(2R,2S)-4-(tert-butyldimethylsilyl)oxymethyl-2-methyl-2-(pent-3-ynyl)-γ-butyrolactone | 1048341-64-5

• 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: (2R,2S)-4-(tert-butyldimethylsilyl)oxymethyl-2-methyl-2-(pent-3-ynyl)-γ-butyrolactone
• 英文别名: (3R,5S)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-methyl-3-pent-3-ynyloxolan-2-one
• CAS: 1048341-64-5
• 化学式: C₁₇H₃₀O₃Si
• 分子量: 310.509
• InChiKey: NFTRIJBEAMDNFW-WMLDXEAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.13
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,2S)-4-(tert-butyldimethylsilyl)oxymethyl-2-methyl-2-(pent-3-ynyl)-γ-butyrolactone 在 二异丁基氢化铝 、 ammonium chloride 作用下， 以 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 1.0h， 以92%的产率得到(2R,4S)-4-(tert-butyldimethylsilyl)oxymethyl-2-methyl-2-(pent-3-ynyl)-γ-butyrolactol
  参考文献：
  名称：

  A Synthetic Approach to the Fusicoccane A−B Ring Fragment Based on a Pauson−Khand Cycloaddition/Norrish Type 1 Fragmentation

  摘要：

  A synthetic approach to the A-B ring system within the fusicoccane family of diterpenes is presented. Key steps in this approach are a diastereoselective Pauson-Khand reaction, a Norrish 1 photofragmentation, a Charette cyclopropanation, and a ring-closing metathesis process.

  DOI：

  10.1021/jo800933f
• 作为产物：
  描述：

  (4S)-4-(tert-butyldimethylsilyl)oxymethyl-2-methyl-γ-butyrolactone 、 5-iodopent-2-yne 在 六甲基磷酰三胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.75h， 以43%的产率得到(2R,2S)-4-(tert-butyldimethylsilyl)oxymethyl-2-methyl-2-(pent-3-ynyl)-γ-butyrolactone
  参考文献：
  名称：

  A Synthetic Approach to the Fusicoccane A−B Ring Fragment Based on a Pauson−Khand Cycloaddition/Norrish Type 1 Fragmentation

  摘要：

  A synthetic approach to the A-B ring system within the fusicoccane family of diterpenes is presented. Key steps in this approach are a diastereoselective Pauson-Khand reaction, a Norrish 1 photofragmentation, a Charette cyclopropanation, and a ring-closing metathesis process.

  DOI：

  10.1021/jo800933f

文献信息

• A Synthetic Approach to the Fusicoccane A−B Ring Fragment Based on a Pauson−Khand Cycloaddition/Norrish Type 1 Fragmentation
  作者：Gregory R. Dake、Erik E. Fenster、Brian O. Patrick

  DOI：10.1021/jo800933f

  日期：2008.9.1

  A synthetic approach to the A-B ring system within the fusicoccane family of diterpenes is presented. Key steps in this approach are a diastereoselective Pauson-Khand reaction, a Norrish 1 photofragmentation, a Charette cyclopropanation, and a ring-closing metathesis process.