N,N-diethyl-2-tert-butyl-2-methyl-5-nitro-1,3-benzodioxole-4-carboxamide | 865664-83-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: N,N-diethyl-2-tert-butyl-2-methyl-5-nitro-1,3-benzodioxole-4-carboxamide
• 英文别名: 2-tert-butyl-N,N-diethyl-2-methyl-5-nitro-1,3-benzodioxole-4-carboxamide
• CAS: 865664-83-1
• 化学式: C₁₇H₂₄N₂O₅
• 分子量: 336.388
• InChiKey: JELZKGSYQFRGGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  84.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N,N-diethyl-2-tert-butyl-2-methyl-5-nitro-1,3-benzodioxole-4-carboxamide 、 乙酸酐 在 palladium dihydroxide 氢气 作用下， 以 甲醇 为溶剂， 以95%的产率得到N,N-diethyl-5-acetamido-2-tert-butyl-2-methyl-1,3-benzodioxole-4-carboxamide
  参考文献：
  名称：

  1,3-Benzodioxole-based β- and γ-Peptide Linkages Exhibiting Unique Fluorescence, Conformation, and Self-association Properties

  摘要：

  Four types of beta- and gamma-peptide models were prepared from our previous asymmetric 1,3-benzodioxole and characterized by means of fluorescence and H-1 NMR spectroscopy. A beta-peptide model carrying secondary amide linkages at both of the C- and N-termini took a rigid coplanar conformation, emitting the strongest fluorescence [Ex.(max) 340 nm and Em.(max) 424 nm] among the four models. Dual intra-molecular hydrogen bonds were associated with the stable coplanar conformation. A tertiary beta-peptide model carrying a tertiary amide linkage at the C-terminus took a twisted conformation around the C-terminal to afford a pair of rotational isomers (atropisomers) detectable with H-1 NMR spectroscopy. Both secondary and tertiary gamma-peptide models showed a notable self-association property to afford dimers made of complementary intra- and intermolecular hydrogen bonds.

  DOI：

  10.3987/com-05-10490
• 作为产物：
  描述：

  2-tert-butyl-2-methyl-1,3-benzodioxole-4-carboxylic acid 在 nitronium tetrafluoborate 、 六氟丙烯 、 二乙胺 作用下， 以 甲苯 、 乙腈 为溶剂， 生成 N,N-diethyl-2-tert-butyl-2-methyl-5-nitro-1,3-benzodioxole-4-carboxamide
  参考文献：
  名称：

  1,3-Benzodioxole-based β- and γ-Peptide Linkages Exhibiting Unique Fluorescence, Conformation, and Self-association Properties

  摘要：

  Four types of beta- and gamma-peptide models were prepared from our previous asymmetric 1,3-benzodioxole and characterized by means of fluorescence and H-1 NMR spectroscopy. A beta-peptide model carrying secondary amide linkages at both of the C- and N-termini took a rigid coplanar conformation, emitting the strongest fluorescence [Ex.(max) 340 nm and Em.(max) 424 nm] among the four models. Dual intra-molecular hydrogen bonds were associated with the stable coplanar conformation. A tertiary beta-peptide model carrying a tertiary amide linkage at the C-terminus took a twisted conformation around the C-terminal to afford a pair of rotational isomers (atropisomers) detectable with H-1 NMR spectroscopy. Both secondary and tertiary gamma-peptide models showed a notable self-association property to afford dimers made of complementary intra- and intermolecular hydrogen bonds.

  DOI：

  10.3987/com-05-10490

文献信息

• 1,3-Benzodioxole-based β- and γ-Peptide Linkages Exhibiting Unique Fluorescence, Conformation, and Self-association Properties
  作者：Masaya Suzuki、Yuya Ohguro、Kazukiyo Kobayashi、Yoshihiro Nishida

  DOI：10.3987/com-05-10490

  日期：——

  Four types of beta- and gamma-peptide models were prepared from our previous asymmetric 1,3-benzodioxole and characterized by means of fluorescence and H-1 NMR spectroscopy. A beta-peptide model carrying secondary amide linkages at both of the C- and N-termini took a rigid coplanar conformation, emitting the strongest fluorescence [Ex.(max) 340 nm and Em.(max) 424 nm] among the four models. Dual intra-molecular hydrogen bonds were associated with the stable coplanar conformation. A tertiary beta-peptide model carrying a tertiary amide linkage at the C-terminus took a twisted conformation around the C-terminal to afford a pair of rotational isomers (atropisomers) detectable with H-1 NMR spectroscopy. Both secondary and tertiary gamma-peptide models showed a notable self-association property to afford dimers made of complementary intra- and intermolecular hydrogen bonds.