(4S,5R)-4-(dimethyl(phenyl)silyl)-5-ethyldihydrofuran-2(3H)-one | 1353637-78-1

• 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-ethyldihydrofuran-2(3H)-one
• 英文别名: (4S,5R)-4-dimethyl(phenyl)silyl-5-ethyl-4,5-dihydrofuran-2(3H)-one；(4S,5R)-4-[dimethyl(phenyl)silyl]-5-ethyloxolan-2-one
• CAS: 1353637-78-1
• 化学式: C₁₄H₂₀O₂Si
• 分子量: 248.397
• InChiKey: QOJSGFPDFFDZRF-OLZOCXBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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-ethyldihydrofuran-2(3H)-one 在 过氧乙酸 、 双氧水 、 溶剂黄146 、 potassium bromide 作用下， 以60%的产率得到(4S,5R)-5-ethyl-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 3-dimethylphenylsilyl-2-ethoxycarbonyl-4-formylhexanoate 在 sodium phosphate dibasic dodecahydrate 、 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 9.0h， 生成 (4S,5R)-4-(dimethyl(phenyl)silyl)-5-ethyldihydrofuran-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

• Stereoselective Synthesis of Polysubstituted Tetrahydropyranones via Acid-Promoted Cyclization of β-Silyl-γ-ethylidene-γ-butyrolactones with Aldehydes and Ketones
  作者：Shoma Ariyoshi、Kazuhiko Sakaguchi、Takahiro Nishimura

  DOI：10.1021/acs.joc.1c01284

  日期：2021.9.3

  β-Silyl-γ-ethylidene-γ-butyrolactone upon one-pot treatment with aldehydes and ketones in the presence of Lewis acids underwent a tandem Hosomi–Sakurai/Prins cyclization to give polysubstituted tetrahydropyranones stereoselectively. Various aldehydes and ketones can be used in this reaction to produce the corresponding tetrahydropyranones. The optical purity of the starting γ-butyrolactone was substantially

  β-甲硅烷基-γ-亚乙基-γ-丁内酯在路易斯酸存在下用醛和酮进行一锅处理后，经过串联的Hosomi-Sakurai/Prins环化反应，立体选择性地得到多取代的四氢吡喃酮。在该反应中可以使用各种醛和酮来生产相应的四氢吡喃酮。起始γ-丁内酯的光学纯度基本上保留在所得四氢吡喃酮中。
• 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.