(S)-4-(3,3,3-trifluoroprop-1-enyl)-3-(2-iodobenzoyl)-2,2-dimethyl-1,3-oxazolidine | 781665-43-8

• 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: (S)-4-(3,3,3-trifluoroprop-1-enyl)-3-(2-iodobenzoyl)-2,2-dimethyl-1,3-oxazolidine
• CAS: 781665-43-8
• 化学式: C₁₅H₁₅F₃INO₂
• 分子量: 425.189
• InChiKey: AKGRRVCVUKPJKH-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.99
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (S)-4-(3,3,3-trifluoroprop-1-enyl)-3-(2-iodobenzoyl)-2,2-dimethyl-1,3-oxazolidine 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 以68%的产率得到(10R,10aR)-(2,2,2-trifluoroethyl)-3,3-dimethyl-10,10a-dihydro-1H-oxazolo[3,4-b]isoquinoline-5-one
  参考文献：
  名称：

  Synthesis of 3,3,3-trifluoroprop-1-enyl compounds from some enolizable aldehydes

  摘要：

  2,2,2-Trifluoroethyldiphenylphosphine oxide [Ph2P(O)CH2CF3] (2) is known to give no Homer reaction product with enolizable aldehydes. We found, however, that some enolizable aldehydes such as N-Boc-pyrrolidine-2-aldehyde (9) gave the expected 3,3,3trifluoroprop-1-enyl compounds by reaction with 2. The products could be further transformed to some 2,2,2-trifluoroethyl-substituted nitrogen-containing heterocycles by using radical cyclization or Heck reaction. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.07.030
• 作为产物：
  描述：

  (S)-3-tert-butoxycarbonyl-4-[(E/Z)-3,3,3-trifluoroprop-1-enyl]-2,2-dimethyl-1,3-oxazolidine 在 对甲苯磺酸 、 (+)-10-camphorsulfonic acid 作用下， 以 甲醇 、 苯 为溶剂， 反应 11.0h， 生成 (S)-4-(3,3,3-trifluoroprop-1-enyl)-3-(2-iodobenzoyl)-2,2-dimethyl-1,3-oxazolidine
  参考文献：
  名称：

  Synthesis of 3,3,3-trifluoroprop-1-enyl compounds from some enolizable aldehydes

  摘要：

  2,2,2-Trifluoroethyldiphenylphosphine oxide [Ph2P(O)CH2CF3] (2) is known to give no Homer reaction product with enolizable aldehydes. We found, however, that some enolizable aldehydes such as N-Boc-pyrrolidine-2-aldehyde (9) gave the expected 3,3,3trifluoroprop-1-enyl compounds by reaction with 2. The products could be further transformed to some 2,2,2-trifluoroethyl-substituted nitrogen-containing heterocycles by using radical cyclization or Heck reaction. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.07.030