(E)-3-[anilino(phenyl)methyl]-4-iodobut-3-en-2-one | 915126-31-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (E)-3-[anilino(phenyl)methyl]-4-iodobut-3-en-2-one
• CAS: 915126-31-7
• 化学式: C₁₇H₁₆INO
• 分子量: 377.225
• InChiKey: DBELOOSEIDNICO-VBKFSLOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  20
• 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：
  2

反应信息

• 作为反应物：
  描述：

  (E)-3-[anilino(phenyl)methyl]-4-iodobut-3-en-2-one 在 copper(l) iodide potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 生成 (E)-3-[(N-benzylanilino)-phenylmethyl]pent-3-en-2-one
  参考文献：
  名称：

  ZrCl4-catalyzed X–C/C–C bond formation for the geometric selective synthesis of (E)-β-iodo aza Morita–Baylis–Hillman (MBH) adducts

  摘要：

  A geometric selective synthesis of (E)-beta-iodo and beta-alkyl vinyl ketones (MBH amino adducts) has been developed through a three-component Mannich-type reaction. The reaction was conveniently conducted by generating 3-iodo allenolate intermediates via the alpha,beta-unsaturated addition of TMS-I to 3-butyn-2-one followed by a carbonyl addition onto N-aryl imines in the presence of ZrCl4 catalyst. The resulting beta-iodo allylic amines can be readily converted into beta-alkyl Morita-Baylis-Hillman adducts by performing Suzuki and Kumada cross-couplings. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.08.128
• 作为产物：
  描述：

  3-丁炔-2-酮 、 (E)-N-benzylidenebenzenamine 在 氯化锆(IV) 碘代三甲硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以97%的产率得到(E)-3-[anilino(phenyl)methyl]-4-iodobut-3-en-2-one
  参考文献：
  名称：

  ZrCl4-catalyzed X–C/C–C bond formation for the geometric selective synthesis of (E)-β-iodo aza Morita–Baylis–Hillman (MBH) adducts

  摘要：

  A geometric selective synthesis of (E)-beta-iodo and beta-alkyl vinyl ketones (MBH amino adducts) has been developed through a three-component Mannich-type reaction. The reaction was conveniently conducted by generating 3-iodo allenolate intermediates via the alpha,beta-unsaturated addition of TMS-I to 3-butyn-2-one followed by a carbonyl addition onto N-aryl imines in the presence of ZrCl4 catalyst. The resulting beta-iodo allylic amines can be readily converted into beta-alkyl Morita-Baylis-Hillman adducts by performing Suzuki and Kumada cross-couplings. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.08.128