acrylamidine | 19408-49-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: acrylamidine
• 英文别名: Prop-2-enimidamide
• CAS: 19408-49-2
• 化学式: C₃H₆N₂
• mdl: MFCD19205439
• 分子量: 70.094
• InChiKey: AXPUQAAUHKSVKR-UHFFFAOYSA-N

物化性质

• 沸点：
  86.4±23.0 °C(Predicted)
• 密度：
  0.96±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  5
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.9
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  acrylamidine 在 次氯酸 、 sodium chloride 作用下， 以 二甲基亚砜 为溶剂， 生成 vinylchlorodiazirine
  参考文献：
  名称：

  Singlet Vinylcarbenes:  Spectroscopy and Photochemistry

  摘要：

  The first direct spectroscopic characterization of singlet vinylcarbenes is reported. Several vinyl amidines were converted to the corresponding vinylchlorodiazirines through straightforward Graham oxidation. Irradiation of the diazirines at 8 K in N2 matrices gave the corresponding singlet vinylchlorocarbenes, which could be characterized by IR, UV/vis, and calculational modeling. Hence, vinylchlorocarbene, 1-methylvinylchlorocarbene, and 1-cyclopentenylchlorocarbene were all generated and investigated. The spectra are consistent with localized carbene structures compared to the very delocalized triplet vinylcarbenes. In all cases, the carbenes readily cyclize to the corresponding cyclopropenes on visible irradiation, together with H-shift in the parent vinylchlorocarbene. In the cyclopentenyl system, cyclization leads to a highly strained bicyclo[3.1.0]hexene.

  DOI：

  10.1021/ja046309q
• 作为产物：
  描述：

  丙烯腈 在 三甲基铝 、 氯化铵 作用下， 以 甲苯 为溶剂， 反应 17.0h， 以39%的产率得到acrylamidine
  参考文献：
  名称：

  甲基精氨酸类似物在重组组蛋白中的位点特异性和区域特异性安装以及对效应蛋白结合的深入了解

  摘要：

  精氨酸甲基化已成为广泛的翻译后修饰，对无数细胞过程产生影响。然而，这种甲基精氨酸依赖性现象背后的分子机制仍不清楚。为了帮助这项研究，开发了一种简便的方法，将甲基精氨酸类似物安装在重组蛋白上，用于生物化学、生物物理和结构研究。通过新型 α,β-不饱和脒前体与蛋白质的化学偶联，甲基精氨酸模拟物可以通过控制甲基化位点、程度和区域特异性来展示。使用这种策略将类似物安装到组蛋白中产生了被内源性甲基精氨酸特异性抗体识别的修饰蛋白，并且这些组蛋白保留了形成单核小体的能力。而且，显示天然甲基精氨酸特异性结合域与甲基精氨酸类似物修饰的底物相互作用。这种用于安装甲基精氨酸类似物的化学缀合方法提供了一种生产均质修饰蛋白的有效途径，用于随后研究甲基精氨酸依赖性过程。

  DOI：

  10.1021/ja3108214

文献信息

• An efficient conversion of nitriles to amidines
  作者：Ravi S. Garigipati

  DOI：10.1016/s0040-4039(00)88891-7

  日期：1990.1

  A convenient method has been developed for direct conversion of nitriles to amidines in high yields. The method can also be applied to the preparation of guanidines from N-alkyl cyanamides.

  已经开发了一种方便的方法，用于以高收率将腈直接转化为am。该方法还可用于由N-烷基氰酰胺制备胍。
• Disease-Causing Mutations in the G Protein Gαs Subvert the Roles of GDP and GTP
  作者：Qi Hu、Kevan M. Shokat

  DOI：10.1016/j.cell.2018.03.018

  日期：2018.5

  The single most frequent cancer-causing mutation across all heterotrimeric G proteins is R201C in G alpha s. The current model explaining the gain-of-function activity of the R201 mutations is through the loss of GTPase activity and resulting inability to switch off to the GDP state. Here, we find that the R201C mutation can bypass the need for GTP binding by directly activating GDP-bound G alpha s through stabilization of an intramolecular hydrogen bond network. Having found that a gain-of-function mutation can convert GDP into an activator, we postulated that a reciprocal mutation might disrupt the normal role of GTP. Indeed, we found R228C, a loss-of-function mutation in G alpha s that causes pseudohypoparathyroidism type 1a (PHP-Ia), compromised the adenylyl cyclase-activating activity of G alpha s bound to a non-hydrolyzable GTP analog. These findings show that disease-causing mutations in G alpha s can subvert the canonical roles of GDP and GTP, providing new insights into the regulation mechanism of G proteins.
• GARIGIPATI, RAVI S., TETRAHEDRON LETT., 31,(1990) N4, C. 1969-1972
  作者：GARIGIPATI, RAVI S.

  DOI：——

  日期：——
• Singlet Vinylcarbenes:  Spectroscopy and Photochemistry
  作者：Peter S. Zuev、Robert S. Sheridan

  DOI：10.1021/ja046309q

  日期：2004.10.1

  The first direct spectroscopic characterization of singlet vinylcarbenes is reported. Several vinyl amidines were converted to the corresponding vinylchlorodiazirines through straightforward Graham oxidation. Irradiation of the diazirines at 8 K in N2 matrices gave the corresponding singlet vinylchlorocarbenes, which could be characterized by IR, UV/vis, and calculational modeling. Hence, vinylchlorocarbene, 1-methylvinylchlorocarbene, and 1-cyclopentenylchlorocarbene were all generated and investigated. The spectra are consistent with localized carbene structures compared to the very delocalized triplet vinylcarbenes. In all cases, the carbenes readily cyclize to the corresponding cyclopropenes on visible irradiation, together with H-shift in the parent vinylchlorocarbene. In the cyclopentenyl system, cyclization leads to a highly strained bicyclo[3.1.0]hexene.
• Site-Specific and Regiospecific Installation of Methylarginine Analogues into Recombinant Histones and Insights into Effector Protein Binding
  作者：Daniel D. Le、Arianna T. Cortesi、Samuel A. Myers、Alma L. Burlingame、Danica Galonić Fujimori

  DOI：10.1021/ja3108214

  日期：2013.2.27

  install methylarginine analogues on recombinant protein for use in biochemical, biophysical, and structural studies. Through chemical conjugation of novel α,β-unsaturated amidine precursors with proteins, methylarginine mimics can be displayed with control of methylation site, extent, and regiospecificity. Analogue installation into histones using this strategy produced modified proteins that were recognized

  精氨酸甲基化已成为广泛的翻译后修饰，对无数细胞过程产生影响。然而，这种甲基精氨酸依赖性现象背后的分子机制仍不清楚。为了帮助这项研究，开发了一种简便的方法，将甲基精氨酸类似物安装在重组蛋白上，用于生物化学、生物物理和结构研究。通过新型 α,β-不饱和脒前体与蛋白质的化学偶联，甲基精氨酸模拟物可以通过控制甲基化位点、程度和区域特异性来展示。使用这种策略将类似物安装到组蛋白中产生了被内源性甲基精氨酸特异性抗体识别的修饰蛋白，并且这些组蛋白保留了形成单核小体的能力。而且，显示天然甲基精氨酸特异性结合域与甲基精氨酸类似物修饰的底物相互作用。这种用于安装甲基精氨酸类似物的化学缀合方法提供了一种生产均质修饰蛋白的有效途径，用于随后研究甲基精氨酸依赖性过程。