3-Bromo-4-[(S)-2-(1-methoxy-1-methyl-ethyl)-pyrrolidin-1-yl]-5H-furan-2-one | 157161-41-6

• 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: 3-Bromo-4-[(S)-2-(1-methoxy-1-methyl-ethyl)-pyrrolidin-1-yl]-5H-furan-2-one
• 英文别名: 4-bromo-3-[(2S)-2-(2-methoxypropan-2-yl)pyrrolidin-1-yl]-2H-furan-5-one
• CAS: 157161-41-6
• 化学式: C₁₂H₁₈BrNO₃
• 分子量: 304.184
• InChiKey: WSXOBTAADTVURO-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  3-Bromo-4-[(S)-2-(1-methoxy-1-methyl-ethyl)-pyrrolidin-1-yl]-5H-furan-2-one 在 双(三甲基硅烷基)氨基钾 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 3.33h， 生成 (S)-1-(4-Bromo-2-methyl-5-triisopropylsilanyloxy-furan-3-yl)-2-(1-methoxy-1-methyl-ethyl)-pyrrolidine
  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 作用下， 以 乙腈 、 叔丁醇 为溶剂， 生成 3-Bromo-4-[(S)-2-(1-methoxy-1-methyl-ethyl)-pyrrolidin-1-yl]-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 of nonracemic 3- and 4-amino furans bound to polystyrene. A comparison of these reactions to their solution state analogues
  作者：Richard H. Schlessinger、Carl P. Bergstrom

  DOI：10.1016/0040-4039(96)00208-0

  日期：1996.3

  The potassium enolates of the 3 and 4-amino furanones 4 and 12 have been silylated with polymer 3. The resulting polymer-bound nonracemic amino furans 5 and 11 were found to undergo the Diels-Alder reaction with a variety of dienophiles. The endo-adducts derived from methyl acrylate were both directly cleaved from the polymer and or synthetically manipulated and then cleaved from the polymer to demonstrate

  3和4-氨基呋喃酮4和12的烯醇钾已经被聚合物3甲硅烷基化。发现与聚合物结合的非外消旋氨基呋喃5和11与多种亲双烯体进行狄尔斯-阿尔德反应。衍生自丙烯酸甲酯的内加合物既可以直接从聚合物上裂解，也可以进行合成操作，然后再从聚合物上裂解，以证明它们在> 99％de中的形成。
• Enantioselective Synthesis of (+)-Cyclophellitol
  作者：Richard H. Schlessinger、Carl P. Bergstrom

  DOI：10.1021/jo00106a008

  日期：1995.1
• 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.