(E)-6-hydroxy-8-phenyloct-3-en-2-one | 1357931-04-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-6-hydroxy-8-phenyloct-3-en-2-one
• CAS: 1357931-04-4
• 化学式: C₁₄H₁₈O₂
• 分子量: 218.296
• InChiKey: TXGKLQUFMLYZBI-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-6-hydroxy-8-phenyloct-3-en-2-one 在 palladium 10% on activated carbon 、 氢气 、 对甲苯磺酸 作用下， 以 四氢呋喃 为溶剂， 20.0 ℃ 、4.14 MPa 条件下， 反应 5.5h， 生成 2-methoxy-2-methyl-6-phenethyltetrahydro-2H-pyran-4-ol
  参考文献：
  名称：

  A Mild, Diastereoselective Construction of Cyclic and Spirocyclic Ketals Employing a Tandem Photoisomerization/Cyclization Tactic

  摘要：

  The cyclization of trans-d-hydroxy enones to cyclic mixed ketals routinely requires superstoichiometric strong acid. By operating under a photoisomerization regime, the cyclization of trans-d-hydroxy enones proceeds under catalytic Bronsted acid to provide cyclic ketals or unsaturated spiroketals in a highly diastereoselective fashion. A one-pot, two-step protocol was thus developed to provide cyclic methoxy ketals with a free beta-hydroxy group for future functionalization.

  DOI：

  10.1021/ol503116q
• 作为产物：
  描述：

  1-苯基-5-己烯-3-醇 、 丁烯酮 在 Hoveyda-Grubbs catalyst second generation 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 3.0h， 以85%的产率得到(E)-6-hydroxy-8-phenyloct-3-en-2-one
  参考文献：
  名称：

  A Mild, Diastereoselective Construction of Cyclic and Spirocyclic Ketals Employing a Tandem Photoisomerization/Cyclization Tactic

  摘要：

  The cyclization of trans-d-hydroxy enones to cyclic mixed ketals routinely requires superstoichiometric strong acid. By operating under a photoisomerization regime, the cyclization of trans-d-hydroxy enones proceeds under catalytic Bronsted acid to provide cyclic ketals or unsaturated spiroketals in a highly diastereoselective fashion. A one-pot, two-step protocol was thus developed to provide cyclic methoxy ketals with a free beta-hydroxy group for future functionalization.

  DOI：

  10.1021/ol503116q

文献信息

• Diastereoselective Construction of <i>syn</i>-1,3-Dioxanes via a Bismuth-Mediated Two-Component Hemiacetal/Oxa-Conjugate Addition Reaction
  作者：P. Andrew Evans、Aleksandr Grisin、Michael J. Lawler

  DOI：10.1021/ja208668u

  日期：2012.2.15

  The bismuth-mediated two-component hemiacetal/oxa-conjugate addition of delta-trialkylsilyloxy and delta-hydroxy alpha,beta-unsaturated aldehydes and ketones with alkyl aldehydes provides the syn-1,3-dioxanes in a highly efficient and stereoselective manner. The key advantages of this protocol are its operational simplicity and its ability to directly access electron-withdrawing groups without recourse to oxidation state adjustments.
• A Mild, Diastereoselective Construction of Cyclic and Spirocyclic Ketals Employing a Tandem Photoisomerization/Cyclization Tactic
  作者：Bo Li、Brett D. Williams、Amos B. Smith

  DOI：10.1021/ol503116q

  日期：2015.1.2

  The cyclization of trans-d-hydroxy enones to cyclic mixed ketals routinely requires superstoichiometric strong acid. By operating under a photoisomerization regime, the cyclization of trans-d-hydroxy enones proceeds under catalytic Bronsted acid to provide cyclic ketals or unsaturated spiroketals in a highly diastereoselective fashion. A one-pot, two-step protocol was thus developed to provide cyclic methoxy ketals with a free beta-hydroxy group for future functionalization.