N',N'-二甲基-2-呋喃甲酰肼 | 159239-28-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 中文名称: N',N'-二甲基-2-呋喃甲酰肼
• 英文名称: 1-(2-furoyl)-2,2-dimethylhydrazine
• 英文别名: N',N'-dimethylfuran-2-carbohydrazide
• CAS: 159239-28-8
• 化学式: C₇H₁₀N₂O₂
• mdl: MFCD23714207
• 分子量: 154.169
• InChiKey: MQHIGAOPSIGEGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N',N'-二甲基-2-呋喃甲酰肼 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 48.0h， 生成 bis(N,N-dimethyl-N'-2-furoylhydrazonium)-N-hexamethylene aminimide
  参考文献：
  名称：

  Uphill Transport of Metal Picrate through a Liquid Membrane by Ylides

  摘要：

  New pH dependent carrier molecules, aminimides, were synthesized, and their properties were investigated by transport experiments of metal picrate through a liquid membrane. These aminimides have the nitrogen atom bearing a negative charge (ylidic nitrogen atom) and the oxygen atom of the carbonyl group, which interact with metal ions. Since this ylidic nitrogen atom can interact with a proton in solution and be conjugated to the carbonyl group, the extraction equilibrium constant is affected by the substituents of the aminimide and the pH in solution. Thus, the transport rate of metal picrate by the aminimide depended on the substituents and the pH in solution. By using this property of aminimides, a new uphill transport system was constructed and it was found that aminimides are efficient carrier molecules to transport metal picrate against its concentration gradient. The numerical simulation of uphill transport by this pH dependent carrier has been performed by using the improved transport rate equation, and the calculated result is consistent with the experimental result. These results indicate that the uphill transport arises from the difference in the extraction equilibrium constant at the two interfaces between the organic phase and the aqueous phases with different pH values.

  DOI：

  10.1021/j100102a039
• 作为产物：
  描述：

  呋喃甲酰氯 、 偏二甲肼 以 二氯甲烷 为溶剂， 反应 3.75h， 以1.64 g的产率得到N',N'-二甲基-2-呋喃甲酰肼
  参考文献：
  名称：

  用于电化学 C-H 氧化的 N-铵叶立德介体

  摘要：

  强 C(sp 3 )-H 键的位点特异性氧化在有机合成中具有无可争议的效用。从简化对代谢物的获取和先导化合物的后期多样化到截断逆合成计划，学术界和工业界都越来越需要新的试剂和方法来实现这种转变。当前化学试剂的一个主要缺点是在结构和反应性方面缺乏多样性，这阻碍了用于快速筛选的组合方法的使用。在这方面，定向进化仍然最有希望在各种复杂环境中实现复杂的 C-H 氧化。在此，我们提出了一个设计合理的平台，该平台使用N-铵叶立德作为电化学驱动的氧化剂，用于位点特异性、化学选择性 C(sp 3 )-H 氧化。通过采用以计算为指导的第一性原理方法，这些新的介质被识别出来，并使用无处不在的构建块和简单的合成技术迅速扩展到一个库中。基于叶立德的 C-H 氧化方法表现出可调的选择性，这通常是此类氧化剂独有的，可应用于农业和制药领域的实际问题。

  DOI：

  10.1021/jacs.1c03780

文献信息

• N,N-Dialkylation of Acyl Hydrazides with Alcohols Catalyzed by Amidato Iridium Complexes via Borrowing Hydrogen
  作者：Wan-Hui Wang、Wei-Yu Shao、Jia-Yue Sang、Xu Li、Xiaoqiang Yu、Yoshinori Yamamoto、Ming Bao

  DOI：10.1021/acs.organomet.3c00026

  日期：2023.9.25

  Direct N,N-dialkylation of acyl hydrazide catalyzed by a series of amidato iridium complexes bearing an electron-donating group in the ligand using methanol or ethanol as the alkyl reagent under weak base conditions (10 mol % KHCO3) is described. A wide range of acyl hydrazide derivatives are converted to the corresponding N,N-dialkylated products in excellent yields (38 examples, yields of ≤96%).

