ethyl (3R,4S)-3-dimethylphenylsilyl-2-ethoxycarbonyl-4-formyloctanoate | 1262617-14-0

• 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: ethyl (3R,4S)-3-dimethylphenylsilyl-2-ethoxycarbonyl-4-formyloctanoate
• 英文别名: diethyl 2-[(1R,2S)-1-[dimethyl(phenyl)silyl]-2-formylhexyl]propanedioate
• CAS: 1262617-14-0
• 化学式: C₂₂H₃₄O₅Si
• 分子量: 406.594
• InChiKey: RCIZFOFGAXSQSE-FXAWDEMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.72
• 重原子数：
  28
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  ethyl 2-ethoxycarbonyl-3-dimethyl(phenyl)silyl-2-propenoate 、 正己醛 在 (2S)-2-[二苯基[(三甲基硅酯)氧基]甲基]-吡咯烷 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 96.0h， 生成 ethyl (3R,4S)-3-dimethylphenylsilyl-2-ethoxycarbonyl-4-formyloctanoate 、 ethyl 3-dimethylphenylsilyl-2-ethoxycarbonyl-4-formyloctanoate
  参考文献：
  名称：

  醛的有机催化迈克尔加成反应生成β-甲硅烷基丙二酸丙二酸酯，形成中间体，用于对映选择性合成羟基化的戊内酯和哌啶

  摘要：

  （S）-二苯基脯氨醇三甲基甲硅烷基醚/乙酸的组合物催化可烯化醛直接向（甲基）二甲基（苯基）甲硅烷基亚甲基丙二酸酯的迈克尔加成反应。加合物以高收率，高非对映选择性和优异的对映选择性形成。已从加合物中制备了嵌有甲硅烷基和其他官能团的手性戊内酯和哌啶骨架。从一种加合物已经获得了全合成（+）-辛内酯B。

  DOI：

  10.1016/j.tetasy.2010.10.011

文献信息

• Organo-catalyzed enantioselective synthesis of some β-silyl γ-alkyl γ-butyrolactones as intermediates for natural products
  作者：Raghunath Chowdhury、Sunil K. Ghosh

  DOI：10.1016/j.tetasy.2011.10.013

  日期：2011.11

  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.
• Organocatalytic Michael addition of aldehydes to a β-silylmethylene malonate to form intermediates for the enantioselective synthesis of hydroxylated valerolactones and piperidines
  作者：Raghunath Chowdhury、Sunil K. Ghosh

  DOI：10.1016/j.tetasy.2010.10.011

  日期：2010.11

  The direct Michael addition of enolizable aldehydes to dimethyl(phenyl)silylmethylene malonate was catalysed by an (S)-diphenylprolinol trimethylsilyl ether/acetic acid combination. The adducts were formed in good yield, high diastereoselectivity and excellent enantioselectivity. Chiral valerolactone and piperidine skeletons embedded with a silyl and other functionalities have been made out of the

  （S）-二苯基脯氨醇三甲基甲硅烷基醚/乙酸的组合物催化可烯化醛直接向（甲基）二甲基（苯基）甲硅烷基亚甲基丙二酸酯的迈克尔加成反应。加合物以高收率，高非对映选择性和优异的对映选择性形成。已从加合物中制备了嵌有甲硅烷基和其他官能团的手性戊内酯和哌啶骨架。从一种加合物已经获得了全合成（+）-辛内酯B。