(E)-8-hydroxyoct-3-en-2-one | 172877-31-5

• 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)-8-hydroxyoct-3-en-2-one
• CAS: 172877-31-5
• 化学式: C₈H₁₄O₂
• 分子量: 142.198
• InChiKey: OCLKPVIGROBCFE-GQCTYLIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 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)-8-hydroxyoct-3-en-2-one 在 palladium on activated charcoal 氢气 作用下， 以98%的产率得到1-羟基-7-辛酮
  参考文献：
  名称：

  Stereocontrolled intramolecular michael-aldol reaction mediated with bu2botf and (tms)2nh

  摘要：

  Treatment of keto-esters 1-5 with Bu(2)BOTf and (TMS)(2)NH caused a tandem Michael-aldol reaction to give polycyclic cyclobutanes 6-10 with high stereoselection. It was proved that the reaction was accelerated by the addition of Bu(4)NI.

  DOI：

  10.1016/0040-4039(95)01711-p
• 作为产物：
  描述：

  tetrahydro-2H-2-pyranol 、 1-三苯基膦-2-丙酮 以93%的产率得到(E)-8-hydroxyoct-3-en-2-one
  参考文献：
  名称：

  Stereocontrolled intramolecular michael-aldol reaction mediated with bu2botf and (tms)2nh

  摘要：

  Treatment of keto-esters 1-5 with Bu(2)BOTf and (TMS)(2)NH caused a tandem Michael-aldol reaction to give polycyclic cyclobutanes 6-10 with high stereoselection. It was proved that the reaction was accelerated by the addition of Bu(4)NI.

  DOI：

  10.1016/0040-4039(95)01711-p

文献信息

• Intramolecular [4 + 2] Cycloadditions of Iminoacetonitriles:  A New Class of Azadienophiles for Hetero Diels−Alder Reactions
  作者：David T. Amos、Adam R. Renslo、Rick L. Danheiser

  DOI：10.1021/ja034629o

  日期：2003.4.1

  Iminoacetonitriles participate as reactive dienophiles in stereoselective intramolecular hetero Diels-Alder reactions which afford substituted quinolizidines. The cycloadduct with exo-oriented cyano group is obtained as the major or exclusive product of the reaction as a consequence of the alpha-amino nitrile anomeric effect The alpha-amino nitrile moieties incorporated in the cycloadducts constitute

  亚氨基乙腈作为反应性亲二烯体参与立体选择性分子内杂 Diels-Alder 反应，提供取代的喹啉。由于 α-氨基腈异头效应，具有外取向氰基的环加合物作为反应的主要或唯一产物获得 加入环加合物中的 α-氨基腈部分构成潜在的亚胺离子，当暴露于温和的质子酸或路易斯酸被揭露，为进一步有用的合成转化奠定了基础。例如，使用 NaBH3CN 进行还原脱氰会切除氰基，而 Bruylants 与格氏试剂和乙炔化物的反应会产生 α 取代的胺。
• Stereocontrolled intramolecular michael-aldol reaction mediated with bu2botf and (tms)2nh
  作者：Masataka Ihara、Takahiko Taniguchi、Masami Yamada、Yuji Tokunaga、Keiichiro Fukumoto

  DOI：10.1016/0040-4039(95)01711-p

  日期：1995.10

  Treatment of keto-esters 1-5 with Bu(2)BOTf and (TMS)(2)NH caused a tandem Michael-aldol reaction to give polycyclic cyclobutanes 6-10 with high stereoselection. It was proved that the reaction was accelerated by the addition of Bu(4)NI.