(Z)-7-<(tetrahydro-2H-pyran-2-yl)oxy>-5-heptenenitrile | 217454-31-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (Z)-7-<(tetrahydro-2H-pyran-2-yl)oxy>-5-heptenenitrile
• 英文别名: (5Z)-7-(tetrahydro-2H-pyran-2-yloxy)-5-heptenenitrile；(Z)-7-(oxan-2-yloxy)hept-5-enenitrile
• CAS: 217454-31-4
• 化学式: C₁₂H₁₉NO₂
• 分子量: 209.288
• InChiKey: RIWZVGMEJFXPKY-UTCJRWHESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  42.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-7-<(tetrahydro-2H-pyran-2-yl)oxy>-5-heptenenitrile 在 盐酸 、 偶氮二异丁腈 、 苯硫酚 作用下， 以 苯 为溶剂， 反应 6.25h， 生成 (E)-7-hydroxy-1-phenylhept-5-en-1-one
  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：

  (tetrahydropyranyloxy)acetaldehyde 、 (4-cyanobutyl)triphenylphosphonium bromide 在 双(三甲基硅烷基)氨基钾 作用下， 生成 (Z)-7-<(tetrahydro-2H-pyran-2-yl)oxy>-5-heptenenitrile
  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

• Ep2 Receptor Agonists
  申请人：Borman Richard Anthony

  公开号：US20080045596A1

  公开（公告）日：2008-02-21

  A compound selected from one of the following: or a salt, solvate, chemically protected form or prodrug thereof, and its use in treating conditions alleviated by agonism of an EP 2 receptor.

  从以下化合物中选择一个：或其盐、溶剂化物、化学保护形式或前药，以及其在治疗通过EP2受体激动缓解的疾病中的应用。
• 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.