methyl (2E,4R)-4-{N-(3-bromoprop-2-ynyl)-4-toluenesulfonamido}-5-(tert-butyldimethylsilyloxy)pent-2-enoate | 1232168-42-1

• 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 (2E,4R)-4-{N-(3-bromoprop-2-ynyl)-4-toluenesulfonamido}-5-(tert-butyldimethylsilyloxy)pent-2-enoate
• CAS: 1232168-42-1
• 化学式: C₂₂H₃₂BrNO₅SSi
• 分子量: 530.555
• InChiKey: PAFMSJGJETXJEW-FIIODCPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.46
• 重原子数：
  31.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  72.91
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  methyl (2E,4R)-5-(tert-butyldimethylsilyloxy)-4-{N-(prop-2-ynyl)-4-toluenesulfonamido}pent-2-enoate 在 N-溴代丁二酰亚胺(NBS) 、 silver nitrate 作用下， 以 丙酮 为溶剂， 以99%的产率得到methyl (2E,4R)-4-{N-(3-bromoprop-2-ynyl)-4-toluenesulfonamido}-5-(tert-butyldimethylsilyloxy)pent-2-enoate
  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