2-Tert-butyl-2-methyl-6-nitro-1,3-benzodioxole-4-carboxylic acid | 664981-41-3

• 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-Tert-butyl-2-methyl-6-nitro-1,3-benzodioxole-4-carboxylic acid
• CAS: 664981-41-3
• 化学式: C₁₃H₁₅NO₆
• 分子量: 281.265
• InChiKey: NCWDBKMCMCYPET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-Tert-butyl-2-methyl-6-nitro-1,3-benzodioxole-4-carboxylic acid 在 CHIRALPAK AD 、 三氟乙酸 作用下， 以 正己烷 、 异丙醇 为溶剂， 生成 (R)-2-tert-Butyl-2-methyl-6-nitro-benzo[1,3]dioxole-4-carboxylic acid 、 (S)-2-tert-Butyl-2-methyl-6-nitro-benzo[1,3]dioxole-4-carboxylic acid
  参考文献：
  名称：

  Synthesis and characterization of asymmetric o- and m-nitrobenzoic acids with a 1,3-benzodioxole skeleton

  摘要：

  A symmetric o- and m-nitrobenzoic acids with a 1,3-benzodioxole skeleton have been synthesized and characterized. The synthesis involved nitration at either the C-5 or C-6 position of 2-tert-butyl-2-methyl-1,3-benzodioxole-4-carboxylate derived from catechol. These were then resolved with chiral solid-phased HPLC columns into each of enantiomers (>99% ee), which were characterized by circular dichroism. The (S)-enantiomers were also obtained by fractional crystallization of the precursor prior to the nitration. When applied as chiral derivation agents for alcohols and amines, m-nitrobenzoic acid showed notable ability to separate the enantiomers in both HPLC and NMR analyses. On the other hand, H-1 NMR and X-ray data of their ester and amide derivatives strongly suggested that the o-nitrobenzoic acid would serve as a fluorescent building block useful for the assembly of beta-peptide linkages with a defined conformation. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.10.030
• 作为产物：
  描述：

  2-tert-butyl-2-methyl-1,3-benzodioxole-4-carboxylic acid 在 nitronium tetrafluoborate 作用下， 以 乙腈 为溶剂， 生成 2-Tert-butyl-2-methyl-5-nitro-1,3-benzodioxole-4-carboxylic acid 、 2-Tert-butyl-2-methyl-6-nitro-1,3-benzodioxole-4-carboxylic acid
  参考文献：
  名称：

  Synthesis and characterization of asymmetric o- and m-nitrobenzoic acids with a 1,3-benzodioxole skeleton

  摘要：

  A symmetric o- and m-nitrobenzoic acids with a 1,3-benzodioxole skeleton have been synthesized and characterized. The synthesis involved nitration at either the C-5 or C-6 position of 2-tert-butyl-2-methyl-1,3-benzodioxole-4-carboxylate derived from catechol. These were then resolved with chiral solid-phased HPLC columns into each of enantiomers (>99% ee), which were characterized by circular dichroism. The (S)-enantiomers were also obtained by fractional crystallization of the precursor prior to the nitration. When applied as chiral derivation agents for alcohols and amines, m-nitrobenzoic acid showed notable ability to separate the enantiomers in both HPLC and NMR analyses. On the other hand, H-1 NMR and X-ray data of their ester and amide derivatives strongly suggested that the o-nitrobenzoic acid would serve as a fluorescent building block useful for the assembly of beta-peptide linkages with a defined conformation. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.10.030

文献信息

• Synthesis and characterization of asymmetric o- and m-nitrobenzoic acids with a 1,3-benzodioxole skeleton
  作者：Masaya Suzuki、Yoshihiro Nishida、Yuya Ohguro、Yoshiko Miura、Akiko Tsuchida、Kazukiyo Kobayashi

  DOI：10.1016/j.tetasy.2003.10.030

  日期：2004.1

  A symmetric o- and m-nitrobenzoic acids with a 1,3-benzodioxole skeleton have been synthesized and characterized. The synthesis involved nitration at either the C-5 or C-6 position of 2-tert-butyl-2-methyl-1,3-benzodioxole-4-carboxylate derived from catechol. These were then resolved with chiral solid-phased HPLC columns into each of enantiomers (>99% ee), which were characterized by circular dichroism. The (S)-enantiomers were also obtained by fractional crystallization of the precursor prior to the nitration. When applied as chiral derivation agents for alcohols and amines, m-nitrobenzoic acid showed notable ability to separate the enantiomers in both HPLC and NMR analyses. On the other hand, H-1 NMR and X-ray data of their ester and amide derivatives strongly suggested that the o-nitrobenzoic acid would serve as a fluorescent building block useful for the assembly of beta-peptide linkages with a defined conformation. (C) 2003 Elsevier Ltd. All rights reserved.