3,3-bis-(tert-butoxycarbonyl)hexanedioic acid | 819802-92-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3,3-bis-(tert-butoxycarbonyl)hexanedioic acid
• 英文别名: 3,3-Bis[(2-methylpropan-2-yl)oxycarbonyl]hexanedioic acid；3,3-bis[(2-methylpropan-2-yl)oxycarbonyl]hexanedioic acid
• CAS: 819802-92-1
• 化学式: C₁₆H₂₆O₈
• 分子量: 346.378
• InChiKey: RNAXXQXQYCPSKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  24
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  127
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3,3-bis-(tert-butoxycarbonyl)hexanedioic acid 在 potassium tert-butylate 、 caesium carbonate 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙腈 、 叔丁醇 为溶剂， 反应 5.0h， 生成 3-benzyl-1,1-di-tert-butyl (3S,4S)-4-[(1'S)-phenylethylamino]-cyclopentane-1,1,3-tricarboxylate
  参考文献：
  名称：

  Synthesis of 4,4-Disubstituted 2-Aminocyclopentanecarboxylic Acid Derivatives and Their Incorporation into 12-Helical β-Peptides

  摘要：

  An enantioselective synthetic route is reported for trans-2-aminocyclopentanecarboxylic acids (ACPC) bearing geminal side chain pairs at the 4-position. beta-Peptides containing the 4,4-disubstituted ACPC residues adopt the 12-helical conformation, as demonstrated by 2D NMR analysis in aqueous solution. These 4,4-disubstituted ACPC residues display functional groups, including acidic and hydrogen bond donating groups, in a geometrically defined fashion, which should be useful for the design of beta-peptides for specific applications.

  DOI：

  10.1021/ol0483293
• 作为产物：
  描述：

  di-tert-butyl cyclohex-3-ene-1,1-dicarboxylate 在 potassium permanganate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 18.0h， 以60%的产率得到3,3-bis-(tert-butoxycarbonyl)hexanedioic acid
  参考文献：
  名称：

  Synthesis of 4,4-Disubstituted 2-Aminocyclopentanecarboxylic Acid Derivatives and Their Incorporation into 12-Helical β-Peptides

  摘要：

  An enantioselective synthetic route is reported for trans-2-aminocyclopentanecarboxylic acids (ACPC) bearing geminal side chain pairs at the 4-position. beta-Peptides containing the 4,4-disubstituted ACPC residues adopt the 12-helical conformation, as demonstrated by 2D NMR analysis in aqueous solution. These 4,4-disubstituted ACPC residues display functional groups, including acidic and hydrogen bond donating groups, in a geometrically defined fashion, which should be useful for the design of beta-peptides for specific applications.

  DOI：

  10.1021/ol0483293

文献信息

• Synthesis of 4,4-Disubstituted 2-Aminocyclopentanecarboxylic Acid Derivatives and Their Incorporation into 12-Helical β-Peptides
  作者：Timothy J. Peelen、Yonggui Chi、Emily Payne English、Samuel H. Gellman

  DOI：10.1021/ol0483293

  日期：2004.11.1

  An enantioselective synthetic route is reported for trans-2-aminocyclopentanecarboxylic acids (ACPC) bearing geminal side chain pairs at the 4-position. beta-Peptides containing the 4,4-disubstituted ACPC residues adopt the 12-helical conformation, as demonstrated by 2D NMR analysis in aqueous solution. These 4,4-disubstituted ACPC residues display functional groups, including acidic and hydrogen bond donating groups, in a geometrically defined fashion, which should be useful for the design of beta-peptides for specific applications.