methyl (2E)-2-[(2-fluorophenyl)methylidene]butanoate | 866603-46-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: methyl (2E)-2-[(2-fluorophenyl)methylidene]butanoate
• CAS: 866603-46-5
• 化学式: C₁₂H₁₃FO₂
• 分子量: 208.232
• InChiKey: NBUMRGYAXWZYBE-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 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：
  3

反应信息

• 作为反应物：
  描述：

  methyl (2E)-2-[(2-fluorophenyl)methylidene]butanoate 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以85%的产率得到(2E)-2-[(2-fluorophenyl)methylidene]butan-1-ol
  参考文献：
  名称：

  Enantioselective synthesis of 2-ethyl-2,3-dihydrobenzofuran carboxylic acid, direct precursor of (+)-efaroxan, from a Baylis–Hillman adduct

  摘要：

  We describe herein a new and straightforward enantioselective approach to R-(+)-2-ethyl-2,3-dihydrofuran carboxylic acid, the direct precursor of (+)-efaroxan, an alpha(2) adrenoreceptor antagonist, which is indicated to be used for the treatment of neuro-degenerative diseases (Alzheimer and Parkinson), migraine and type Iota Iota diabetes. Our goal was accomplished using a Baylis-Hillman adduct as starting material. The dihydrobenzofuran acid was obtained in eight steps with an overall yield of 14%. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.07.099
• 作为产物：
  描述：

  (+/-)-methyl 2-[(2-fluorophenyl)(hydroxy)methyl]prop-2-enoate 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.02h， 生成 methyl (2E)-2-[(2-fluorophenyl)methylidene]butanoate
  参考文献：
  名称：

  Enantioselective synthesis of 2-ethyl-2,3-dihydrobenzofuran carboxylic acid, direct precursor of (+)-efaroxan, from a Baylis–Hillman adduct

  摘要：

  We describe herein a new and straightforward enantioselective approach to R-(+)-2-ethyl-2,3-dihydrofuran carboxylic acid, the direct precursor of (+)-efaroxan, an alpha(2) adrenoreceptor antagonist, which is indicated to be used for the treatment of neuro-degenerative diseases (Alzheimer and Parkinson), migraine and type Iota Iota diabetes. Our goal was accomplished using a Baylis-Hillman adduct as starting material. The dihydrobenzofuran acid was obtained in eight steps with an overall yield of 14%. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.07.099