methyl [(2R,3R,4E)-4-(bromomethylene)-2-{(tert-butyldimethylsilyloxy)methyl}-1-(4-toluenesulfonyl)pyrrolidin-3-yl]acetate | 1232168-43-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl [(2R,3R,4E)-4-(bromomethylene)-2-{(tert-butyldimethylsilyloxy)methyl}-1-(4-toluenesulfonyl)pyrrolidin-3-yl]acetate
• 英文别名: methyl 2-[(2R,3R,4E)-4-(bromomethylidene)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-1-(4-methylphenyl)sulfonylpyrrolidin-3-yl]acetate
• CAS: 1232168-43-2
• 化学式: C₂₂H₃₄BrNO₅SSi
• 分子量: 532.571
• InChiKey: NCKMMWQEKRZQBV-FOYATCPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.85
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  81.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  methyl (2E,4R)-4-{N-(3-bromoprop-2-ynyl)-4-toluenesulfonamido}-5-(tert-butyldimethylsilyloxy)pent-2-enoate 在 六甲基磷酰三胺 、 samarium diiodide 、 六氟异丙醇 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 methyl [(2R,3R,4E)-4-(bromomethylene)-2-{(tert-butyldimethylsilyloxy)methyl}-1-(4-toluenesulfonyl)pyrrolidin-3-yl]acetate 、 methyl [(2R,3S,4E)-4-(bromomethylene)-2-{(tert-butyldimethylsilyloxy)methyl}-1-(4-toluenesulfonyl)pyrrolidin-3-yl]acetate
  参考文献：
  名称：

  Diastereoselective Syntheses of Functionalized Five-Membered Carbocycles and Heterocycles by a SmI₂-Promoted Intramolecular Coupling of Bromoalkynes and α,β-Unsaturated Esters

  摘要：

  An intramolecular coupling of bromoalkynes with alpha,beta-unsaturated esters afforded functionalized five-membered carbocycles and heterocycles with high diastereoselectivities in excellent yields. The vinyl bromides newly generated as the products serve as adequate intermediates for further chemical modification.

  DOI：

  10.1021/ol101034s

文献信息

• Diastereoselective Syntheses of Functionalized Five-Membered Carbocycles and Heterocycles by a SmI₂-Promoted Intramolecular Coupling of Bromoalkynes and α,β-Unsaturated Esters
  作者：Kazunori Takahashi、Toshio Honda

  DOI：10.1021/ol101034s

  日期：2010.7.2

  An intramolecular coupling of bromoalkynes with alpha,beta-unsaturated esters afforded functionalized five-membered carbocycles and heterocycles with high diastereoselectivities in excellent yields. The vinyl bromides newly generated as the products serve as adequate intermediates for further chemical modification.