-methoxyphenyl)carbamate
• CAS: 380383-87-9
• 化学式: C₁₂H₁₈N₂O₃
• 分子量: 238.287
• InChiKey: ODRKCHGMFLUCHU-UHFFFAOYSA-N

物化性质

• 沸点：
  336.3±44.0 °C(Predicted)
• 密度：
  1.144±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  64.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2-methoxy-phenyl)-hydrazinecarboxylic acid tert-butyl ester 在 palladium diacetate 、 三叔丁基膦 copper(l) iodide 、 caesium carbonate 作用下， 以 正己烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 5.5h， 生成
  参考文献：
  名称：

  Synthesis of Novel 1,3,5-Tris(arylazo)benzenes via Pd-Catalyzed Couplings and Cu(I)-Mediated Direct Oxidations

  摘要：

  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.

  DOI：

  10.1021/jo035720d
• 作为产物：
  描述：

  肼基甲酸叔丁酯 、 2-碘苯甲醚 在 copper(l) iodide 、 1,10-菲罗啉 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 以23%的产率得到N-(2-methoxy-phenyl)-hydrazinecarboxylic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of N-Aryl Hydrazides by Copper-Catalyzed Coupling of Hydrazides with Aryl Iodides

  摘要：

  [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.

  DOI：

  10.1021/ol0168216

文献信息

• Expedient synthesis of indoles from N-Boc arylhydrazines
  作者：Young-Kwan Lim、Cheon-Gyu Cho

  DOI：10.1016/j.tetlet.2004.01.011

  日期：2004.2

  The readily available N-Boc arylhydrazines undergo efficient Fischer cyclizations to provide the indoles in good yields, when reacted with enolizable ketones.

  当与可烯醇化的酮反应时，容易获得的N- Boc芳基肼经过有效的Fischer环化反应，以高收率提供吲哚。
• Regioselective [5,5]-Sigmatropic Rearrangement Reactions of Aryl Hydrazides
  作者：Hong-Min Kang、Young-Kwan Lim、In-Jee Shin、Hee-Yeon Kim、Cheon-Gyu Cho

  DOI：10.1021/ol060451+

  日期：2006.5.1

  N,N'-Aryl hydrazides with substituents at the ortho or meta positions undergo highly regioselective [5,5]-sigmatropic rearrangement reactions to furnish benzidines in good to excellent isolated yields. The presence of single substituent at either the ortho or meta position provides sufficient bias, effectively suppressing the formation of diphenylene, the major byproduct of the conventional benzidine rearrangement reaction.