3-benzyl-1,1-di-tert-butyl 4-oxocyclopentane-1,1,3-tricarboxylate | 819802-99-8

• 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: 3-benzyl-1,1-di-tert-butyl 4-oxocyclopentane-1,1,3-tricarboxylate
• 英文别名: 3-O-benzyl 1-O,1-O'-ditert-butyl 4-oxocyclopentane-1,1,3-tricarboxylate
• CAS: 819802-99-8
• 化学式: C₂₃H₃₀O₇
• 分子量: 418.487
• InChiKey: VYRUOAIJHAKBFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.38
• 重原子数：
  30.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  95.97
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (S)-(-)- α-甲基苄胺 、 3-benzyl-1,1-di-tert-butyl 4-oxocyclopentane-1,1,3-tricarboxylate 在 溶剂黄146 、 sodium cyanoborohydride 作用下， 以 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 、 potassium tert-butylate 、 caesium carbonate 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 18.0h， 生成 3-benzyl-1,1-di-tert-butyl 4-oxocyclopentane-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

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.