3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yloxy)-N-isobutyl-2,2-dimethyl-propionamide | 464189-11-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yloxy)-N-isobutyl-2,2-dimethyl-propionamide
• CAS: 464189-11-5
• 化学式: C₁₇H₂₂N₂O₄
• 分子量: 318.373
• InChiKey: WPIZGBQHMIWZCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.01
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  75.71
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yloxy)-N-isobutyl-2,2-dimethyl-propionamide 在 一水合肼 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  β^2,2-Aminoxy Acids:  A New Building Block for Turns and Helices

  摘要：

  The conformational properties of peptides 1-4 built from 3-aminoxy-2,2-dimethyl-propionic acid, a beta2,2-aminoxy acid, were investigated by NMR spectroscopy and X-ray crystallography. A novel beta N-O turn involving a nine-membered-ring intramolecular hydrogen bond between NHi+2 and COi was formed in diamides 1 and 2, which was further stabilized by another six-membered-ring intramolecular hydrogen bond between NHi+2 and NOi+1. Triamides 3 and 4 displayed a well-defined helical structure featuring two consecutive beta N-O turns. The X-ray structure of 4 revealed that the amide carbonyl group at position i+2 was twisted +65.9 degrees from that at i position, suggesting a novel 1.79 helix. Therefore, beta2,2-aminoxy acid can be used as a new building block for turns and helices.

  DOI：

  10.1021/ja026966n
• 作为产物：
  描述：

  benzyl 3-((1,3-dioxoisoindolin-2-yl)oxy)-2,2-dimethylpropanoate 在 palladium on activated charcoal N-羟基-7-氮杂苯并三氮唑 、 氢气 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 1.5h， 生成 3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yloxy)-N-isobutyl-2,2-dimethyl-propionamide
  参考文献：
  名称：

  β^2,2-Aminoxy Acids:  A New Building Block for Turns and Helices

  摘要：

  The conformational properties of peptides 1-4 built from 3-aminoxy-2,2-dimethyl-propionic acid, a beta2,2-aminoxy acid, were investigated by NMR spectroscopy and X-ray crystallography. A novel beta N-O turn involving a nine-membered-ring intramolecular hydrogen bond between NHi+2 and COi was formed in diamides 1 and 2, which was further stabilized by another six-membered-ring intramolecular hydrogen bond between NHi+2 and NOi+1. Triamides 3 and 4 displayed a well-defined helical structure featuring two consecutive beta N-O turns. The X-ray structure of 4 revealed that the amide carbonyl group at position i+2 was twisted +65.9 degrees from that at i position, suggesting a novel 1.79 helix. Therefore, beta2,2-aminoxy acid can be used as a new building block for turns and helices.

  DOI：

  10.1021/ja026966n