ethyl (4S)-4-methyl-2-oxocyclopentane-1-carboxylate | 101694-06-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl (4S)-4-methyl-2-oxocyclopentane-1-carboxylate
• CAS: 101694-06-8
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: FAXGJONUNBBOKH-PKPIPKONSA-N

物化性质

• 沸点：
  237.9±33.0 °C(Predicted)
• 密度：
  1.068±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.16
• 重原子数：
  12.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ethyl (4S)-4-methyl-2-oxocyclopentane-1-carboxylate 在 potassium tert-butylate 、 三氯氧磷 作用下， 以 叔丁醇 为溶剂， 反应 3.0h， 生成 (6S)-4-chloro-2,6-dimethyl-6,7-dihydro-5H-cyclopenta[d]pyrimidine
  参考文献：
  名称：

  Synthesis and Biological Activities of (R)- and (S)-N-(4-Methoxyphenyl)-N,2,6-trimethyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-aminium Chloride as Potent Cytotoxic Antitubulin Agents

  摘要：

  (R,S)-1 is a potent antimitotic compound. (R)-1 center dot HCl and (S)-1 center dot HCl were synthesized from (R)- and (S)-3-methyladipic acid. Both enantiomers were potent inhibitors of cell proliferation and caused cellular microtubule loss and mitotic arrest. They inhibited purified tubulin assembly and the binding of [H-3]colchicine to tubulin, with (S)-1 being about twice as potent. Cytotoxicity against 60 tumor cell lines, however, indicated that the (S)-isomer was 10- to 88-fold more potent than the (R)-isomer.

  DOI：

  10.1021/jm2007722
• 作为产物：
  描述：

  (-)-(S)-3-methylhexanedioic acid 在 硫酸 、 sodium 作用下， 以 甲苯 为溶剂， 反应 11.0h， 生成 ethyl (4S)-4-methyl-2-oxocyclopentane-1-carboxylate
  参考文献：
  名称：

  Synthesis and Biological Activities of (R)- and (S)-N-(4-Methoxyphenyl)-N,2,6-trimethyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-aminium Chloride as Potent Cytotoxic Antitubulin Agents

  摘要：

  (R,S)-1 is a potent antimitotic compound. (R)-1 center dot HCl and (S)-1 center dot HCl were synthesized from (R)- and (S)-3-methyladipic acid. Both enantiomers were potent inhibitors of cell proliferation and caused cellular microtubule loss and mitotic arrest. They inhibited purified tubulin assembly and the binding of [H-3]colchicine to tubulin, with (S)-1 being about twice as potent. Cytotoxicity against 60 tumor cell lines, however, indicated that the (S)-isomer was 10- to 88-fold more potent than the (R)-isomer.

  DOI：

  10.1021/jm2007722