ethyl (1R*,2S*,3S*)-3-acetamido-1-cyano-3-methyl-2-(2-oxopropyl)-1-cyclopentanecarboxylate

• 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: ethyl (1R*,2S*,3S*)-3-acetamido-1-cyano-3-methyl-2-(2-oxopropyl)-1-cyclopentanecarboxylate
• 英文别名: ethyl (1S,2R,3R)-3-acetamido-1-cyano-3-methyl-2-(2-oxopropyl)cyclopentane-1-carboxylate
• 化学式: C₁₅H₂₂N₂O₄
• 分子量: 294.351
• InChiKey: HHQALHJNLFVANN-NWANDNLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  96.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  ethyl 2-cyano-5-nitrohexanoate 在 镍 氢气 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 1.0h， 生成 ethyl (1R*,2S*,3S*)-3-acetamido-1-cyano-3-methyl-2-(2-oxopropyl)-1-cyclopentanecarboxylate
  参考文献：
  名称：

  Nitro Compounds in the Double Annulation Route to Trans-Fused Bicyclic Compounds

  摘要：

  Tethered carbon acids bearing nitro groups undergo a double Michael reaction with 3-butyn-2-one, and the cyclic products thereby obtained can be transformed into trans-fused bicyclic compounds with high levels of substitution and functionality. Three new C-C or C-N bonds, two new rings, two to four new stereocenters, and one or two new quaternary centers are created in this novel double annulation of two acyclic, readily available starting materials. Examples of the synthesis of trans-decalins, trans-hydrindanes, and tralzs-perhydroindoles are presented. Methods for converting the nitro groups in the double Michael and double annulation products into other groups are also described.

  DOI：

  10.1021/jo9907888