(4S,5R)-4-dimethyl(phenyl)silyl-5-butyl-4,5-dihydrofuran-2(3H)-one | 1353637-80-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (4S,5R)-4-dimethyl(phenyl)silyl-5-butyl-4,5-dihydrofuran-2(3H)-one
• 英文别名: (4S,5R)-5-butyl-4-(dimethyl(phenyl)silyl)dihydrofuran-2(3H)-one；(4S,5R)-5-butyl-4-[dimethyl(phenyl)silyl]oxolan-2-one
• CAS: 1353637-80-5
• 化学式: C₁₆H₂₄O₂Si
• 分子量: 276.451
• InChiKey: TZEORJLTZRLVNU-CABCVRRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.48
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4S,5R)-4-dimethyl(phenyl)silyl-5-butyl-4,5-dihydrofuran-2(3H)-one 在 过氧乙酸 、 双氧水 、 溶剂黄146 、 potassium bromide 作用下， 以58%的产率得到(4S,5R)-5-butyl-4-hydroxy-4,5-dihydrofuran-2(3H)-one
  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
• 作为产物：
  描述：

  ethyl 2-ethoxycarbonyl-3-dimethyl(phenyl)silyl-2-propenoate 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 、 potassium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 105.0h， 生成 (4S,5R)-4-dimethyl(phenyl)silyl-5-butyl-4,5-dihydrofuran-2(3H)-one 、 4-dimethyl(phenyl)silyl-5-butyl-4,5-dihydrofuran-2(3H)-one
  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

文献信息

• NHC–Cu(i) catalysed asymmetric conjugate silyl transfer to unsaturated lactones: application in kinetic resolution
  作者：Vittorio Pace、James P. Rae、Hassan Y. Harb、David J. Procter

  DOI：10.1039/c3cc42160k

  日期：——

  The scope of the asymmetric silyl transfer to unsaturated lactones utilising a C2-symmetric NHC–Cu(I) catalyst has been established and kinetic resolutions mediated by silyl transfer have been used to prepare enantiomerically enriched anti-4,5-disubstituted 5-membered lactones. The method has been exploited in an expedient synthesis of (+)-blastmycinone.

  利用 C2 对称 NHCâCu(I) 催化剂对不饱和内酯进行不对称硅基转移的范围已经确定，并利用硅基转移介导的动力学解析制备了对映体富集的反 4,5 二取代 5 元内酯。该方法已被用于 (+)-blastmycinone 的快速合成。
• 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.