(1S,2S,4S)-6-Bromo-5-[(S)-2-(1-methoxy-1-methyl-ethyl)-pyrrolidin-1-yl]-4-methyl-1-triisopropylsilanyloxy-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester | 157161-43-8

• 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: (1S,2S,4S)-6-Bromo-5-[(S)-2-(1-methoxy-1-methyl-ethyl)-pyrrolidin-1-yl]-4-methyl-1-triisopropylsilanyloxy-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester
• 英文别名: methyl (1S,2S,4S)-6-bromo-5-[(2S)-2-(2-methoxypropan-2-yl)pyrrolidin-1-yl]-4-methyl-1-tri(propan-2-yl)silyloxy-7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylate
• CAS: 157161-43-8
• 化学式: C₂₆H₄₆BrNO₅Si
• 分子量: 560.644
• InChiKey: YUJBDIGZQYOARN-RWVXUKFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.35
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1S,2S,4S)-6-Bromo-5-[(S)-2-(1-methoxy-1-methyl-ethyl)-pyrrolidin-1-yl]-4-methyl-1-triisopropylsilanyloxy-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以90%的产率得到3-{(S)-4-Bromo-3-[(S)-2-(1-methoxy-1-methyl-ethyl)-pyrrolidin-1-yl]-2-methyl-5-oxo-2,5-dihydro-furan-2-yl}-propionic acid methyl 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：

  丙烯酸甲酯（MA） 、 (S)-1-(4-Bromo-2-methyl-5-triisopropylsilanyloxy-furan-3-yl)-2-(1-methoxy-1-methyl-ethyl)-pyrrolidine 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 (1S,2S,4S)-6-Bromo-5-[(S)-2-(1-methoxy-1-methyl-ethyl)-pyrrolidin-1-yl]-4-methyl-1-triisopropylsilanyloxy-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester 、 (1S,2R,4S)-6-Bromo-5-[(S)-2-(1-methoxy-1-methyl-ethyl)-pyrrolidin-1-yl]-4-methyl-1-triisopropylsilanyloxy-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl 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

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.