(2E)-2-[(2-fluorophenyl)methylidene]butan-1-ol | 866603-48-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (2E)-2-[(2-fluorophenyl)methylidene]butan-1-ol
• CAS: 866603-48-7
• 化学式: C₁₁H₁₃FO
• 分子量: 180.222
• InChiKey: XQJVHCNHTQTGDJ-VQHVLOKHSA-N

物化性质

• 沸点：
  284.0±20.0 °C(Predicted)
• 密度：
  1.092±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2E)-2-[(2-fluorophenyl)methylidene]butan-1-ol 在 titanium(IV) isopropylate 、 palladium on activated charcoal sodium chlorite 、 sodium dihydrogenphosphate 、 四丙基高钌酸铵 、 2-甲基-2-丁烯 、 L-(+)-酒石酸二异丙酯 、 4 A molecular sieve 、 氢气 、 sodium hydride 、 N-甲基吗啉氧化物 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 反应 41.0h， 生成 (R)-(+)-2-ethyl-2,3-dihydrobenzofuran carboxylic acid
  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 、 二异丁基氢化铝 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 14.02h， 生成 (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

文献信息

• Enantioselective synthesis of 2-ethyl-2,3-dihydrobenzofuran carboxylic acid, direct precursor of (+)-efaroxan, from a Baylis–Hillman adduct
  作者：Gabriel P. de Carvalho e Silveira、Fernando Coelho

  DOI：10.1016/j.tetlet.2005.07.099

  日期：2005.9

  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.