(1R,2R,5S)-2-((S)-1-Dimethylcarbamoyl-ethyl)-5-methyl-cyclopentanecarboxylic acid methyl ester | 142529-05-3

• 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: (1R,2R,5S)-2-((S)-1-Dimethylcarbamoyl-ethyl)-5-methyl-cyclopentanecarboxylic acid methyl ester
• CAS: 142529-05-3
• 化学式: C₁₃H₂₃NO₃
• 分子量: 241.331
• InChiKey: KILIGNAKKAIOIA-UKKRHICBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.55
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1R,2R,5S)-2-((S)-1-Dimethylcarbamoyl-ethyl)-5-methyl-cyclopentanecarboxylic acid methyl ester 在 锂硼氢 作用下， 以 四氢呋喃 为溶剂， 以58%的产率得到(S)-2-((1S,2R,3S)-2-Hydroxymethyl-3-methyl-cyclopentyl)-N,N-dimethyl-propionamide
  参考文献：
  名称：

  Doubly allylic strain - controlled diastereoselective intramolecular michael addition and a synthesis of (±)-iridomyrmecin in two steps.

  摘要：

  Diastereoselective construction of four contiguous asymmetric centers assembled in a trisubstituted cyclopentane ring has been achieved via a doubly A(1,3)-strain - controlled intramolecular Michael addition, and the resulting compound has been converted into (+/-)-iridomyrmecin in two steps.

  DOI：

  10.1016/s0040-4039(00)78869-1
• 作为产物：
  描述：

  (E)-7-Dimethylcarbamoyl-3-methyl-oct-6-enoic acid methyl ester 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以68%的产率得到(1R,2R,5S)-2-((S)-1-Dimethylcarbamoyl-ethyl)-5-methyl-cyclopentanecarboxylic acid methyl ester
  参考文献：
  名称：

  Doubly allylic strain - controlled diastereoselective intramolecular michael addition and a synthesis of (±)-iridomyrmecin in two steps.

  摘要：

  Diastereoselective construction of four contiguous asymmetric centers assembled in a trisubstituted cyclopentane ring has been achieved via a doubly A(1,3)-strain - controlled intramolecular Michael addition, and the resulting compound has been converted into (+/-)-iridomyrmecin in two steps.

  DOI：

  10.1016/s0040-4039(00)78869-1