3-[(pentafluorophenyl)(pentafluorophenylamino)methyl]but-3-en-2-one | 851867-22-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-[(pentafluorophenyl)(pentafluorophenylamino)methyl]but-3-en-2-one
• 英文别名: 3-[(2,3,4,5,6-Pentafluoroanilino)-(2,3,4,5,6-pentafluorophenyl)methyl]but-3-en-2-one
• CAS: 851867-22-6
• 化学式: C₁₇H₇F₁₀NO
• 分子量: 431.233
• InChiKey: FYUHSANDMAACND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  3-[(pentafluorophenyl)(pentafluorophenylamino)methyl]but-3-en-2-one 在 三乙烯二胺 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 3-methyl-4-methylidene-6-[(pentafluorophenyl)(pentafluorophenylamino)methyl]cyclohex-2-en-1-one
  参考文献：
  名称：

  An unexpected highly diastereoselective double Baylis–Hillman reaction of per- (or poly)fluorophenyl aromatic aldimines with methyl vinyl ketone

  摘要：

  Aza-Baylis-Hillman reaction of per- (or poly)fluorophenyl aromatic aldimines 1 with methyl vinyl ketone (MVK) was studied. It was found that both the used Lewis base and solvent can significantly affect the reaction. Using triphenylphosphine as a Lewis base, the reaction of 1 with MVK proceeded smoothly to give the normal Baylis-Hillman adduct 2 along with the double Baylis-Hillman adduct 3 as by-product in THE When 1,4-diazabicyclo [2.2.2] octane was used as a Lewis base in DMF, the aza-Baylis-Hillman reaction of 1 with MVK gave the double aza-Baylis-Hillman adduct 3 exclusively in moderate to good yields with excellent diastereoselectivities. The double Baylis-Hillman adduct 3 was conveniently converted to fluorine-containing 4-alkylidene-2-cyclohexen-1-ones under mild reaction conditions in good yields. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.01.130
• 作为产物：
  描述：

  N-pentafluorophenyl-pentafluorophenylaldimine 、 丁烯酮 在 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以80%的产率得到3-[(pentafluorophenyl)(pentafluorophenylamino)methyl]but-3-en-2-one
  参考文献：
  名称：

  An unexpected highly diastereoselective double Baylis–Hillman reaction of per- (or poly)fluorophenyl aromatic aldimines with methyl vinyl ketone

  摘要：

  Aza-Baylis-Hillman reaction of per- (or poly)fluorophenyl aromatic aldimines 1 with methyl vinyl ketone (MVK) was studied. It was found that both the used Lewis base and solvent can significantly affect the reaction. Using triphenylphosphine as a Lewis base, the reaction of 1 with MVK proceeded smoothly to give the normal Baylis-Hillman adduct 2 along with the double Baylis-Hillman adduct 3 as by-product in THE When 1,4-diazabicyclo [2.2.2] octane was used as a Lewis base in DMF, the aza-Baylis-Hillman reaction of 1 with MVK gave the double aza-Baylis-Hillman adduct 3 exclusively in moderate to good yields with excellent diastereoselectivities. The double Baylis-Hillman adduct 3 was conveniently converted to fluorine-containing 4-alkylidene-2-cyclohexen-1-ones under mild reaction conditions in good yields. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.01.130

文献信息

• An unexpected highly diastereoselective double Baylis–Hillman reaction of per- (or poly)fluorophenyl aromatic aldimines with methyl vinyl ketone
  作者：Xinyuan Liu、Jinwei Zhao、Guifang Jin、Gang Zhao、Shizheng Zhu、Shaowu Wang

  DOI：10.1016/j.tet.2005.01.130

  日期：2005.4

  Aza-Baylis-Hillman reaction of per- (or poly)fluorophenyl aromatic aldimines 1 with methyl vinyl ketone (MVK) was studied. It was found that both the used Lewis base and solvent can significantly affect the reaction. Using triphenylphosphine as a Lewis base, the reaction of 1 with MVK proceeded smoothly to give the normal Baylis-Hillman adduct 2 along with the double Baylis-Hillman adduct 3 as by-product in THE When 1,4-diazabicyclo [2.2.2] octane was used as a Lewis base in DMF, the aza-Baylis-Hillman reaction of 1 with MVK gave the double aza-Baylis-Hillman adduct 3 exclusively in moderate to good yields with excellent diastereoselectivities. The double Baylis-Hillman adduct 3 was conveniently converted to fluorine-containing 4-alkylidene-2-cyclohexen-1-ones under mild reaction conditions in good yields. (c) 2005 Elsevier Ltd. All rights reserved.