2-chloro-N-phenylacrylamide | 79751-44-3

• 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: 2-chloro-N-phenylacrylamide
• 英文别名: 2-chloro-acrylic acid anilide；2-Chlor-acrylsaeure-anilid；2-Chloro-N-phenyl-2-propenamide；2-chloro-N-phenylprop-2-enamide
• CAS: 79751-44-3
• 化学式: C₉H₈ClNO
• 分子量: 181.622
• InChiKey: KLQLSMICJDOHEV-UHFFFAOYSA-N

物化性质

• 熔点：
  52.5-53.5 °C
• 沸点：
  349.9±34.0 °C(Predicted)
• 密度：
  1.249±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  谷胱甘肽 、 2-chloro-N-phenylacrylamide 在 二甲基亚砜 作用下， 以 aq. phosphate buffer 为溶剂， 生成
  参考文献：
  名称：

  Systematic Study of the Glutathione Reactivity of N-Phenylacrylamides: 2. Effects of Acrylamide Substitution

  摘要：

  A comprehensive understanding of structure-reactivity relationships is critical to the design and optimization of cysteine-targeted covalent inhibitors. Herein, we report glutathione (GSH) reaction rates for N-phenyl acrylamides with varied substitutions at the α- and β-positions of the acrylamide moiety. We find that the GSH reaction rates can generally be understood in terms of the electron donating or withdrawing ability of the substituent. When installed at the β-position, aminomethyl substituents with amine pK_a's > 7 accelerate, while those with pK_a's < 7 slow the rate of GSH addition at pH 7.4, relative to a hydrogen substituent. Although a computational model was able to only approximately capture experimental reactivity trends, our calculations do not support a frequently invoked mechanism of concerted amine/thiol proton transfer and C-S bond formation and instead suggest that protonated aminomethyl functions as an electron-withdrawing group to reduce the barrier for thiolate addition to the acrylamide.

  DOI：

  10.1021/acs.jmedchem.0c00749
• 作为产物：
  描述：

  alpha-氯丙烯酰氯 、 苯胺 在 苯 作用下， 生成 2-chloro-N-phenylacrylamide
  参考文献：
  名称：

  Jakubowitsch et al., Zhurnal Obshchei Khimii, 1958, vol. 28, p. 320; engl. Ausg. S. 316

  摘要：

  DOI：

文献信息

• Photocatalytic Radical Coupling of Organoborates with α-Halogenated Electron-Poor Olefins
  作者：Marina Caldarelli、Sarah Jane Rezzi、Nicoletta Colombo、Tracey Pirali、Gianluca Papeo

  DOI：10.1021/acs.joc.3c02386

  日期：2024.1.5

  Herein, we report the visible-light-mediated addition of organoborates to α-halogenated electron-poor olefins enabled by an environmentally benign metal-free catalyst. The method accommodates a variety of boronic acid derivatives as well as alkenes and delivers the corresponding saturated α-halo-derivatives in up to 90% yields. The obtained products are high-value building blocks in organic synthesis

  在此，我们报告了通过环境友好的无金属催化剂实现的可见光介导的有机硼酸盐与α-卤代贫电子烯烃的加成。该方法适用于各种硼酸衍生物以及烯烃，并以高达 90% 的产率提供相应的饱和 α-卤代衍生物。所得产品是有机合成中的高价值构建模块，可进行各种后续转化。
• Purification of aziridine-2-carboxylic acid salts
  申请人：RESEARCH ASSOCIATION FOR UTILIZATION OF LIGHT OIL

  公开号：EP0191462A1

  公开（公告）日：1986-08-20

  Alkaline earth metal salts of aziridine-2-carboxylic acid, typically Ca salt, are produced by a reaction of a 2,3-diha- iopropionic acid derivative or an a-haloacrylic acid derivative with an aqueous ammonia in the presence of an alkaline earth metal hydroxide, typically Ca(OH)2. Salts of aziridine-2-carboxylic acid are recovered from such a reaction product as referred to above by a liquid chromatographic technique in which a weak or weakened cation exchanger is utilized.

  氮丙啶-2-羧酸的碱土金属盐，通常为 Ca 盐，是由 2,3-二哈-碘丙酸衍生物或 a-卤丙烯酸衍生物与水氨在碱土金属氢氧化物（通常为 Ca(OH)2）存在下反应生成的。
• Neidlein, Richard; Lehr, Werner, Heterocycles, 1981, vol. 16, # 7, p. 1187 - 1194
  作者：Neidlein, Richard、Lehr, Werner

  DOI：——

  日期：——
• NEIDLEIN R.; LEHR W., HETEROCYCLES, 1981, 16, NO 7, 1187-1194
  作者：NEIDLEIN R.、 LEHR W.

  DOI：——

  日期：——
• US3960948A
  申请人：——

  公开号：US3960948A

  公开（公告）日：1976-06-01