methyl 4,4-bis-(tert-butoxymethyl)-2-oxocyclopentanecarboxylate | 819803-00-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4,4-bis-(tert-butoxymethyl)-2-oxocyclopentanecarboxylate
• CAS: 819803-00-4
• 化学式: C₁₇H₃₀O₅
• 分子量: 314.422
• InChiKey: CCYOOBHBTJPYTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.76
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl 4,4-bis-(tert-butoxymethyl)-2-oxocyclopentanecarboxylate 在 lithium hydroxide 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 水 、 叔丁醇 为溶剂， 反应 51.0h， 生成 (1S,2S)-4,4-Bis-tert-butoxymethyl-2-((S)-1-phenyl-ethylamino)-cyclopentanecarboxylic 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
• 作为产物：
  描述：

  3,3-bis-(tert-butoxymethyl)-hexanedioic acid 在 potassium tert-butylate 、 potassium hydrogencarbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 methyl 4,4-bis-(tert-butoxymethyl)-2-oxocyclopentanecarboxylate
  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