(S)-3-Bromo-4-[(S)-2-(1-methoxy-1-methyl-ethyl)-pyrrolidin-1-yl]-5-methyl-5H-furan-2-one | 157161-42-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: (S)-3-Bromo-4-[(S)-2-(1-methoxy-1-methyl-ethyl)-pyrrolidin-1-yl]-5-methyl-5H-furan-2-one
• 英文别名: (2S)-4-bromo-3-[(2S)-2-(2-methoxypropan-2-yl)pyrrolidin-1-yl]-2-methyl-2H-furan-5-one
• CAS: 157161-42-7
• 化学式: C₁₃H₂₀BrNO₃
• 分子量: 318.211
• InChiKey: DWABDVVEFOWZQP-IUCAKERBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-3-Bromo-4-[(S)-2-(1-methoxy-1-methyl-ethyl)-pyrrolidin-1-yl]-5-methyl-5H-furan-2-one 在 四丁基氟化铵 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 为溶剂， 反应 3.33h， 生成 (S)-2-{(S)-4-Bromo-3-[(S)-2-(1-methoxy-1-methyl-ethyl)-pyrrolidin-1-yl]-2-methyl-5-oxo-2,5-dihydro-furan-2-yl}-succinic acid dimethyl ester
  参考文献：
  名称：

  Diastereoselective Diels-Alder Reactions Using Furan Substituted with a Nonracemic Amine

  摘要：

  The furan derivative 1 undergoes diastereoselective Diels-Alder reactions with dienophilic species such as alpha,beta-unsaturated esters, nitriles, sulfones, and imides in good to excellent chemical yields. The oxobicyclic adducts obtained are amenable to chemical transformations which render them useful to natural product synthesis.

  DOI：

  10.1021/jo00091a002
• 作为产物：
  描述：

  (2S)-(2-甲氧基丙基-2-基)吡咯烷 在 N-溴代丁二酰亚胺(NBS) 、 四丁基氟化铵 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙腈 、 叔丁醇 为溶剂， 生成 (S)-3-Bromo-4-[(S)-2-(1-methoxy-1-methyl-ethyl)-pyrrolidin-1-yl]-5-methyl-5H-furan-2-one
  参考文献：
  名称：

  Diastereoselective Diels-Alder Reactions Using Furan Substituted with a Nonracemic Amine

  摘要：

  The furan derivative 1 undergoes diastereoselective Diels-Alder reactions with dienophilic species such as alpha,beta-unsaturated esters, nitriles, sulfones, and imides in good to excellent chemical yields. The oxobicyclic adducts obtained are amenable to chemical transformations which render them useful to natural product synthesis.

  DOI：

  10.1021/jo00091a002

文献信息

• Diastereoselective Diels-Alder Reactions Using Furan Substituted with a Nonracemic Amine
  作者：Richard H. Schlessinger、Thomas R. R. Pettus、James P. Springer、Karst Hoogsteen

  DOI：10.1021/jo00091a002

  日期：1994.6

  The furan derivative 1 undergoes diastereoselective Diels-Alder reactions with dienophilic species such as alpha,beta-unsaturated esters, nitriles, sulfones, and imides in good to excellent chemical yields. The oxobicyclic adducts obtained are amenable to chemical transformations which render them useful to natural product synthesis.