(E)-7-hydroxy-4'-methoxy-5-heptenophenone | 217454-52-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-7-hydroxy-4'-methoxy-5-heptenophenone
• 英文别名: (E)-7-hydroxy-1-(4-methoxyphenyl)hept-5-en-1-one
• CAS: 217454-52-9
• 化学式: C₁₄H₁₈O₃
• 分子量: 234.295
• InChiKey: VMDATUSMVPDXDI-HWKANZROSA-N

物化性质

• 沸点：
  392.0±37.0 °C(Predicted)
• 密度：
  1.071±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-7-hydroxy-4'-methoxy-5-heptenophenone 在 溴 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以63%的产率得到(E)-7-bromo-4'-methoxy-5-heptenophenone
  参考文献：
  名称：

  Intramolecular Cyclization of Tethered Phenyl Ketones. Complementary Stereochemical Results Arising from the Indium-Promoted Ring Closure of Allyl Bromides and the Fluoride Ion-Induced Desilylation of Allylsilanes

  摘要：

  dThe intramolecular indium-promoted cyclization of 4'-substituted (Z)- and (E)-7-bromo-5-heptenophenones has been examined in aqueous tetrahydrofuran. In every instance, ring closure occurred to deliver the syn-2-vinylcyclopentanol exclusively. The corresponding allylsilanes have been prepared as well, and the course of their fluoride ion-induced cyclization was also studied. In these systems, a kinetic bias for formation of the anti-2-vinylcyclopentanol is observed, although not with the same exclusivity. Accordingly, complementarity in product diastereoselectivity can be realized in purposeful fashion. The data acquired in this investigation suggest that the indium-catalyzed reactions involve intramolecularly coordinated transition states where development of a cis 5/6-bicyclic framework is most energetically feasible. In contrast, the silanes appear to utilize open-chain antiperiplanar transition states. While the latter are not particularly sensitive to double-bond geometry, they are responsive to steric compression involving the aryl group.

  DOI：

  10.1021/jo981683s
• 作为产物：
  描述：

  (4-cyanobutyl)triphenylphosphonium bromide 在 盐酸 、 偶氮二异丁腈 、 双(三甲基硅烷基)氨基钾 、 苯硫酚 作用下， 以 苯 为溶剂， 反应 11.75h， 生成 (E)-7-hydroxy-4'-methoxy-5-heptenophenone
  参考文献：
  名称：

  Intramolecular Cyclization of Tethered Phenyl Ketones. Complementary Stereochemical Results Arising from the Indium-Promoted Ring Closure of Allyl Bromides and the Fluoride Ion-Induced Desilylation of Allylsilanes

  摘要：

  dThe intramolecular indium-promoted cyclization of 4'-substituted (Z)- and (E)-7-bromo-5-heptenophenones has been examined in aqueous tetrahydrofuran. In every instance, ring closure occurred to deliver the syn-2-vinylcyclopentanol exclusively. The corresponding allylsilanes have been prepared as well, and the course of their fluoride ion-induced cyclization was also studied. In these systems, a kinetic bias for formation of the anti-2-vinylcyclopentanol is observed, although not with the same exclusivity. Accordingly, complementarity in product diastereoselectivity can be realized in purposeful fashion. The data acquired in this investigation suggest that the indium-catalyzed reactions involve intramolecularly coordinated transition states where development of a cis 5/6-bicyclic framework is most energetically feasible. In contrast, the silanes appear to utilize open-chain antiperiplanar transition states. While the latter are not particularly sensitive to double-bond geometry, they are responsive to steric compression involving the aryl group.

  DOI：

  10.1021/jo981683s

文献信息

• 10.1021/acs.orglett.4c01969
  作者：Alexandridis, Anestis、Rancon, Thibault、Halliday, Abigail、Kochem, Amélie、Quintard, Adrien

  DOI：10.1021/acs.orglett.4c01969

  日期：——

  newly formed stereocenters. When iron-catalyzed borrowing hydrogen from allylic alcohols was combined with a stereocontrolled organocatalytic oxa-Michael addition, a wide array of chiral tetrahydropyrans were efficiently prepared. The reaction could be performed in a diastereoselective manner from pre-existing stereocenters or enantioselectively from achiral substrates. The key to success was the reactivity

  立体控制的 oxa-Michael 加成具有挑战性，因为该过程具有高度可逆性，最终导致新形成的立体中心外消旋化。当铁催化的烯丙醇借氢与立体控制的有机催化氧杂迈克尔加成相结合时，可以有效地制备多种手性四氢吡喃。该反应可以以非对映选择性方式从预先存在的立体中心进行或以对映选择性方式从非手性底物进行。成功的关键是铁络合物的反应活性，它对烯丙醇脱氢具有选择性，并不可逆地导致反应生成最终产物。
• Intramolecular Cyclization of Tethered Phenyl Ketones. Complementary Stereochemical Results Arising from the Indium-Promoted Ring Closure of Allyl Bromides and the Fluoride Ion-Induced Desilylation of Allylsilanes
  作者：Leo A. Paquette、José L. Mendez-Andino

  DOI：10.1021/jo981683s

  日期：1998.11.1

  dThe intramolecular indium-promoted cyclization of 4'-substituted (Z)- and (E)-7-bromo-5-heptenophenones has been examined in aqueous tetrahydrofuran. In every instance, ring closure occurred to deliver the syn-2-vinylcyclopentanol exclusively. The corresponding allylsilanes have been prepared as well, and the course of their fluoride ion-induced cyclization was also studied. In these systems, a kinetic bias for formation of the anti-2-vinylcyclopentanol is observed, although not with the same exclusivity. Accordingly, complementarity in product diastereoselectivity can be realized in purposeful fashion. The data acquired in this investigation suggest that the indium-catalyzed reactions involve intramolecularly coordinated transition states where development of a cis 5/6-bicyclic framework is most energetically feasible. In contrast, the silanes appear to utilize open-chain antiperiplanar transition states. While the latter are not particularly sensitive to double-bond geometry, they are responsive to steric compression involving the aryl group.