N-(2,5-dihydroxyphenyl)-N-phenylacetamide | 1000622-41-2

• 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: N-(2,5-dihydroxyphenyl)-N-phenylacetamide
• CAS: 1000622-41-2
• 化学式: C₁₄H₁₃NO₃
• 分子量: 243.262
• InChiKey: VNDGZDXMWSEKNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  60.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2,5-dihydroxyphenyl)-N-phenylacetamide 在 盐酸 、 iron(III) chloride 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 以70%的产率得到N-(3,6-dioxocyclohexa-1,4-dien-1-yl)-N-phenylacetamide
  参考文献：
  名称：

  Redox-responsive conformational alteration of aromatic amides bearing N-quinonyl system

  摘要：

  Redox-induced conformational alteration of N-aryl-N-phenylamides, in which the N-aryl group consists of a hydroquinone-p-quinone system, was examined. The reduced form bearing a dihydroxyphenyl or dimethoxyphenyl group exists mainly in the E-form, whereas the oxidized form bearing a N-benzoquinone moiety takes the Z-form both in the crystal and in solution. This redox-induced conformational alteration is associated with a marked change in optical properties. This system appears to have suitable properties for use in external redox stimulus-responsive functional switching. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.04.114
• 作为产物：
  描述：

  2,5-二甲氧基苯胺 在 三叔丁基膦 、 三溴化硼 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 、 sodium t-butanolate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 57.08h， 生成 N-(2,5-dihydroxyphenyl)-N-phenylacetamide
  参考文献：
  名称：

  Redox-responsive conformational alteration of aromatic amides bearing N-quinonyl system

  摘要：

  Redox-induced conformational alteration of N-aryl-N-phenylamides, in which the N-aryl group consists of a hydroquinone-p-quinone system, was examined. The reduced form bearing a dihydroxyphenyl or dimethoxyphenyl group exists mainly in the E-form, whereas the oxidized form bearing a N-benzoquinone moiety takes the Z-form both in the crystal and in solution. This redox-induced conformational alteration is associated with a marked change in optical properties. This system appears to have suitable properties for use in external redox stimulus-responsive functional switching. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.04.114

文献信息

• Redox-Induced Conformational Alteration of <i>N</i>,<i>N</i>-Diarylamides
  作者：Iwao Okamoto、Ryu Yamasaki、Mika Sawamura、Takako Kato、Naomi Nagayama、Tetsuya Takeya、Osamu Tamura、Hyuma Masu、Isao Azumaya、Kentaro Yamaguchi、Hiroyuki Kagechika、Aya Tanatani

  DOI：10.1021/ol702504x

  日期：2007.12.1

  We constructed a novel molecular conformational alteration system with an N-aryl-N-phenylacetamide structure, in which the N-aryl group consists of a hydroquinone-p-quinone system as a redox-dependent aromatic trigger. The amide conformation depended on-the oxidation state of the aryl group, and the two states (compounds 2 and 3) were reversibly converted to each other by redox reactions. Such compounds would be applied as useful structural units for external stimulus-responsive control on the shape and function of large molecules or supramolecules.
• Redox-responsive conformational alteration of aromatic amides bearing N-quinonyl system
  作者：Iwao Okamoto、Yusuke Takahashi、Mika Sawamura、Mio Matsumura、Hyuma Masu、Kosuke Katagiri、Isao Azumaya、Masanori Nishino、Yukari Kohama、Nobuyoshi Morita、Osamu Tamura、Hiroyuki Kagechika、Aya Tanatani

  DOI：10.1016/j.tet.2012.04.114

  日期：2012.7

  Redox-induced conformational alteration of N-aryl-N-phenylamides, in which the N-aryl group consists of a hydroquinone-p-quinone system, was examined. The reduced form bearing a dihydroxyphenyl or dimethoxyphenyl group exists mainly in the E-form, whereas the oxidized form bearing a N-benzoquinone moiety takes the Z-form both in the crystal and in solution. This redox-induced conformational alteration is associated with a marked change in optical properties. This system appears to have suitable properties for use in external redox stimulus-responsive functional switching. (c) 2012 Elsevier Ltd. All rights reserved.