  描述了在弱碱条件（10 mol% KHCO 3）下，使用甲醇或乙醇作为烷基试剂，由一系列配体中带有给电子基团的酰胺铱络合物催化酰肼的直接N,N-二烷基化反应。多种酰肼衍生物均以优异的收率转化为相应的 N,N-二烷基化产物（38 个实例，收率≤96%）。在对照实验和核磁共振研究的基础上，提出了一种合理的机制。实验结果表明，吡啶甲酰胺配体的苯基部分上的邻位给电子基团在催化活性中起着至关重要的作用。
• Reactions of 1-[Benzoyl(2-hetaroyl)]-2,2-dimethyhydrazines with 1,3-Dibromopropyne, 2-Propynyl Bromide, and Allyl Bromide
  作者：A. S. Nakhmanovich、R. V. Karnaukhova、L. I. Larina、P. E. Ushakov、V. A. Lopyrev

  DOI：10.1023/b:rujo.0000013127.32367.38

  日期：2003.11

  Reactions of 1-[benzoyl(2-hetaroyl)]-2,2-dimethyhydrazines with 1,3-dibromopropyne in MeOH at 50degreesC afforded 2-phenyl(heteryl)-6-bromomethylidene-4,4-dimethyl-5H-1,3,4-oxadiazinium bromides. Reactions of 1-[benzoyl(2-hetaroyl)]-2,2-dimethyhydrazines with propargyl bromide and allyl bromide gave rise to 1,1-dimethyl-1-(2-propyn-l-yl)- and 1,1-dimethyl-1-(2-propen-1-yl)-2-benzoyl(hetaroyl)hydrazinium bromides. On treating these compounds with NaOH solution the corresponding imides were obtained.
• Chemotherapy of Experimental Tuberculosis. VIII. The Synthesis of Acid Hydrazides, their Derivatives and Related Compounds^1,2
  作者：Harry L. Yale、Kathryn Losee、Joseph Martins、Mary Holsing、Frances M. Perry、Jack Bernstein

  DOI：10.1021/ja01104a046

  日期：1953.4
• Dialkylhydrazides for directed orthometalations
  作者：Scott A Pratt、Michael P Goble、Michael J Mulvaney、Peter G.M Wuts

  DOI：10.1016/s0040-4039(00)00462-7

  日期：2000.5

  Dimethylhydrazides are shown to be excellent substrates for the directed orthometalation reaction. The advantage of using the hydrazide is that it is easily removed by treatment with H5IO6 or CuCl2 to give the carboxylic acid under very mild conditions, in contrast to other amides that generally require harshly acidic conditions to achieve hydrolysis. (C) 2000 Elsevier Science Ltd. All rights reserved.
• <i>N</i>-Ammonium Ylide Mediators for Electrochemical C–H Oxidation
  作者：Masato Saito、Yu Kawamata、Michael Meanwell、Rafael Navratil、Debora Chiodi、Ethan Carlson、Pengfei Hu、Longrui Chen、Sagar Udyavara、Cian Kingston、Mayank Tanwar、Sameer Tyagi、Bruce P. McKillican、Moses G. Gichinga、Michael A. Schmidt、Martin D. Eastgate、Massimiliano Lamberto、Chi He、Tianhua Tang、Christian A. Malapit、Matthew S. Sigman、Shelley D. Minteer、Matthew Neurock、Phil S. Baran

  DOI：10.1021/jacs.1c03780

  日期：2021.5.26

  taking a first-principles approach guided by computation, these new mediators were identified and rapidly expanded into a library using ubiquitous building blocks and trivial synthesis techniques. The ylide-based approach to C–H oxidation exhibits tunable selectivity that is often exclusive to this class of oxidants and can be applied to real-world problems in the agricultural and pharmaceutical sectors

  强 C(sp 3 )-H 键的位点特异性氧化在有机合成中具有无可争议的效用。从简化对代谢物的获取和先导化合物的后期多样化到截断逆合成计划，学术界和工业界都越来越需要新的试剂和方法来实现这种转变。当前化学试剂的一个主要缺点是在结构和反应性方面缺乏多样性，这阻碍了用于快速筛选的组合方法的使用。在这方面，定向进化仍然最有希望在各种复杂环境中实现复杂的 C-H 氧化。在此，我们提出了一个设计合理的平台，该平台使用N-铵叶立德作为电化学驱动的氧化剂，用于位点特异性、化学选择性 C(sp 3 )-H 氧化。通过采用以计算为指导的第一性原理方法，这些新的介质被识别出来，并使用无处不在的构建块和简单的合成技术迅速扩展到一个库中。基于叶立德的 C-H 氧化方法表现出可调的选择性，这通常是此类氧化剂独有的，可应用于农业和制药领域的实际问题。