ethyl (4E)-{4-(bromomethylene)-1-(4-toluenesulfonyl)pyrrolidin-3-yl}acetate | 1232167-90-6

• 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: ethyl (4E)-{4-(bromomethylene)-1-(4-toluenesulfonyl)pyrrolidin-3-yl}acetate
• 英文别名: ethyl 2-[(4E)-4-(bromomethylidene)-1-(4-methylphenyl)sulfonylpyrrolidin-3-yl]acetate
• CAS: 1232167-90-6
• 化学式: C₁₆H₂₀BrNO₄S
• 分子量: 402.309
• InChiKey: FOGKBFBMDQYMLK-ZROIWOOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl (4E)-{4-(bromomethylene)-1-(4-toluenesulfonyl)pyrrolidin-3-yl}acetate 、 methylzinc chloride 在 palladium diacetate 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醚 、 甲苯 为溶剂， 反应 5.0h， 以93%的产率得到ethyl (4E)-{4-ethylidene-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：

  ethyl (2E)-4-{N-(3-bromoprop-2-ynyl)-4-toluenesulfonamido}but-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， 以90%的产率得到ethyl (4E)-{4-(bromomethylene)-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.