3-(2-Cyano-ethyl)-4-oxo-nonanoic acid methyl ester | 128893-61-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: 3-(2-Cyano-ethyl)-4-oxo-nonanoic acid methyl ester
• 英文别名: Methyl 3-(2-cyanoethyl)-4-oxononanoate
• CAS: 128893-61-8
• 化学式: C₁₃H₂₁NO₃
• 分子量: 239.315
• InChiKey: LWRZZGCEYXFTDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  67.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(2-Cyano-ethyl)-4-oxo-nonanoic acid methyl ester 生成 2-戊基环戊酮-3-乙酸甲酯
  参考文献：
  名称：

  SHONO, TATSUYA;KISE, NAOKI, TETRAHEDRON LETT., 31,(1990) N, C. 1303-1306

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(2-Cyano-ethyl)-2-hexanoyl-succinic acid 1-tert-butyl ester 4-methyl ester 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 生成 3-(2-Cyano-ethyl)-4-oxo-nonanoic acid methyl ester
  参考文献：
  名称：

  Electroorganic chemistry. 140. Electroreductively promoted intra- and intermolecular couplings of ketones with nitriles.

  摘要：

  Electroreduction of gamma and delta-cyano ketones in i-PrOH with Sn cathode gave alpha-hydroxy ketones and their dehydroxylated ketones as the intramolecularly coupled products. Guaiazulene, (-)-valeranone, polyquinanes, dihydrojasmone, methyl dihydrojasmonate, and rosaprostol have been synthesized by utilizing this electroreductive intramolecular coupling of gamma and delta-cyano ketones in one of the key steps. Similarly, electroreduction of a mixture of ketone and nitrile gave the corresponding intermolecularly coupled product. The product obtained by the electroreductive intermolecular coupling of (+)-dihydrocarvone with acetonitrile has been found to be the precursor of an effective chiral ligand for the enantioselective addition of diethylzinc to aldehydes.

  DOI：

  10.1021/jo00052a036

文献信息

• Electroreductive intramolecular coupling of γ- and δ-cyanoketones
  作者：Tatsuya Shono、Naoki Kise

  DOI：10.1016/s0040-4039(00)88791-2

  日期：1990.1

  Electroreduction of γ- and δ-cyanoketones in i-PrOH gave cyclized products α-hydroxyketones and their dehydroxylated ketones, and this reaction was applied to the synthesis of dihydrojasmone, methyl dihydrojasmonate, and Rosaprostol.

  在i-PrOH中电还原γ-和δ-氰基酮，生成环化产物α-羟基酮及其脱羟基酮，并将该反应用于二氢茉莉酮，二氢茉莉酮酸甲酯和Rosaprostol的合成。
• SHONO, TATSUYA;KISE, NAOKI, TETRAHEDRON LETT., 31,(1990) N, C. 1303-1306
  作者：SHONO, TATSUYA、KISE, NAOKI

  DOI：——

  日期：——
• Electroorganic chemistry. 140. Electroreductively promoted intra- and intermolecular couplings of ketones with nitriles.
  作者：Tatsuya Shono、Naoki Kise、Taku Fujimoto、Naoto Tominaga、Hiroshi Morita

  DOI：10.1021/jo00052a036

  日期：1992.12

  Electroreduction of gamma and delta-cyano ketones in i-PrOH with Sn cathode gave alpha-hydroxy ketones and their dehydroxylated ketones as the intramolecularly coupled products. Guaiazulene, (-)-valeranone, polyquinanes, dihydrojasmone, methyl dihydrojasmonate, and rosaprostol have been synthesized by utilizing this electroreductive intramolecular coupling of gamma and delta-cyano ketones in one of the key steps. Similarly, electroreduction of a mixture of ketone and nitrile gave the corresponding intermolecularly coupled product. The product obtained by the electroreductive intermolecular coupling of (+)-dihydrocarvone with acetonitrile has been found to be the precursor of an effective chiral ligand for the enantioselective addition of diethylzinc to aldehydes.