3-Carbomethoxy-5-t-butyldiphenylsilylmethyl tetrahydrofuran-2-one | 362610-89-7

• 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: 3-Carbomethoxy-5-t-butyldiphenylsilylmethyl tetrahydrofuran-2-one
• 英文别名: Methyl 5-[[tert-butyl(diphenyl)silyl]methyl]-2-oxooxolane-3-carboxylate；methyl 5-[[tert-butyl(diphenyl)silyl]methyl]-2-oxooxolane-3-carboxylate
• CAS: 362610-89-7
• 化学式: C₂₃H₂₈O₄Si
• 分子量: 396.558
• InChiKey: VWOPDCJVAFBWPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.15
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-Carbomethoxy-5-t-butyldiphenylsilylmethyl tetrahydrofuran-2-one 在 sodium chloride 作用下， 以 二甲基亚砜 为溶剂， 反应 4.0h， 以85%的产率得到5-[[Tert-butyl(diphenyl)silyl]methyl]oxolan-2-one
  参考文献：
  名称：

  A highly diastereoselective approach to tetrahydrofurans via [3+2] cycloadditions of silylmethyl-substituted cyclopropanes with aldehydes and ketones

  摘要：

  An efficient and highly diastereoselective synthesis of highly substituted tetrahydrofurans from the reaction of a vicinal t-butyldiphenylsilylmethyl-substituted cyclopropyl diester with aldehydes and ketones has been developed. The 2,5-cis-disubstitution predominates over the 2,5-trans-disubstitution by as much as 12:1. The reaction with cyclic ketones generates spiro-fused tetrahydrofurans in good yields. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.09.064
• 作为产物：
  描述：

  dimethyl 2-((tertbutyldiphenylsilyl)methyl)cyclopropane-1,1-dicarboxylate 在 高氯酸 、 四氯化钛 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 8.0h， 生成 3-Carbomethoxy-5-t-butyldiphenylsilylmethyl tetrahydrofuran-2-one
  参考文献：
  名称：

  Silicon-Assisted Ring Opening of Donor−Acceptor Substituted Cyclopropanes. An Expedient Entry to Substituted Dihydrofurans

  摘要：

  [GRAPHICS](tert-Butyldiphenylsilyl)methylcyclopropanes undergo ring opening to furnish substituted dihydrofurans in good to excellent yields on treatment with TiCl4 in dichoromethane. The silicon that assists the regioselective ring opening is retained in the product to allow further functional group manipulations.

  DOI：

  10.1021/ol0163169

文献信息

• A highly diastereoselective approach to tetrahydrofurans via [3+2] cycloadditions of silylmethyl-substituted cyclopropanes with aldehydes and ketones
  作者：Archana Gupta、Veejendra K. Yadav

  DOI：10.1016/j.tetlet.2006.09.064

  日期：2006.11

  An efficient and highly diastereoselective synthesis of highly substituted tetrahydrofurans from the reaction of a vicinal t-butyldiphenylsilylmethyl-substituted cyclopropyl diester with aldehydes and ketones has been developed. The 2,5-cis-disubstitution predominates over the 2,5-trans-disubstitution by as much as 12:1. The reaction with cyclic ketones generates spiro-fused tetrahydrofurans in good yields. (c) 2006 Elsevier Ltd. All rights reserved.
• Silicon-Assisted Ring Opening of Donor−Acceptor Substituted Cyclopropanes. An Expedient Entry to Substituted Dihydrofurans
  作者：Veejendra K. Yadav、Rengarajan Balamurugan

  DOI：10.1021/ol0163169

  日期：2001.8.1

  [GRAPHICS](tert-Butyldiphenylsilyl)methylcyclopropanes undergo ring opening to furnish substituted dihydrofurans in good to excellent yields on treatment with TiCl4 in dichoromethane. The silicon that assists the regioselective ring opening is retained in the product to allow further functional group manipulations.