butyl-malonic acid-dianilide | 26971-94-8

• 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: butyl-malonic acid-dianilide
• 英文别名: Butyl-malonsaeure-dianilid；2-butyl-N,N'-diphenyl-propanediamide；Pentan-dicarbonsaeure-(1.1)-dianilid；Butylmalondianilid；2-butyl-N,N'-diphenylpropanediamide
• CAS: 26971-94-8
• 化学式: C₁₉H₂₂N₂O₂
• 分子量: 310.396
• InChiKey: FZWYSYLWNVPKLT-UHFFFAOYSA-N

物化性质

• 熔点：
  193 °C(Solv: ethanol (64-17-5))
• 沸点：
  568.5±33.0 °C(Predicted)
• 密度：
  1.165±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  butyl-malonic acid-dianilide 在 N-溴代丁二酰亚胺(NBS) 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 6.0h， 生成 5-(bromomethyl)-3-butyl-3-(N-phenylcarbamoyl)-2-(N-phenylimino)tetrahydrofuran
  参考文献：
  名称：

  溴亚氨基内酯的非对映异构合成：α-烯丙基丙二酰胺的电化学和化学溴亚氨基内酯化

  摘要：

  报道了通过 α-取代的 α-烯丙基丙二酰胺的溴亚氨基内酯化反应非对映异构合成 N-取代的亚氨基内酯。而在常规化学条件下溴环化提供顺式溴亚氨基内酯，电化学条件表现出互补的非对映选择性以提供反式产物。在两组条件下，氮原子上的各种取代基和丙二酰胺的 α 位都可以耐受，从而以优异的产率和高非对映选择性提供相应的亚氨基内酯。

  DOI：

  10.1055/s-0037-1611791
• 作为产物：
  描述：

  正溴丁烷 、 N,N'-二(苯基)丙二酰胺 在 potassium tert-butylate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 butyl-malonic acid-dianilide
  参考文献：
  名称：

  A Nanocrystal Catalyst Incorporating a Surface Bound Transition Metal to Induce Photocatalytic Sequential Electron Transfer Events

  摘要：

  DOI：

  10.1021/jacs.1c00503

文献信息

• Prostaglandin-H synthase inhibition by malonamides. Ring-opened analogs of phenylbutazone
  作者：Jonathan L. Vennerstrom、Thomas J. Holmes

  DOI：10.1021/jm00385a031

  日期：1987.2

  Recent reports of serious concern regarding the safe clinical use of phenylbutazone and its hydroxylated metabolite (oxyphenbutazone) as antiinflammatory agents have prompted the further investigation of ring-opened (malonamide) derivatives as potentially preferable therapeutic derivatives. Earlier reports have claimed reduced toxicity among similar derivatives. These studies reveal the relative degree of prostaglandin-H (PGH) synthase inhibitory activity among a series of malonamide derivatives. Contrary to observations in the pyrazolidinedione series, incorporation of a nonpolar butyl side chain in these malonamides was not beneficial but, rather, detrimental to enzyme-inhibitory activity. Although none of the reported nonbutylated malonamides was as potent an inhibitor of this enzyme as phenylbutazone, they all showed some inhibitory activity. PGH synthase inhibitory activity was especially pronounced in the bis(p-hydroxy anilide) derivatives, even extending to succinamide and adipamide derivatives. Of some interest is the observation that all of these p-hydroxy anilide derivatives were more potent inhibitors of this enzyme than acetaminophen.
• Dox; Yoder, Journal of the American Chemical Society, 1922, vol. 44, p. 1579
  作者：Dox、Yoder

  DOI：——

  日期：——
• SZCEZECINSKI P.; TERPINSKI J., POL. J. CHEM., 1978, 52, NO 5 1077-1078
  作者：SZCEZECINSKI P.、 TERPINSKI J.

  DOI：——

  日期：——
• A Nanocrystal Catalyst Incorporating a Surface Bound Transition Metal to Induce Photocatalytic Sequential Electron Transfer Events
  作者：Jovan San Martin、Xianghua Zeng、Xihan Chen、Collin Miller、Chuang Han、Yixiong Lin、Nobuyuki Yamamoto、Xiaoming Wang、Sadegh Yazdi、Yanfa Yan、Matthew C. Beard、Yong Yan

  DOI：10.1021/jacs.1c00503

  日期：2021.8.4
• Diastereodivergent Synthesis of Bromoiminolactones: Electrochemical and Chemical Bromoiminolactonization of α-Allylmalonamides
  作者：Kosuke Yamamoto、Keiko Ishimaru、Satoshi Mizuta、Daishirou Minato、Masami Kuriyama、Osamu Onomura

  DOI：10.1055/s-0037-1611791

  日期：2019.6

  cis-bromoiminolactones, electrochemical conditions exhibited complementary diastereoselectivity to afford the trans-products. A variety of substituents on the nitrogen atoms and an α-position of the malonamide were tolerated under both sets of conditions to afford the corresponding iminolactones in excellent yields and high diastereoselectivities.

  报道了通过 α-取代的 α-烯丙基丙二酰胺的溴亚氨基内酯化反应非对映异构合成 N-取代的亚氨基内酯。而在常规化学条件下溴环化提供顺式溴亚氨基内酯，电化学条件表现出互补的非对映选择性以提供反式产物。在两组条件下，氮原子上的各种取代基和丙二酰胺的 α 位都可以耐受，从而以优异的产率和高非对映选择性提供相应的亚氨基内酯。