(1S,2R)-3,3-dimethyl-2-(2-oxo-ethyl)-cyclohexanecarboxylic acid methyl ester | 711028-86-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2R)-3,3-dimethyl-2-(2-oxo-ethyl)-cyclohexanecarboxylic acid methyl ester
• 英文别名: methyl (1S,2R)-3,3-dimethyl-2-(2-oxoethyl)cyclohexane-1-carboxylate
• CAS: 711028-86-3
• 化学式: C₁₂H₂₀O₃
• 分子量: 212.289
• InChiKey: ZYAWHINNQXKUET-VHSXEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,2R)-3,3-dimethyl-2-(2-oxo-ethyl)-cyclohexanecarboxylic acid methyl ester 在 盐酸 、 仲丁基锂 作用下， 以 乙醚 、 环己烷 为溶剂， 反应 3.0h， 生成 Ricciocarpin B
  参考文献：
  名称：

  Application of Enantioselective Radical Reactions:  Synthesis of (+)-Ricciocarpins A and B

  摘要：

  Enantioselective synthesis of (+)-ricciocarpins A and B has been achieved in 41 and 45% overall yields, respectively, starting from a beta-substituted oxazolidinone. The key steps in the strategy are an enantioselective conjugate radical addition and the addition of a furyl organometallic to a key aldehyde intermediate.

  DOI：

  10.1021/ol0495772
• 作为产物：
  描述：

  3-[3-(2-benzyloxy-ethyl)-7-chloro-4,4-dimethyl-heptanoyl]-oxazolidin-2-one 在 palladium dihydroxide 、 碳酸氢钠 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 氢气 、 sodium iodide 、 potassium bromide 、 lithium hexamethyldisilazane 、 samarium(III) trifluoromethanesulfonate 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 乙酸乙酯 、 丙酮 为溶剂， 反应 80.5h， 生成 (1S,2R)-3,3-dimethyl-2-(2-oxo-ethyl)-cyclohexanecarboxylic acid methyl ester
  参考文献：
  名称：

  Application of Enantioselective Radical Reactions:  Synthesis of (+)-Ricciocarpins A and B

  摘要：

  Enantioselective synthesis of (+)-ricciocarpins A and B has been achieved in 41 and 45% overall yields, respectively, starting from a beta-substituted oxazolidinone. The key steps in the strategy are an enantioselective conjugate radical addition and the addition of a furyl organometallic to a key aldehyde intermediate.

  DOI：

  10.1021/ol0495772

文献信息

• A Short Synthesis of (±)-Ricciocarpin A UsingIntramolecular Reductive Michael Reaction
  作者：Kei Takeda、Naoki Ohkawa、Kozo Hori、Toru Koizumi、Eiichi Yoshii

  DOI：10.3987/com-97-s(n)13

  日期：——

  A synthesis of furanosesquiterpene ricciocarpin A (3), featuring the efficient construction of the cyclohexane framework by intramolecular reductive annulation using L-Selectride(R), is described.
• Application of Enantioselective Radical Reactions:  Synthesis of (+)-Ricciocarpins A and B
  作者：Mukund P. Sibi、Liwen He

  DOI：10.1021/ol0495772

  日期：2004.5.1

  Enantioselective synthesis of (+)-ricciocarpins A and B has been achieved in 41 and 45% overall yields, respectively, starting from a beta-substituted oxazolidinone. The key steps in the strategy are an enantioselective conjugate radical addition and the addition of a furyl organometallic to a key aldehyde intermediate.