cis-(4R)-4-tert-butyldimethylsilyloxy-5-(2-chloromethyl-2-propenyl)-2-pyrrolidone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: cis-(4R)-4-tert-butyldimethylsilyloxy-5-(2-chloromethyl-2-propenyl)-2-pyrrolidone
• 英文别名: (4R,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-[2-(chloromethyl)prop-2-enyl]pyrrolidin-2-one
• 化学式: C₁₄H₂₆ClNO₂Si
• 分子量: 303.904
• InChiKey: LZSVXLUPZAJQSF-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.45
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(氯甲基)烯丙基-三甲基硅烷 、 (4R)-4-tert-butyldimethylsilyloxy-5-methoxy-2-pyrrolidone 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 生成 trans-(4R)-4-tert-butyldimethylsilyloxy-5-(2-chloromethyl-2-propenyl)-2-pyrrolidone 、 cis-(4R)-4-tert-butyldimethylsilyloxy-5-(2-chloromethyl-2-propenyl)-2-pyrrolidone
  参考文献：
  名称：

  Electrochemical oxidation of (R)-4-hydroxy-2-pyrrolidone: A key building block for stereoselective N-acyliminium ion coupling reactions

  摘要：

  The 5-methoxylation of (R)-4-hydroxy-2-pyrrolidone can be performed successfully by direct electrochemical oxidation at 40 mA/cm(2) in methanol at graphite electrodes using an undivided cell and sodium benzene sulfonate as supporting electrolyte. After direct protection of the intermediate as TBDMS ether, (4R)-4-tert-butyldimethylsilyloxy-5-methoxy-2-pyrrolidone 3 can be used in various diastereoselective amidoalkylation reactions. In most cases cis-stereoselectivity is observed. However, the favored cis-addition may be typical only for Si-organic compounds. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00904-7

文献信息

• Electrochemical oxidation of (R)-4-hydroxy-2-pyrrolidone: A key building block for stereoselective N-acyliminium ion coupling reactions
  作者：Michael Lennartz、Masahiro Sadakane、Eberhard Steckhan

  DOI：10.1016/s0040-4020(99)00904-7

  日期：1999.12

  The 5-methoxylation of (R)-4-hydroxy-2-pyrrolidone can be performed successfully by direct electrochemical oxidation at 40 mA/cm(2) in methanol at graphite electrodes using an undivided cell and sodium benzene sulfonate as supporting electrolyte. After direct protection of the intermediate as TBDMS ether, (4R)-4-tert-butyldimethylsilyloxy-5-methoxy-2-pyrrolidone 3 can be used in various diastereoselective amidoalkylation reactions. In most cases cis-stereoselectivity is observed. However, the favored cis-addition may be typical only for Si-organic compounds. (C) 1999 Elsevier Science Ltd. All rights reserved.