4-phenylbut-3-yn-2-yl 2-chloroacetate | 726202-33-1

• 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: 4-phenylbut-3-yn-2-yl 2-chloroacetate
• CAS: 726202-33-1
• 化学式: C₁₂H₁₁ClO₂
• 分子量: 222.671
• InChiKey: TVQDCSCCUDGZDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-phenylbut-3-yn-2-yl 2-chloroacetate 在 sodium azide 作用下， 以 水 、 丙酮 为溶剂， 反应 2.0h， 以92%的产率得到4-phenylbut-3-yn-2-yl 2-azidoacetate
  参考文献：
  名称：

  Site-Selective α-Alkoxyl Alkynation of Alkyl Esters Mediated by Boryl Radicals

  摘要：

  A novel method for site-selective C-H functionalization of ethyl acetate mediated by pyridine boryl radicals is presented, delivering a variety of 4-phenylbut-3-yn-2-yl acetate derivatives under mild conditions. A distinguishing feature of this reaction is that the pyridine-ligated boryl radicals can abstract the inactive a-hydrogen of the alkoxyl group instead of the a-hydrogen of carbonyl groups described in a previous report using amine-ligated boryl radicals. Significantly, substrates with halogen atoms are compatible under the reaction conditions.

  DOI：

  10.1021/acs.orglett.9b00985
• 作为产物：
  描述：

  2-(苯磺酰基)乙炔基苯 、 氯乙酸乙酯 在 4-氰基吡啶 、 4-氰基吡啶 N-氧化物 、 联硼酸新戊二醇酯 作用下， 反应 0.5h， 以65%的产率得到4-phenylbut-3-yn-2-yl 2-chloroacetate
  参考文献：
  名称：

  Site-Selective α-Alkoxyl Alkynation of Alkyl Esters Mediated by Boryl Radicals

  摘要：

  A novel method for site-selective C-H functionalization of ethyl acetate mediated by pyridine boryl radicals is presented, delivering a variety of 4-phenylbut-3-yn-2-yl acetate derivatives under mild conditions. A distinguishing feature of this reaction is that the pyridine-ligated boryl radicals can abstract the inactive a-hydrogen of the alkoxyl group instead of the a-hydrogen of carbonyl groups described in a previous report using amine-ligated boryl radicals. Significantly, substrates with halogen atoms are compatible under the reaction conditions.

  DOI：

  10.1021/acs.orglett.9b00985

文献信息

• Schwier, Todd; Rubin, Michael; Gevorgyan, Vladimir, Organic letters, 2004, vol. 6, # 12, p. 1999 - 2001
  作者：Schwier, Todd、Rubin, Michael、Gevorgyan, Vladimir

  DOI：——

  日期：——
• Site-Selective α-Alkoxyl Alkynation of Alkyl Esters Mediated by Boryl Radicals
  作者：Ao Guo、Jia-Bin Han、Lei Zhu、Yin Wei、Xiang-Ying Tang

  DOI：10.1021/acs.orglett.9b00985

  日期：2019.4.19

  A novel method for site-selective C-H functionalization of ethyl acetate mediated by pyridine boryl radicals is presented, delivering a variety of 4-phenylbut-3-yn-2-yl acetate derivatives under mild conditions. A distinguishing feature of this reaction is that the pyridine-ligated boryl radicals can abstract the inactive a-hydrogen of the alkoxyl group instead of the a-hydrogen of carbonyl groups described in a previous report using amine-ligated boryl radicals. Significantly, substrates with halogen atoms are compatible under the reaction conditions.