2-(2-benzylidenehydrazinyl)-N,N,N-trimethyl-2-oxoethaneaminium chloride | 6958-22-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(2-benzylidenehydrazinyl)-N,N,N-trimethyl-2-oxoethaneaminium chloride
• 英文别名: Benzaldehyd-Girard-T-hydrazon；Carboxymethyl-trimethyl-ammonium-chlorid-；Benzaldehyd(carbohydrazonmethyl)trimethylammoniumchlorid, Benzaldehyd G-T；N-Benzylidene-2-(trimethylazaniumyl)ethanehydrazonate--hydrogen chloride (1/1)；N-benzylidene-2-(trimethylazaniumyl)ethanehydrazonate;hydrochloride
• CAS: 6958-22-1
• 化学式: C₁₂H₁₈N₃O*Cl
• 分子量: 255.747
• InChiKey: FJQGAAUWLWKTBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.15
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-benzylidenehydrazinyl)-N,N,N-trimethyl-2-oxoethaneaminium chloride 以 水 为溶剂， 生成 吉拉尔特试剂 T 、 苯甲醛
  参考文献：
  名称：

  Kinetics and mechanism of benzaldehyde Girard T hydrazone formation

  摘要：

  In aqueous solution, Girard T hydrazone formation from para-substituted benzaldehydes does not proceed to completion under the conditions used. The corresponding equilibrium constants were determined and employed to calculate the rate of the reaction at completion. For all the reactions studied, the pH-rate profiles, extrapolated to zero buffer concentration, show one break at pH 4-5, characteristic of a change in the rate-determining step from carbinolamine dehydration to carbinolamine formation upon going from pH 7 to pH 1. The formation of the carbinolamine is subject to catalysis by hydronium ion and by carboxylic acids present in the buffers used to maintain pH. Bronsted alpha values for this catalysis varied from 0.19 to 0.37. Rate constants for the cyanoacetic, chloroacetic, and formic acid catalyzed formation of carbinolamine from the para-substituted benzaldehydes correlate with sigma-+ substituent constants, giving a value of rho-+ equal to 0.70. Rate constants for the hydronium ion catalyzed formation of the carbinolamine from the same benzaldehydes are, however, insensitive to the substituent effect. These observations lead to the conclusion that the reactions occur by different routes as a function of the catalyst. We suggest a stepwise preassociation mechanism for the reaction catalyzed by carboxylic acids and a concerted preassociation mechanism for that catalyzed by hydronium ion.

  DOI：

  10.1021/jo00004a016
• 作为产物：
  描述：

  吉拉尔特试剂 T 、 苯甲醛 以 甲醇 为溶剂， 生成 2-(2-benzylidenehydrazinyl)-N,N,N-trimethyl-2-oxoethaneaminium chloride
  参考文献：
  名称：

  增强exchange交换过程的动力学：一项实验和计算研究

  摘要：

  dynamic键易于经历组分交换过程的能力在动态组合化学中得到了广泛的应用。pH交换的动力学在pH约为4.5时是最佳的，这限制了使用为基础的动态组合文库，特别是对于仅在接近中性pH值下稳定的生物靶标。因此如果在接近中性的pH值下以更快的速率进行交换将是有利的。我们通过实验和计算评估了以下假设：在羰基衍生的mo原子内具有相邻的酸性或碱性官能团，会提高交换速率。我们的工作表明，明智地放置N-或Othe的羰基衍生部分中的β-氢键受体通过氢键相互作用稳定过渡态，为在接近中性pH值下的交换动力学提供了宝贵的推动力。我们预计这些发现将在动态组合化学，动态共价聚合物/材料，功能化的纳米粒子和互锁分子中引起人们的兴趣，所有这些都可能受益于能够在接近中性pH值的条件下进行的exchange交换过程。

  DOI：

  10.1039/c9ob00058e

文献信息

• Column Chromatography-Free Solution-Phase Synthesis of a Natural Piper-Amide-like Compound Library
  作者：Sumin Kim、Chaemin Lim、Sukjin Lee、Seokwoo Lee、Hyunkyung Cho、Joo-Youn Lee、Dong Sup Shim、Hee Dong Park、Sanghee Kim

  DOI：10.1021/co400003d

  日期：2013.4.8

  We have achieved an efficient solution-phase parallel synthesis of a library of natural piper-amide-like compounds from the bifunctional beta-phosphono-N-hydroxy-succinimidyl ester intermediate. The primary important feature in our study is the construction of natural-product-like molecules through the adaptation of sophisticated organic reactions that create water-soluble byproducts for a chromatography-free purification. This simple and efficient method rapidly provides a combinatorial library of high yield and purity. The library was evaluated against GPCR targets to demonstrate its potential use as a tool for drug discovery and in chemical biology.