4,4-bis-(tert-butoxymethyl)-cyclohexene | 819802-93-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,4-bis-(tert-butoxymethyl)-cyclohexene
• 英文别名: 4,4-Bis(tert-butoxymethyl)cyclohex-1-ene；4,4-bis[(2-methylpropan-2-yl)oxymethyl]cyclohexene
• CAS: 819802-93-2
• 化学式: C₁₆H₃₀O₂
• 分子量: 254.413
• InChiKey: HRKWXKAHPAHLES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,4-bis-(tert-butoxymethyl)-cyclohexene 在 palladium on activated charcoal lithium hydroxide 、 potassium permanganate 、 potassium tert-butylate 、 ammonium formate 、 碳酸氢钠 、 potassium hydrogencarbonate 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 叔丁醇 为溶剂， 反应 78.0h， 生成 4,4-bis-(tert-butoxymethyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)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：

  cyclohex-3-ene-1,1-dicarboxylic acid diethyl ester 在 lithium aluminium tetrahydride 、 硫酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 4,4-bis-(tert-butoxymethyl)-cyclohexene
  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.