methyl 4-(2-formyl-N-(2,2,2-trifluoroacetyl)anilino)but-2-enoate | 452322-01-9

• 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: methyl 4-(2-formyl-N-(2,2,2-trifluoroacetyl)anilino)but-2-enoate
• CAS: 452322-01-9
• 化学式: C₁₄H₁₂F₃NO₄
• 分子量: 315.249
• InChiKey: LWTNSSKODUUMSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 4-(2-formyl-N-(2,2,2-trifluoroacetyl)anilino)but-2-enoate 在 吡啶 、 盐酸羟胺 作用下， 以 乙醇 为溶剂， 以65%的产率得到methyl 4-[2-(hydroxyiminomethyl)-N-(2,2,2-trifluoroacetyl)anilino]but-2-enoate
  参考文献：
  名称：

  Synthesis and in vivo evaluation of [11C]MPTQ: A potential PET tracer for alpha2A-adrenergic receptors

  摘要：

  Radiosynthesis and in vivo evaluation of [N-methyl-C-11] 5-methyl-3-[4-(3-phenylallyl)-piperazin-1-ylmethyl]-3,3a,4,5-tetrahydroisoxazolo[4,3-c] quinoline (1), a potential PET tracer for alpha2-adrenergic receptors is described. Syntheses of nonradioactive standard 1 and corresponding desmethyl precursor 2 were achieved from 2-aminobenzaldehyde in 40% and 65% yields, respectively. Methylation using [C-11]CH3I in presence of aqueous potassium hydroxide in DMSO afforded [C-11]1 in 25% yield (EOS) with > 99% chemical and radiochemical purities with a specific activity ranged from 3-4 Ci/mu mol (n = 6). The total synthesis time was 30 min from EOB. PET studies in anesthetized baboon show that [C-11]1 penetrates BBB and accumulates in alpha2A-AR enriched brain areas. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.04.099
• 作为产物：
  描述：

  4-溴巴豆酸甲酯 、 2,2,2-trifluoro-N-(2-formylphenyl)acetamide 在 18-冠醚-6 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以60%的产率得到methyl 4-(2-formyl-N-(2,2,2-trifluoroacetyl)anilino)but-2-enoate
  参考文献：
  名称：

  Synthesis and in vivo evaluation of [11C]MPTQ: A potential PET tracer for alpha2A-adrenergic receptors

  摘要：

  Radiosynthesis and in vivo evaluation of [N-methyl-C-11] 5-methyl-3-[4-(3-phenylallyl)-piperazin-1-ylmethyl]-3,3a,4,5-tetrahydroisoxazolo[4,3-c] quinoline (1), a potential PET tracer for alpha2-adrenergic receptors is described. Syntheses of nonradioactive standard 1 and corresponding desmethyl precursor 2 were achieved from 2-aminobenzaldehyde in 40% and 65% yields, respectively. Methylation using [C-11]CH3I in presence of aqueous potassium hydroxide in DMSO afforded [C-11]1 in 25% yield (EOS) with > 99% chemical and radiochemical purities with a specific activity ranged from 3-4 Ci/mu mol (n = 6). The total synthesis time was 30 min from EOB. PET studies in anesthetized baboon show that [C-11]1 penetrates BBB and accumulates in alpha2A-AR enriched brain areas. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.04.099

文献信息

• Synthesis and in vivo evaluation of [11C]MPTQ: A potential PET tracer for alpha2A-adrenergic receptors
  作者：Jaya Prabhakaran、Vattoly J. Majo、Matthew S. Milak、Pratap Mali、Lyudmila Savenkova、J. John Mann、Ramin V. Parsey、J.S. Dileep Kumar

  DOI：10.1016/j.bmcl.2010.04.099

  日期：2010.6

  Radiosynthesis and in vivo evaluation of [N-methyl-C-11] 5-methyl-3-[4-(3-phenylallyl)-piperazin-1-ylmethyl]-3,3a,4,5-tetrahydroisoxazolo[4,3-c] quinoline (1), a potential PET tracer for alpha2-adrenergic receptors is described. Syntheses of nonradioactive standard 1 and corresponding desmethyl precursor 2 were achieved from 2-aminobenzaldehyde in 40% and 65% yields, respectively. Methylation using [C-11]CH3I in presence of aqueous potassium hydroxide in DMSO afforded [C-11]1 in 25% yield (EOS) with > 99% chemical and radiochemical purities with a specific activity ranged from 3-4 Ci/mu mol (n = 6). The total synthesis time was 30 min from EOB. PET studies in anesthetized baboon show that [C-11]1 penetrates BBB and accumulates in alpha2A-AR enriched brain areas. (C) 2010 Elsevier Ltd. All rights reserved.