(2S,3R)-1,1-di(ethoxycarbonyl)-2-dimethyl(phenyl)-silyloctan-3-yl formate | 1353637-84-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2S,3R)-1,1-di(ethoxycarbonyl)-2-dimethyl(phenyl)-silyloctan-3-yl formate
• CAS: 1353637-84-9
• 化学式: C₂₃H₃₆O₆Si
• 分子量: 436.621
• InChiKey: FEILWRKNBPQBTR-TZIWHRDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.84
• 重原子数：
  30.0
• 可旋转键数：
  14.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  78.9
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  庚醛 在 (2S)-2-[二苯基[(三甲基硅酯)氧基]甲基]-吡咯烷 、 sodium phosphate dibasic dodecahydrate 、 溶剂黄146 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 100.0h， 生成 1,1-di(ethoxycarbonyl)-2-dimethyl(phenyl)-silyloctan-3-yl formate 、 (2S,3R)-1,1-di(ethoxycarbonyl)-2-dimethyl(phenyl)-silyloctan-3-yl formate
  参考文献：
  名称：

  Organo-catalyzed enantioselective synthesis of some β-silyl γ-alkyl γ-butyrolactones as intermediates for natural products

  摘要：

  The enantioselective synthesis of some beta-silyl gamma-alkyl gamma-butyrolactones has been achieved by an organo-catalyzed Michael addition of enolizable aldehydes onto a silylmethylene malonate followed by a silicon-facilitated Bayer-Villiger oxidation of the beta-silyl aldehyde adducts as the key step. gamma-Alkyl gamma-butenolides were obtained from the beta-silyl gamma-alkyl gamma-butyrolactones by Fleming-Tamao oxidation of the silyl group to a hydroxy group and subsequent elimination. These butenolides are the advanced intermediates of some natural products such as (+)-gamma-caprolactone, (+)-methylenolactocine, and (-)-quercus lactone. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.10.013